Matt Roberts was the last head writer for Late Show and he feels fine

all right y'all thought that I might be fibbing this is proof right now the Letterman podcast we have one sponsor one sponsor only but it is Rupert G in the hello Deli thank you very much for sponsoring our show Rupert it's my honor Mike welcome to the Lettermen podcast my name is Mike Chisholm okay we got a great one here um and and I I it didn't take me long to debate whether I should split it into two parts or not I'm not going to we go long form on this show I'm certain at some point we will start clipping things out and and throwing things up we've experimented a little bit with it um there are now technology and tools that make that a lot easier so I'm certain that'll start happening soon but um this episode is so good that I'm like two hours and 45 minutes of content yep let's just do it people can uh Power their way through it throughout the the day or the week or whatever it is that they do but I know that a lot of people are going to listen to it end up listening to it in one go because it's so compelling I'm I'm so excited about this episode I'm excited about them all I know that but um today we got Matt Roberts and and Matt was uh the last um head writer of Late Show with David Letterman um he worked his way up from an intern all the way uh back in the late night days uh all the way through the system and had many many many different positions a lot spent a lot of time as a segment producer a writer um and ended up as the last head writer for the last few years of Late Show this was a fantastic conversation and I'm so grateful uh that I had it now it wasn't just me Don Giller was here as well Don asked some very cool questions pointed out some very cool things and actually had a very sentimental heartfelt moment right near the end that I was not prepared for um because you know Don Giller is known for many many many things expressing sentimentality outside of his compilations uh uh might not necessarily be one that people think of immediately when they um when they think of Dawn and and uh there's a really cool moment in this episode um I just mad as a prince um tell a couple little little inside baseball Tales uh when we were at uh at Chucky's Memorial I saw Matt there and um I I didn't want that to be a place where I tried to you know meet all of these people that I was interested in meeting but there weren't many people um at the top of the list like with Matt Roberts that I wanted to actually go over and introduce myself to and and say hi to thank thankfully uh shortly thereafter I was connected with Matt and um this guy is awesome he's special uh I I love the fact that he was such an Enthusiast of the show um took that enthusiasm aside so he could do the best work that he could for the show so I mean he was still obviously enthusiastic about the show but he couldn't view it the way that he viewed it as a fan per se and uh just professional um the skills that he learned throughout it I I can only imagine how some of the executives who were there longer than Matt saw some of these people coming up through the ranks and and how they finished the show um with the crescendo that was the last six weeks of Late Show um and then of course the Legacy afterwards and and where these people ended up and how they ended up and how proud they were we go through a range of topics throughout this episode uh surface and very deep as well um you know Matt gets really personal about um his time there and I I'm I certainly don't want to sum that up in any way or tease it you're just gonna have to folks that wanna want to watch or listen uh please do in fact let's get to it uh we'll just one more thing the Letterman podcast has one sponsor one sponsor only and that is Rupert G in the hello Deli now Robert Gina hello Deli are in flux right now the place is for sale that's been announced things are happening and the deli is actually closed right now where it's not closed though is hello dashdeli.com you can still get official Late Show with David Letterman merchandise you can get mugs you can get hats you can get shirts um all of that stuff and uh I would recommend doing that just because we don't know what's going to happen when the sale is complete I spoke with Rupert on the day of me shooting this intro here um and he said well you know what when everything is allowed to be announced he's gonna announce it here so that's kind of neat um but it's also kind of Bittersweet as far as I'm concerned I'm sure many of the people who view or listen to this uh this program would feel the same way that being said Rupert we love you so grateful for you as long as hellodashdaily.com exists we're going to be sending people there uh because where are we going to get our Letterman merch otherwise I mean come on let's make it happen so that being said the Lettermen podcast is extremely proud to present former head writer and many more things Matt Roberts okay Matt I uh you know how excited I am about this I know that through the ones and zeros you can feel the uh the the enthusiasm and puppy dog like like love that is happening right now I want to go through just really quick uh the order of positions that you had with pants starting it starts at intern right that's right I actually got to work at the uh at late night as an intern uh in the summer 1992.

okay uh so it was the very last summer day was at NBC so all the stuff was going down behind the scenes of course I was uh oblivious to it all but um but uh yeah summer of 92 I was an intern uh I went back to uh school I went to went to Bowdoin College in Brunswick Maine went back to Bowdoin for my senior year um and graduated and was foolish enough to just think I think they liked me as an intern I'm pretty sure they'll hire me back and it it it was my dream job it was all I ever wanted to do so I kind of thought like once I got the internship there was some part of me not that I thought I deserved it in any way or anything else but there was some part of me it's just like oh yeah I think I think now I mean the hard part's over right the rest of this is gonna work out okay and uh so ignorance is Lovely isn't it it's a wonderful thing being like a sort of stupidly confident 20 something and so um you really have to embrace it um so um so you know there was a part of me that was like well you know if if it if they don't hire me you know I'll work at like I don't know maybe I'll go into radio that was something I liked or whatever but but I just sort of thought no I'm gonna move back to New York and then I'm gonna uh uh they're gonna hire me and so I I I I'm already breaking off into a story I haven't even answered your question but I'll just that's okay I'll tell this quick story and then it will continue on so um so I moved back to New York and I'm in a one of these situations where it's a place that should barely be lived in by one person and there are three of us sharing it and it's in Brooklyn and this is before Brooklyn was even remotely cool um and uh so it's you know um it's a very shady situation where like the landlord makes this pain to his mother across the street and uh and and if we want cable don't call the cable company he'll work it out for us that kind of thing um so um coming from Maine that is fantastic isn't that the New York experience that you would hope is the case like but I didn't have that much of an edge so it all just kind of made me very nervous I'm just you know I was raised in the midwest so I was raised with like a you know everything was like do you have insurance on that you should probably get that insured you know everything was like oh what could go wrong what could you know um so uh so anyway I moved to Brooklyn moved in with my I remember I left College I got you know graduation money and stuff like that I remember my bank balance was it was four figures and it started with a two that's what I remember I moved to New York with Roland in it 2 000 and change right and that was for everything that was rent that was student loans that I had to pay off that was like that's everything it was a poor plan let me just tell you but um it was no plan but so the first like I don't know I'm there for like a month and it's announced that Dave's move well it had already been announced Dave's going to CBS whatever and I get a call and it's a they're hiring for the mail room because of course at NBC NBC had a mail room right a central mail room but now CBS they'd need a mailroom person so they said would you uh would you be willing to come in an interview for the job I said absolutely I went in I interviewed for the job I uh I thought well this is I mean this is it this is how it starts this is a storybook I get the mailroom job right yep and then I get a call back I go in I think I kill it and then I get a call back and they're like ah you know we we really would have loved to hire you but um we hired another former intern who had previous mail room experience oh my gosh I think I can say was Cheryl zelickson who worked at the show also for its entirety starting in the mail room and ending up as a um I'm gonna get her Talent wrong or her title wrong rather but she works in the talent Department uh booking music acts and producing music acts and um uh I think maybe music segment producer but I'm sorry if I'm getting that I may be understating her title I I hope I'm not but anyway she was there for the whole run as well so we were my um uh uh sorry here uh don't be uh my computer just did something weird uh so my uh uh uh uh uh my so so then we got to be like August we got to be uh uh uh uh August maybe Late July we'll say later July because they're showing are you coming close to the premiere of Late Show that's right it's like Late July and I'm realizing I don't have enough money to stay in New York uh Beyond like I I can maybe make it to August but I probably can't make it to August and I had even gone and I looked at jobs the only uh uh the only uh uh work experience I had was uh in retail I had done retail jobs in college I worked at like the Gap I worked at Brooks Brothers I worked at different places and uh so I uh uh I thought you know what maybe I should just buy my time and I'll go get a retail job and then when I applied for a retail job and I got it and the morning that I was supposed to go in I realized you know what I'm I'm not going to be able to live New York on a retail job like I'm not going to be able to afford like my student loans every you know all this stuff and uh so I called him up that morning and I said I'm really sorry I don't mean to do I'm sorry to be last minute on this but I I I'm just not this job is not going to work out for me I'm not going to take the job it was like training it was going to start training that day or whatever and I was like I'm just not gonna not going to be able to do this and so I hung up the phone I called I got up early to call them and let them know and I hung up the phone and I think I went back to bed and the phone rang like an hour later and it was a Letterman show calling to tell me that they needed a uh uh someone in the ticket office wow and could I come in for a ticket office interview and uh so truly if I had gone it came the call came at a time when if I had taken the job I would have been on my way to that job would have missed this call like I'm sure we had an answering machine or something but you just kind of go like yeah but would they have called me back would they've had enough people so anyway that was that was a very long-winded answer we've got about time for One More Story Mike but um but but hey man I just thought you had an answering machine and it wasn't stolen at that point um okay so I host a men's mental Wellness podcast as well that's where I got my podcasting chops from and so I like going back and looking at those little moments those little moments where where you don't know this until reflection like this and I think a reflection like this is important where it's like these are these you know lightning strike moments of Our Lives where an entire pathway or Direction could be in the balance of things and and you doing that I mean you think of the Serendipity of of you actually having because you had no plan up to this point why is this the point where you know critical thinking shows up that's right and it's the moment where an hour later your life actually does put you back on the path that you truly your hearts desire and I just I I find that delightful so yeah that's that that's a fantastic story I love it that's right well thanks I mean it was it's one of those things where yes you look back at that that and also you know you look back at people the same way you know I look back at people whose interaction with me um got me you know got me to The Next Step where whereas I might not have been able to make that stuff had it not been for that person going out of their way uh you know Dan Kelly talked about on your show yeah yeah Steve O'Donnell for for Dan kellison like was was one of those people and so anyway there there's so many you know so many places like that where you you know sometimes it's just dumb luck but oftentimes it's other people's kindness uh and going out of their way for someone who's coming after them that uh makes all the difference you know uh yeah you're preaching to the choir on that so so anyway to finish answering your question just to lay out a framework so it was intern yep uh ticket office yep uh researcher Talent researcher then a segment producer uh then uh then these things start to sort of overlap I produce segments for about 13 years but about four years into producing segments I was made a producer and a writer yes and then I guess at the end of those about the end of those 13 years I was made executive producer and then uh for the last two-ish years of the show I was the head writer so that's the and then oh that was a supervising producer title in there somewhere but I mean it was you know it just reflects sort of more responsibility and more you know just a seniority kind of thing at the show certainly um you were the last uh writer for Late Show with David Letterman yeah yeah that is unbelievable um and so for each one of those positions that you had each one of those eras and don't get me wrong I don't want to focus each episode on one but I I would like an episode for uh each one of the eras that you did have I would like to have you go on as a guest because again just like when you did your staff moments I mean how do you have one of these moments where Walter shows up and you try and boil it down and I I feel bad for him trying to edit some of these people because the memories are so vast and the the breadth and the depth of that is just in incredible um I'm I'm so grateful that uh that we can do this first one here but don't get me wrong I'm going to be come back called because I know you have uh nearly Limitless amount of of stories and appreciation you know most of the people who worked at this place um you know for a long period of time there became a culture it was a family I I love that about this uh I'm gonna go into something right in the middle that you said that I find fascinating that seems to be a trend folks who did not set out to become comedy writers end up becoming comedy writers because they're immersed within the culture they find the voice you're already self-deprecating just like the rest of the staff seem to all be um the the culture of the voice all this sort of stuff and then they find themselves becoming a writer for the show at bare minimum people who get you know things onto the top ten somebody who comes in uh studying English not necessarily going to be a comedy writer ends up being the last head writer for David Letterman um was there any in the fantasies that you had coming to work for Dave were there any of them where you were going to be a top-notch comedy writer or heading up a team of cop-notch Comedy Raiders well um I I being a writer was what I always wanted to do I mean even when you were saying abusing you wanted to move over yeah and I guess what I would say about that is you know well a few different things I'd say number one for me the the the desire to work at the show was not a desire to work in TV it was a desire to work for Letterman yes uh and and so I often tell people you know and it was an interesting thing sort of coming out of it in 2015 because I I you know there's a lot uh uh there's a lot of great television out there but there's but but I feel like in the arena that in which the Late Show existed at least to my mind this is just me talking but that's the only one that matters when I'm deciding what to do in my life um is that like I feel like I had the best version of it so to come out of Letterman and do uh you know to to uh you know it was hard to think about maybe just going and working on another talk show you know um and uh uh so so so you know I know and so I often tell people like if Dave had been writing a magazine when I was 11 if he had been the editor-in-chief and created this like Spirit of a magazine I'd probably be in magazine publishing by the time I'm 44.

right because I have wanted to go work for that magazine so to me it was all about that his sensibility you know just his just you know it was just part of the club he brought to it yeah yeah being part of being part of that organization and also watching you know it's all the things people loved about that show it was Clubby it was seeing a bunch of people that looked like the you know looked like people around my house or whatever who were all working on this cool show and having a great time and so yeah so that you know that was um that was a part of it the other part of it was I you know I think the reason I was made as segment producer is because I think I brought uh uh I think I you know it's like one of those things where they say take take a job and and and reframe it around your strengths or focus it on your strengths right I mean to me this the things I love the most about uh producing segments were when I could help make someone be uh uh funnier you know and I I mean that the goal was to help make the experience more positive for everyone right for Dave and for the guest right and and and it was really important to Dave that Dave wanted the guests to shine right I mean he wanted them to come out and be he wanted to be able to like hand off a a an introduction to a story for them and have them just like drive it home like he didn't have to be the one getting the laughs he you know so um uh so you know I think part of what uh I enjoyed the most out of segment producing was crafting the intros or helping reframe stories for guests in a way that they realized they they might have just had one funny thing to say about uh a trip they were just on or something like that but it was funny enough that you go like all right that feels like a complete payoff to uh to uh to an area so if I can get a couple funny takes on something even from them to build up to it if you had like a little laugh a little laugh and a big laugh well then that kind of makes an area you can get something out of that you know so it was a it was it was sort of that um Alchemy is too strong a word but it is sort of I was going to use the word alchemy I was about to use that word that that's that's it that's totally it there's some sort of virtual Alchemy happening right here I guess but uh there you go so that's what that's that's that's you know that was the goal and so um you know uh uh uh yeah I mean that was that was uh that was why and in fact you know again I'm gonna reference uh Daniel kellison's conversation with you but you know he referred to the fact that he had gotten offered uh a job on the uh or wait was it no no it wasn't kelison I think it was uh lee Ellenberg who was talking about getting getting offered a job on uh the 12th floor receptionist and you don't even want to be you don't even want to be associated with the the production floor and even as a receptionist because you're afraid you'll get siled and every it'll be like oh no he's a production guy he answers the funds on 12.

um so there was a part of me that really um uh you know that that paused about taking the segment producing job but the thing about the second producing job was I was 25 years old I'd been at the show three years at that point um not counting the internship an employee at the show at three years and a segment producer a segment producing job meant you had FaceTime with Dave every single day you're going into his office and you were talking through the segments with him uh or you know or you were talking to him across the desk in the studio or you were and so I just thought well there's the value of that supersedes um anything else I thought if I'm Gonna Learn how to uh you know if if if I've got a future with the show and I'm going to learn best how to do it I'm not going to learn any faster than I am from Dave directly right um so uh uh yeah so that that's uh you know that was you know for a 25 year old because you know we all remember uh those of us who are men who who once were 25 year old men we remember uh how how how uh shockingly little critical thinking that we do have at that age that is actually a very um you know that's very astute thinking about that going okay you know what and it reminds me of when when Casey was on and and you know Casey has gone on and to do some great things in television and whatnot and how you know starting as Dave's assistant being right there having to write these letters for Dave having to write the letters in the voice and and and and and knowing these the things that she learned there without even necessarily knowing that she was learning them uh again yeah to wait to bring it back around to you uh being a segment producer to to be able to do other things in the show um that that did have the most precious thing about that show was the voice and and having you know face time with Dave there aren't a lot of staff staff members who can say that there's so many staff members who say the opposite you know I worked there for x amount of years and I saw them you know I get on one one hand how many times I actually saw saw him you know and that's just you know fascinating parts of the show here um I gotta ask real quick uh any notable lines that you threw somebody so you're sitting down with somebody they're telling you the anecdote they bring and you're like okay well at this point here you could throw this one out there I can only imagine there'd be a special kind of Joy or satisfaction when panel is happening and they throw the line out with the right timing and stuff and it gets a big laugh anything that comes to your mind when I say that um you know I'm conflicted because to be honest with you I mean it's it's hard to want to give The Magicians tricks away is that what it is well no no it's not about giving The Magicians tricks away it's just I I I it's just I hesitate to to um showcase um myself in the context of funny people who bring 90 of their own funny material and then I go but I gave them this so oh so yeah okay that's my only hesitation in doing that okay to be honest with you I can't you know it's it's like one or two examples I'm thinking of but um but you know as far as collaborations go though like I would say like uh you know and I I I don't feel bad about you know he's very generous uh about saying this or actually both these guys uh you know uh Martin Short and Nathan Lane are two guys who I really just clicked with um and obviously revered both of them but uh you know it's that combination of things you have to like you know when you know you you you have to find someone it's the what is it called the double coincidence of once in um in economics I think uh um but anyway uh um you have to find someone that not only you really really like and love writing in their voice but they also like you and think you can write in their voice so um so you know it was that but you know so uh with uh you know with both Nathan and Marty like it was a lot of back and forth and again I give them uh you know beyond the line and share the credit and plus by the way um uh and and they're both very gracious guys who uh were are Pleasant you know are Beyond Pleasant to work with but are also just uh super kind about giving um giving credit where they certainly don't even need to um and uh but but you know we would we would have a great time collaborating um uh on on segments and and I just I love it I love a a funny an unbelievably funny person who can write it's hard to kind of beat that and that's I mean that that's what you know Letterman was as well obviously uh you just also name two people who um you know from from everything I've heard and you'll have a really good perspective on this as well uh the best guess you know obviously um you know the level is high Dave's expectation is high not just day but the entire Show's expectation for these segments are high I want everyone to shine as you said earlier we've talked to so many people who have talked about how there are certain guests who knew they were coming on panel um you know guess who who understood uh that the spontaneity was very well planned and and and and spontaneous on spontaneous uh well plan spontaneity great but very well planned to make it look spontaneous many times and some guests got that you know the Steve Martin's The Bruce Willis's of the world uh Nathan Lane Martin Short both very very much examples of that because a lot of the time you had songs and and production involved with their appearances uh sometimes going back you know let's plan this for a couple of weeks here um were those was your favorite were those the ones because I mean you're sitting there producing a show tonight where you've got maybe you know 45 minutes to figure something out with tonight's guest but then you've got someone for two weeks from now who wants to plan something a little more ornate uh that's just part of the fun of the job I guess right oh yeah and I mean it was always it was always fun when a guest wanted to do you know when guests wanted to do more and make it an event you know and that was another great thing about you know Dave and the show is it was like you know some some shows um you know might want to you know make it more about the host or not want to take us take attention off the host or whatever else and it was like no if we we were thrilled when guests wanted to do something extra you know and so so as however we could put resources into that you know we would um and so uh yeah Bill Murray Steve Martin Marty Short I mean the list goes on and on Nathan obviously Ben Stiller you know uh Will Ferrell um so uh you know uh a lot of a lot of of extra stuff um so so uh uh yeah I mean of course I love that stuff I love that stuff I mean I it's funny working on Martin Short segments like I would um I would often sort of have a have one of those you know out of body moments where you sort of objectively looking at everything that's going on and when I was in when I was at Bowdoin College um I spent a lot of my free time in the college radio station right and it was because it was in part because I was into like the music of the time but it was mostly because I was creating I loved creating like Jingles or little bits that were like that that you'd put on what we called a card which was an eight-track tape yep and it was a so a loop of tape so it'd be 30 seconds or minute cart and you'd make a little promo for the radio station that was like its own little radio player its own little jingle or its own little whatever yep and I would uh you know I'd grab a friend or two and we would write these things and and produce them and we had no equipment whatsoever I mean it was one of those things where your timing Q you know you're queuing up a sound effect on an on an LP you know I mean it's that kind of thing where it's Precision was difficult but um but uh and you've got all your mixes up at once because you can't do anything like you know you're playing a uh like a bed of music off of a cassette and then you get your sound effect Hue on an LP and then over here you've got some of the so it was uh it was primitive at best but we produced some really fun stuff and so when I was working on a Marty short segment at the Letterman show and we had you know dancers and Pyro and the the the scenic people have built some fabulous set and you know the graphics people were doing some amazing cool thing with last minute instructions that you know they were able to pull out of a hat because they were brilliant um and you know you've got Jerry Foley who's you know got a billion years experience doing like you know pulling this all together in a in 40 minutes which is should be possible um so you know all that stuff happening um I just would think like this is just this is just the version of this is this is wblr at Bowdoin with money that's what this is and talent and extreme Talent obviously but but I mean it was just like wow this is this is just you can draw like it's not really a straight line it's a very like circuitous curvy line but it's definitely a line that connects that experience that I had as a kid basically and this thing that I was doing you know now in my mid to late 20s uh and and Beyond so we just had a guy I don't know if you'll remember him or not your path actually your path might not have crossed uh there was a guy who was um the assistant he was an intern for Paul Shaffer back in the day named Andy Carson um you you probably came into late night maybe a year after him Andy spent uh basically a an extended summer uh as an intern uh you know and and worked with Paul and and all of that well for 20 something years he's been in Oregon he's you know co-hosting a show doing the weather uh you know uh Andy's Adventure segments and things like that in a in in an affiliate in Oregon and has had so much fun because you know and and just the joy of it like what you're talking about here it's all the same thing it's just at different levels of it but the joy is the same joy and um and and he's just loved working in television and he got his start again like you're talking about here at the highest level so he's able to see kind of what this Joy is but the joy Joy is Joy it's the same thing and uh 100 yeah it comes together like that when a team does something and it all comes together the relay race of okay I maybe produce this now what's the director gonna do with it or what's the host gonna do with it or what's going to happen and what does it turn into after that it's like a flower blooming right and um yeah and it just as you're telling me that uh it reminds me of of what Andy talked about um Okay so I want to stay on segment producing before I've got so many things that they're all just kind of colliding like asteroids uh right now in an asteroid field but um let's say with segment producing here for a second um as you got that that gig because research is one thing your time at research the kids today who you know stumble upon this conversation when they do research they have no idea like they just don't understand what research today is versus what research when you were doing research was um you know Dave Dave in his uh in his last speech talking about the Subterranean uh place that the researchers would be in and I mean you you researched out of books right like that's you know you you didn't go the internet wasn't really a thing at that point um like it was stone tablets we've used oh no say yes books the CBS Library uh the New York uh there's like a Performing Arts Library at Lincoln Center that sometimes we dig through there looking for uh footage and audio the Museum of Television radio like uh and then you know uh uh Dan Callison referenced uh Lexus Nexus which was the closest thing you had to an internet search which was a database of articles that had been entered into a a a big thing but you paid like a fortune for it I mean it was it was so we had to like sort of learn like it was like search string optimization for Alexis Nexus so that we could get like a a certain breadth of Articles and um but uh you know if you typed in you know if you typed in Neil Armstrong Moon you know you were gonna get like a billion articles so you had to come up with a way of like you know how are we going to get if we have a big star on how are we gonna get like you'd search by within a range of dates you'd search you know you'd narrow it all down to try to like sort of handicap it but you know yeah uh but that being said on paper again with the with the aid of reflection um it seems like a good segment producer uh in the making is somebody who knows how to do the research to think around corners to know the exact right if you're sifting through all this data that you're talking about here being able to find that little gem that can then you know blossom into uh into a good segment a good story a good whatever plus whatever you know the the principle is bringing with their uh you know their current life of course as well but it seems to me like a good researcher could evolve into a good segment producer I'm onto something with that yeah I think you are well also it you know certainly that also you know as I worked as a researcher under Dan kellison and Mary Connolly and wow they were very encouraging to all of us about like if you have an idea for a funny intro feel free to include that in your memo you know to us and um you know they uh in some ways you know it's on you know on a good day we could be like sort of almost like an associate producer to their segment producer you know an associate segment producer their segment producer we'd we'd kind of get to Shadow them or be with them if they had like extra things they needed to get done we'd be the one they counted on to like sort of close the circle on things right so um uh so in a way you were also getting to um you know it was a little bit of like an apprenticeship depending on how now Daniel I mean very very much felt like an apprenticeship with Daniel because um he referred to me which I choose to think of as being an affectionate thing but other people in the show I think were bothered by it on my behalf because they felt like it was pejorative but I don't think he would call me Junior and so it'd be like a junior where did you put the thing and um always made me laugh but I think that's also because I knew uh I knew uh where Daniel was coming from on it and he was he was such a good Mentor to me and uh in in many ways both like in you know in as a in becoming a segment producer but also just like on a human level uh as a guy who was uh you know kind of getting his uh getting finding his sort of place in New York and everything else um he was really really good to me yep he uh I just appreciate him so much he's the one that uh it's funny because O'Donnell you know saw something in him and brought him in he's the guy that actually connected me to O'Donnell uh so you know these things are all uh you know connected in in so many ways being connected to the central concept which is giving people a hand up and how for whatever reason sometimes there was somebody wherever there was a connection uh made whether it was during an interview you know we talked about Chucky and he brought in so many interns and things like that that ended up doing some major major things within the worldwide pants family um you know obviously he's one of the guys that did that for you and and to the point where you know you're you're this uh well let's say a dynamic duo a Batman uh Robin type situation here uh I wouldn't go so far as to say you were kellison's Ward although we'll uh we'll ask him about that and see what he says about that um who are some other folks that you uh that that you felt felt did that for you and helped bring you love it's it feels like it was part of the culture and many times uh it was it was something that was uh if not hitting home runs every single time it was the goal uh that that that's what people did for each other within the pants family is that is that accurate oh my gosh yeah yeah I mean so many so many people there um you know Maria Pope first and foremost was we know when I when I became so so the timing of things was such that uh Dan left the show to go produce Rosie's show right so he left the show and then and Maria Pope filled that opening she moved over she had been working with the writers as their segment producer basically um and uh so she would produce the pieces like you know Dave's mom at the Olympics and stuff like that that's that that was her like you know uh her area of of specialty yeah and and and then everything that was going on in the daily shows as well but like you know she would also be in charge of these massive Endeavors uh producing them as well but so so she moved into that position um that that opening that Dan left and of course at the time I was you know I mean I I had only been a researcher for two years but I still sort of felt like oh but Dan was my champion and now he's leaving and now I'm not getting that spot and I thought oh well you know oh better luck next time I guess kind of thing you know I mean it wasn't like again I sort of thought like uh you know I had my eye on being a writer anyway so I sort of thought well it's okay you know but it did just seem like it was it felt like based on everything I was doing that it really felt like it was right there and then um uh it was only a matter of I don't know we'd have to check the paperwork but like uh Mary Connolly left only a matter of like a few months later I think it was or maybe maybe that's maybe that it wasn't quite that quick but she left like a few months later and so then they uh you know they were sort of talking about filling uh her her spot and so um so you know I threw my hat and the ring for that um and when I got that now I'm I'm retracing my steps and finding out where I went on this tangent but but when I when I moved in that position like I don't know that there'd been a I mean I don't know how young Dan was when he became a segment producer but I mean I felt like I was pretty young to get that job I was 20 20 25 I guess and um uh you know it is it was a big responsibility it's basically like you know for the most part it's and I think Rob Burnett might have explained it to me this way he said basically it's like you know it's one of the rare positions on the show it's like it's almost like the head writer is to Comedy it's like yes it's it's the ideas it's the material and then there's one person between all the material and whatever's going on and Dave and that's you and then and then it's pretty much to the air so um uh so you know it was uh it was it was a lot and so when I moved into that position I was kind of as green as green could be and Maria Pope uh was so just so good to me I mean she and I are like the closest of friends today um uh and uh but she just I mean we and we went on to just not only just like collaborate on pretty much each other's segment like if there's anything that it sounds even remotely like I'm taking credit for during this conversation just know that there's like a uh an Anne Maria Pope on pretty much uh you know almost all of it I mean I gotta say you could pretty much say that as a blanket statement we we put our heads together on on everything so um uh you know I can't overstate enough how much how valuable that was to me I mean certainly to certainly to sort of come into my own as a singer producer but then beyond that just we were just kind of inseparable through through the end and now through to this day and then the other person who I'd be remiss I mean uh uh Jude Brennan incredible to me and also just just uh just kindness personified and and also just very just smart really thoughtful uh very funny too of course I guess that goes without saying but you know she was amazing and she was somebody who always kind of no matter how um no matter how panicked you could be about something that isn't really life or death but we could get pretty panicked like uh you know she was always somebody who could kind of like be a voice of reason and Barbara Gaines was like a big sister to me and it is to this day uh again I feel like um uh you know Barbara looked out for me and and and and uh and supported me in all sorts of ways and uh it was uh yeah I mean and again personal and professional and just you know more than I could say you just named three women who uh who who I want to talk to very very badly um because so many people have said so many nice things about these people and and I I love hearing it um from your perspective uh you know because at the end of the day it feels like again you're the guy I want to go back there is something with segments that I want to go back to here before uh before but I I do want to note this the idea that the kid you know the kid who was the intern that got hypnotized ended up being the final head writer uh for this show and and so many people who were so much older helped bring him to that place you could see the pride like you could just see the pride that when when when when that when that person on the staff gets him to the ball and I'm not saying that every young person who was given a shot was able to carry the ball as far as they would have maybe liked but you certainly did um the fact that you got to bring it you know and they got to see you shine that way at that point uh is delightful to me I love that okay so simultaneously we're gonna see how well Mike can multitask here Mr Giller is uh coming into the uh to the room here ladies and gentlemen he's gonna love that um and well okay so we'll see while he's connecting to audio but I do want to go back out of here he's got to hear the Applause I want him to hear it all right he answers the room otherwise it's not a very good play on it oh no he's popping in there he is oh my God now does he have his audio up can he hear okay Mr cheerful himself hello Mr Giller how are you you said you said 10 o'clock did I I don't think I did but uh perhaps I mean the good news is Don I've said nothing of any import at this point so you've missed absolutely nothing when you go back and watch it you'll go thank goodness I missed that hour I'm gonna go back to sleep yeah um yeah I interrupted you guys and I apologize for that no no you you didn't you timed it beautifully you did I can't I um I fell asleep at 8 30 this morning so I'm kind of not here um I am interrupting so I'm gonna I'm gonna uh you come in anytime you want Dawn's in the iPad but he's also with us as well and I'm sure he'll I'm certain he'll pop in again before the the conversation's over it's nice to see you man yeah it's nice um what time is it where you are Matt I am in uh London England it's about 10 minutes to three okay all right um I'll put that in the log uh does that help you somehow oh if you feel more awake now that it's mid afternoon here my day is made um yeah uh so long I'll be here but I I'm not here but okay thank you pour yourself a steaming hot pot of coffee is and uh you know and uh and join us in a minute okay yeah no I was trying to remember the second part of that what was that the that was one of those things Dave used to say on the old late night show I feel like when uh uh it was a poor uh poor the kids was it was it wake the kids hot coffee was that what it is well this is this is a Dave thing I remember he used to say something about Pork yeah yeah uh call the neighbors or something like that all the neighbors but I also I thought at one point he used to say Wake the kids and fill them full of hot coffee yeah there was someone like that I'm not if I'm not mistaken I don't know that's what I was trying to recall but anyway I was gonna pull a shaky joke but I figured nah not in good taste um okay uh uh yeah later and I hope uh yeah let me let me uh compose yourself my friend we're all good uh continue on thanks okay I am not cutting a second of that um that was our own sort of guy under the sea the seats appearance right there it was the guy under the virtual seats coming up there our audio listeners may want to watch the Youtube at least for that uh for that part anyway or you can you can Dub Yourself in going what's happening is the Don Giller is appearing slowly out of the bottom of frame John good to see you buddy so to go back you talked about these people who have uh uh who who you know give you the hand up that sort of thing and then also Maria this relationship that you had with her as as you know almost simultaneously The Changing of the Guard when it came to segment producers one of the things that kellison talked about was um how how you know certain guests would have continually the same segment producer and you would get into that get into that Groove certainly for the end of Late Show uh when you think about you know certain ones for the for for the musical guests or the the political people or or the comedians would have kind of their own their own sort of folks did you inherit like I think um I think Mary Connolly had Chuck Rhoden I think she had Charles as as her guy um you know so so kellison and Mary leave kind of at the same time new segment producer shows up yes you were there as a researcher did you inherit anybody who was sort of used to uh the way things were and then you kind of jumped in or oh God yeah no I mean uh gosh a couple stories come to mind about this um I mean I love Charles Grodin God what he was just a just a just a like a mensch he was just like a lovely human being and he always he was somebody who always tried to um always tried to sort of I don't know he was a very paternal man I remember one time he told me I forget what it was I think he was talking about I think I can talk about this because I think all the people involved are dead but um Bradley Charles including sadly Charles yeah but I remember he was telling me something had made him think about um and Jack Parra is no longer with us as well correct um he was talking about Jack Parr and he was talking about um how somebody he knew a mutual friend of his and Jax had some sort of falling out with Jack Parr and it was very very late in both of their lives and uh and it was over something kind of you know ultimately kind of trivial it was something one of them said that rubbed the other the wrong way or something like that and I just remember and it was fresh in his mind as he was coming in and he was telling me the story he's like I'm just I'm upset about this thing that I heard and he was sharing it with me and he goes you know the thing that people don't think about enough is emotional Capital they need to think about their relationships with people in terms of emotional capital and when you have so much emotional Capital with someone uh store it up in the bank you don't want to throw that away over some thing that that irritates you you know you need to think about that you need to think about all you've invested in that relationship and and he was so he was speaking about it so passionately and I probably haven't even I'm sure I haven't done it justice here but it was actually really moving to hear him talk about it because it was two people he really cared about and I just thought that way of framing it it was such an interesting you know a very just kind of clear clear-cut very pragmatic way of looking at it I thought and so useful anyway uh that just that's wisdom of mine with we know that is that is absolute wisdom but he was a good guy and he was a supporter you know when he you know as things you know as I was a segment producer and then eventually you know when I became an executive producer you know he was he was Cheerleading me you know he was really uh kind about it and and not that we didn't have plenty of kind guests but most people didn't keep an eye on things closely enough to even know that stuff like that was happening nor should they have they didn't need to be but I mean it was just nice he took care in sort of those things he cared about he cared about the show he cared about his appearances he cared about the people he worked with on any level you know um I've got a very well I've got a story that to me it still sends chills up my spine to think about when when when when when Mary did the handoff to me yeah the first week I think if I'm correct the first week that Mary Connolly was not going to be producing a segment was our week of shows in San Francisco that's right this was 1996.

right yeah so it must have been I'm guessing it was sweet so it would have been probably May yeah I'm guessing 1996.

yep so um uh on the Monday of that week uh I'm going to be producing Paul Reiser now actually Mary was leaving the show to go work on mad about you so she was going to be working with polarizer um so she's so you know she had worked with Paul I think a little bit I like just off you know off off books yeah but ahead of time she'd worked with him a little bit yeah but then he was going to be calling me on Monday to do the pre-interview and so I remember her before she left you know the week before or whatever she said uh you know and probably no reason to tell Paul that you haven't been doing this before you know like there's no reason he needs to know that you know just yeah don't leave with I'm new hey nice to see you right exactly exactly I've never done this before Mr you know you know not gonna create a lot of confidence um so um so uh so uh so anyway I'm like oh yeah yeah no that's good advice that's good advice so smash cut two Monday morning in San Francisco 10 a.m local time you know intercom rings on my desk I pick it up they go it's Paul Reiser on your phone I'm like got it pick up the phone hey Paul it's Matt how you doing oh hey Matt big first day huh and I go oh wow so Mary told you and he goes Mary told me what and I go oh he meant big first day in San Francisco yeah yeah so then I don't know I don't even remember how I recovered because at that point it was just like I'd been you know I'd been like hit with a you know a wrecking ball from a crane I was just so so I don't I I probably didn't even recover I probably went like oh it's my first day you know I don't know what I did but anyway it was uh it was not it was not an auspicious beginning to that week which for me was not an auspicious week to begin with either but um but that's a that's a story for another time as they say as Don pointed out uh May 96 uh so that's when you started that's when you crossed over from researcher to segment producer off to a roaring start um and by the way oh before uh before I mean fast on my feet you can see with that quick wittiness why the Letterman show was positive they had picked the right guy for that yeah that's right talk about that pot of coffee right there not necessarily that day uh to the point where you know 20 something years later we're talking about it I love it um and just and and Don did point I was about I was going to say this but he did point it out because he is that damn good um you want to talk about you know we were talking about Charles Grodin and I'm glad we brought him up Dawn on his channel does have the uh the complete Charles Grodin a saga basically right from late night all the way to his last appearance and and this is another good example of of this preparation the segment producing stuff that we were talking about with uh with guests you know some guests would come on thinking oh everything is is spontaneous here I'm going to be spontaneous of course which would be to the Chagrin of I'm certain you and of course Dave we would see it um you know to varying degrees uh as viewers but then you look at somebody where Charles Grodin and Dave had this fictitious tension and this this these two little roles that they would play as as he would be on there for anybody who is new or newish and just kind of doing the Deep dive about David Letterman go to Don giller's Channel and watch Charles grodin's retrospective and I think it's like seven Parts you're in for a you're in for a treat to watch the evolution of of this um Dynamic that the two had um and I mean you know I don't want to beat a dead horse when it comes to the prep for these things but it was clearly you know we've done a good job of talking about how uh you know spontaneity wasn't so spontaneous and it was this Dynamic that was created over time so I just wanted to note that um okay so man 96 you move over you start segment producing that kind of a thing and how long did it take for you to put your hand up and say okay like were you already contributing to top tens and things like that or was it a while before you jumped over to the writer side so uh well a couple thoughts on that so um it was uh so it was I had been having conversations with both uh Rob Burnett who was the head writer at the time and uh Bill shaft who was uh overseeing the monologue and uh um and I remember so I had been you know I had been writing monologue jokes and stuff uh uh and trying to trying to submit um but I remember like asking Rob like can I can I have a conversation with you about some of this stuff and he said oh yeah yeah sure sure so we we we had a conversation and I brought up some he said bring some monologue jokes up to me and bring you know bring some ideas or whatever and he was reading through my list of monologue jokes and of course you know you never get a response from anybody you know you could have the funniest list of jokes there and it'd be nothing or you could have just the worst list of jokes there and it'd be they're not selling anything no no no so um uh so he gets to the list and he goes wow I mean these all seem like Larry Jacobson jokes and I was like oh well that's that's a good thing isn't it and he's like well now because we already have Larry Jacobson he's like he's like you know the thing and the way he explained it to me at the time is that he's like you know um you know what you want you've got if if this is if this is all of Comedy for the radio listeners Matt is extending his hands to the width of the screen uh and uh uh uh radio by the way I'm a thousand years old um uh so uh so anyway no but if this is all the comedy in the world and Dave's comedy is like this uh you know narrower sliver of it then it's right along these edges that the show is looking for writers because they want like somebody who's gonna who's gonna fit into the existing sensibility but also to you know and and it may be not the perfect example because it almost sounds like you're broadening Dave scope but it's not necessarily broadening the scope it's just coming up with some other dimension that someone hasn't quite you know it was the nuances within the narrowed scope right exactly yes some other thing you know um so which I thought was a pretty ingenious way of describing it but it also it also at the time made me go oh that sounds hard um so uh uh and then and then I remember writing some more you know and I wrote more jokes and more jokes and more jokes and I remember taking them up to Bill chef and saying bill will you will you go through these jokes with me and he said sure sure and I remember him going through the list and him going ah well you know the thing about these is they're not really jokes they're musings yeah and I was like oh no I've written musings what and then he and then he picked one out and he goes well this one's this one's more of a joke no this one's a joke okay this one's a joke and then the rest of these music yeah I remember thinking oh it was as if somebody had said I I don't know I guess for me it felt like if I was you know and this is granted a high and mighty comparison but it felt like if I was a Jackson Pollock and I had just done like eight canvases and I'd done them all exactly the same and then someone came in and went okay these seven are crap but that one's a painting and you just go what they're all just I drip paint on all these canvases the same how can one be you know I I had no understanding of like how is one of these a joke and one of these is and if seven of these are musings I had no understanding of it now now eventually now in retrospect I know exactly what he was saying but at the time yeah I had a lot to learn I had a lot to learn but there were learning trees for you to sit under and this is again both those stories are like they're sharpening you the fact that you have these two learning trees that you can go okay it is more than just knowing the voice of the show we want you to find your voice within the voice of the show that can add to the show and create something new which is something I don't think that you ever I certainly wouldn't have ever you know I I I hung out with Steve Young a couple weeks back and and I mean you know we hung out in this apartment for three hours and one of the things you said on your staff favorite moments talking about young is that he would come up with something that just hits you from out of nowhere like completely spontaneous and I I appreciated hearing you say that because he introduced me to two or three pieces of music that he has done that had me on the ground laughing but also and I noted that to him I said it this feels like something that should be on tonight's episode of Late Show like it felt perfect but yeah you know completely that's that's that little margin that you're talking about here it's Steve's voice writing within the show's voice but something that is uniquely his and that's a dimension I don't think we we've certainly never talked about that on this show so so that became your challenge at that point hearing you know chef and Rob kind of give you these extra perspectives now it's trying to figure out yes you know the show's voice you understand that kind of thing but now what are you gonna bring to it that's fresh do I have that right yeah no I think that's that's a hundred percent right and and um uh uh you know I mean I I always think that's the that's an interesting thing when occasionally someone would like this happened very very rarely but it was really interesting to me if like a close friend of mine would watch the show and go did you write that joke because they would feel like there was some some word or some thing that felt like me that had sort of slipped you know slipped through and I always thought wow that is really I mean talk about I mean that is that is squelching out a lot of uh a lot of noise to be able to like identify that that's that's Princess and the Pea stuff you know yeah um so um I always thought that was that was cool I don't know that I'm yeah I mean I think that's a very hard you have to know someone really well and their sensibility to be able to pick out but I guess we would do that on the show you'd go I mean you could go like oh this is a Steve Young Piece you know blindfold me I know this is Steve Young Piece or you know whatever anyway um uh one thing I wanted so so in talking about the transition from single producer to writer I can tell you and this also falls into that category of of um person who made a uh a massive difference in my life in a moment so I would say probably again this here's a here's a challenge for Don Geller so Nathan Lane was on some point in 1996.

I'm gonna say I'm thinking maybe fall of 1996.

I'm gonna guess September um so Nathan Lane uh comes on the show and you know uh I'm I'm assigned his segment and I uh uh have a great time talking with him like he's really fun to talk with and he wants he he definitely like strikes me as someone who wants to be collaborative like he wants to he likes bouncing ideas around and figuring things out and stuff and so I was you know I was really enjoying I was really enjoying it and it was one of the first you know uh uh people that I was working with who kind of sort of engaged me in that way you know because of course I mean it was my first time working with him but at that point it was my first time working with almost everybody that I talked to on the phone at that point so you know nobody had any reason necessarily to trust me or or to engage my creativity or thoughtfulness in that way and uh uh uh and uh so so at any rate I you know I'm pitching things to him and he's like oh that's good oh that's good and then he's like you know any ideas you have write them down and email them to me and you know I like the more the better like just whatever so so I remember writing out this like you know and this is not to say he didn't come with anything he came with he came with stuff but like I wrote just a bunch of stuff a bunch of stuff and and had just so much fun doing it and then sent it off to him but it was kind of like I was kind of I mean I can't ever imagine I can't ever remember sending an email where I was more daunted because it was like wow I just wrote all this stuff and now it went to you know this guy who works in comedy with all these you know big shots and you know what what am I thinking but it was already sent to that point yep and uh he shows up that that evening to do the show and tells me in the dressing room you know we would always meet with the guests uh when they arrived we'd always be there to greet them and then we'd kind of take them through their segment whatever you know sort of um let them in on kind of what we've shown day I mean of course Dave had seen the segment notes but of course we you know there was just that that blue sheet on Dave's desk would just have kind of the bullet points yeah that would sort of lead into an area I mean I always I always thought of it as uh I mean I know Dan kellison referred to it as like a a safety net or something for the thing I always thought of it as being like chords in like a jazz song right it's like it gives you like it gives you some things to hit yep and then hopefully there's you know and you've got a plan for the guest in between there but then the rest of it was was Jazz playing that yeah it is yeah yeah it was comedy comedy Jazz really yeah and and and so you know like 99 point you know uh multiple decimal decimal places out was Dave just either in the moment or something he'd thought of in reading the notes upstairs and bringing to it you know it was very little from us you know occasionally we'd throw an idea for a a quip or response in there but um quip there's a word Dave loves um but uh uh I'm saying facetiously um but but uh uh yeah anyway uh so uh uh Nathan tells me in the dress room he's like I love the stuff you sent and I've memorized I've memorized all of it I was and all of a sudden a part of me I mean of course I was incredibly flattered but the other part of me was like panicked I was like oh my God he's gonna take this stuff that I just rode upstairs and now he's gonna do it on the show in front of Dave I kind of I was like I'm ruined that's really unworthiness I was yeah I was just like I was like oh oh no this is you know uh I I I've just handed him the keys to a car that had the brake lines cut like that's basically like what that's what it felt like to me and uh and so you know I mean as Nathan does like he can go out there and he you know delivers things like it's coming like it's being channeled him like it's coming to you know like it's all like he's just lightning fast and listening yeah and um uh and he's yeah he's unbelievable like that I mean the way he can perform deliver any material is is unbelievable but um so uh uh and also by the way another guy who adds so much to it in the moment so like again I this is not me saying oh you know I on that appearance or any other that I made Nathan Lane funny it's just for the purposes of telling a story it's important that I at least acknowledge that I did write some material that worked with him on the show yes so so so he um he uh finishes this segment he comes up it it he kills with it he just it's he does a fantastic segment and he comes off and he's just like okay that's the best I've ever done on a talk show blah blah thank you so much you're you know on uh just being so gracious about it and so kind and so generous about it so you know I probably can't even focus on any of that because I just think I've just dodged a giant bullet right I that I just think like oh my God so anyway the next how exhilarating that is by the way like like you're looking back and thinking about that how exhilarating is that I get moments of that right now I get moments of that when you when you return an email to me like I get moments of the I seriously and I mean I'm I'm I'm dead serious when I say that like that exhilaration that you're talking about I love hearing that and there is no I don't know if you call that a high or what you want to call that high wire act anyway I don't know what you want to call that but there is no feeling like that and I love that you can kind of go back to that feeling and kind of refill it again because at the end of the day it's growth but it's fun but it's also set professional satisfaction and all these things I love the joy that you're taking telling this Matt oh yeah yeah no well because so then yeah the part two is even more surreal so then the next day I get a phone or I get you know my intercom boxes uh yeah Nathan Lane on your phone oh my God I'm like here we go yeah so I'm like well this first thought is well this is strange a guest never calls me when they're not calling me for a pre-interview right and then second thought is oh my God he's realized that he's been had he did all my material on television and he's realized that like there was some fluke and the audience here laughed but it was really not good here comes the brow beating right exactly exactly and um uh so um um I pick up the phone and Nathan says Matt I um so here's the thing I'm doing a Friars Club event next week and I'd like you to write material for me and I said to him uh Nathan I can't do that I'm not a writer uh but I can put you in touch with like one of the writers upstairs and they'd probably be happy to help you and there's this pause and he goes is this Matt Roberts and I guess yes and he goes the same Matt Roberts that wrote all the funny stuff that I did on my segment last night that was the best appearance I've ever had on a talk show like he literally said all that and I said um uh uh yeah yeah sure and he goes okay well look here's how it's gonna work you can call it whatever you want but you're gonna do what you did yesterday and I'm gonna pay you money that's what he did he hired me I wrote I wrote a bunch of jokes sent them off to him he invited me to come to the event with him to write you know what they call ad-libs uh uh uh off stage uh for him at the event and uh and uh you know that was like that was that was really the first time anyone ever said to me you're a writer and then Nathan and this was all with the show's blessings but Nathan uh then hired me to write uh for the Tony Awards uh uh and then a second Tony Awards um and it was the second time writing for the Tony Awards that I was actually inducted into the writer's Guild based on that so I became a writer uh actually outside of the Lettermen show while working on the Letterman show and then it was it was sort of in the wake of that I mean that was probably like I don't know 90 I I don't know the years when he hosted the Tonys but it was probably 97 98 somewhere in there 99 I don't know something like that but it was in the wake of that that that it it became sort of apparent to the powers that be at the show that I was I was writing tons of material for guests I mean between you know Marty numbers and and Nathan stuff and yeah a whole bunch of a whole host of other people it was just it was a I was doing I had made the job almost a writer's job you know uh uh for like I said because that was what I felt like my strength was you know and uh uh uh uh uh and then again this is all you know I would say I would say the same for Maria Pope as well uh doing it you know in concert with her um uh but uh so but that was really where it all began and then that was where you know it it you know they offered me the the writer's Credit in addition to uh producer credit at that point because I had also then started taking on sort of you know sitting in on bigger meetings and and getting my uh thoughts on on other things and bigger things so that was sort of that was it was it was a most unconventional path to becoming a writer because really what it was was I was I was a writer but I was primarily writing for the talent I was still submitting to the top 10 list every day and trying to get monologue jokes in as well but I wasn't able because I was producing guest segments I wasn't able I missed out on getting to be at the writer's meeting in the morning or to sort of you know uh assemble with the writers in the afternoon or you know I so I didn't get I didn't get to kind of participate in a lot of the culture uh but um but you know I did I I had the whole other Advantage which was getting to collaborate with all of these uh unbelievable hilarious talents that came on the show so it was uh it was a it was a great Niche to have um that story uh is easily easily in my top 10 if not my top five stories uh that I've heard on this show uh that is the that is absolutely fantastic um God I just I I love that so so much it's just a such a beautiful uh part of your career blossoming and what a way to make it happen you know to other people discover that you're a writer before you discovered even though it is kind of the desire that you had at the beginning to be told you are this you have arrived and to get there through that weird side servant door you know into the writer's Guild before you did it for Letterman that is really really cool um you just by that point what you just described at the end of that story I mean it's safe to say that you know talk about life balance and all that kind of stuff the scale is tipped down at the very bottom everything is the show at this point I assume I mean if you're if you're collaborating on all of these things you're the segment guy but you're also in some of the higher level meetings showing without even trying to say I'm ambitious you're just excited and wanting to be part of it all that show at this point was your life correct oh yeah yeah 100 yeah yeah without a doubt I mean I would say the show was my life I mean the was my life going back to I mean really really almost from the beginning to be quite honest with you I mean because even as even working in the ticket office it was nine hours a day in the ticket office five days a week but I mean I think I mean I don't I don't remember what I was paid at that point but I mean it was not it was not a uh it was not a substantial sum of money I mean I think I don't know that I was even making uh you know 10 bucks an hour at that point or something you know I mean the retail retail jobs were paying about 750.

so I'm not sure that I was making 10.

so if you think 45 hours in a week ten dollars an hour that's 450 a week in New York City yeah I was living in a studio apartment at the time that was a dump and I was paying no this was before this was this was this was the place I lived in before I moved into a place where we got robbed but no 675 a month in Hell's Kitchen before again before Hell's Kitchen was cool um uh and uh so you know 450 times whatever four and a half you're looking at I mean maybe I was bringing in two thousand dollars a month which after taxes and after 675 rent and after I don't know 300 in student loan bills were like it was like there was nothing there was nothing so I had a second job um working in Trump Tower at the Abercrombie and Fitch store on the second level of Trump Tower and I would go there at night based on all my retail experience and for like seven dollars an hour or something like that I would help them uh like fold yeah like fix up the store for the next day so it was you know folding vacuuming you know yeah all the stuff yeah all that stuff so I would do that and then on weekends I'd go in and work like a full full shift Saturday and Sunday during the day on the sales floor like you know um uh because I pretty much looked exactly like an Abercrombie and Fitch Guy totally you know no this is this is very telling you know the reason they hired me was because this was back in the day when it was when Abercrombie and Fitch was um the look was like eight layers so it didn't matter if it was the dead of Summer it was it was T-shirt with a henley with a dress shirt with a flannel a shoulder came down to about here um and uh you know uh so so yeah no I had the build for that kind of Abercrombie and Fitch not the new Abercrombie and Fitch where it's like you know cut off the shorts even further and put on a tank top and stand out in front of our store uh now so uh that so yeah I was back in the day of a more chaste Abercrombie and fish I was working there but all this Finance your Letterman habit this is all to say that like yeah this was because I wanted to be a letterman so that was weekends that was weekdays research was the job where we'd come in at nine in the morning to be ready to give stuff to the not eight or nine in the morning to be ready to give stuff to segment producers and we would leave oftentimes at 10 or 11 at night um sometimes you know sometimes a gaster drop out and you'd start your research at 10 at night um you know uh so uh no so I mean I felt like you know uh and then being a new segment a young new segment producer I just felt like I needed to put everything into uh into it uh yeah so so no I mean I felt you know the the Letterman show really it really was uh it really was it really was my life for for most of that time that's not to say no I I didn't have some great experiences and and make some good friends outside of it but it was really the the bulk of my existence yeah well and it was your heart's desire and your and you're and you're working your butt off uh you know earnestly for for that and then I just love hearing you know the how it paid off and the results that you got from it um you know okay so talking about writing here I gotta ask do you other than a segment uh where you're collaborating with a guest and you're so honoring and I appreciate that I think it's okay that you say if you gave somebody a great line that played really really well I understand how you want to keep that okay fine let's go back to you yourself uh first thing you oh go ahead I just thought of one okay I just thought of one I just thought of one and I think it's okay because it's it's in line I gave Nathan Lane okay and and I gave Nathan this line and since I've already acknowledged how funny Nathan is and how he writes like so much of his own stuff I don't feel bad doing it yeah um but it was also funny because there was a there's a Dave coded to it so the joke was that Twilight the sequel to Twilight it had just come out it was called Twilight eclipse yep and so the line I gave Nathan I think maybe we might have even Don might remember this but but the the the the line I gave Nathan or or I'm sorry I think we had Nathan I think we inserted him maybe into a clip like a fake clip of from Twilight eclipse and um but but in the setup to that he said yes I'm in the new movie Twilight eclipse it's called Twilight eclipse because you shouldn't look at it directly and uh uh I'm Shameless about laughing at my own line I'm sorry good no please I'm thinking about Nathan I'm thinking about I'm just thinking about Nathan delivering it and thinking well that's the thing it's somebody else and delivering it in their own Cadence in their own yeah and and Dave reacting to it and um um so then the commercial break comes and and as I walk up to the desk Dave leaves I hear Dave lean over to Nathan go okay that joke Twilight eclipse don't look at that that is a great joke and Nathan goes well he wrote it and then Dave goes Dave goes looks at me and goes would it kill you to ride a line like that for me once in a while yes yes he's like you're here every day you could just once in a while write a joke uh oh how did that like I mean okay like that just the kid who wanted to be part of the club and then you have that experience there like that is you're in heaven you're Invincible at that point like that's that it doesn't matter no no no no that stuff matters when that moment happens and that appreciation from that man comes to you that way uh what a what a lovely lovely moment that is I'm not built in a way that I've ever for even a moment of my life felt Invincible but I understand what you're saying I didn't think there was an hour of the of my experience at Letterman where I ever felt Invincible but but uh you know uh that is a beautiful beautiful sentiment by the way Don's having some technical problems on his side of things he's already let me know that but uh um but yeah he'll he'll be able to if he is still watching I'm not sure he is but at some point he will come back with the the date time and minute that that joke was set um the uh I had something with that and then it just went away talking about why Don's not here crap where did it go it was right there it doesn't okay this is just for the record this is the second time Don has interrupted the uh I remember I remember where it was now thank you thank you for that that you covered beautifully for me there uh it's like you've produced somebody before um okay first thing that you got on the air that was yours that Dave said then like what would do you remember or the first notable where it's like okay I got this on uh well the first thing that he ever I mean the first joke I don't remember the first jokes that I got on because then it would have been intros no it would have been intros for the um it would have been a joke in an intro for a guest oh that makes sense okay yeah so like you know we would put a joke in the intro sometimes and if it got you know if if it got used I I mean the first time that ever happened I'm sure I was beside myself the first monologue joke God it's an embarrassing it's such an embarrassing line and then and then like all of these things where you go back and you look at jokes we made and you go like you know you really have to this is where at the bottom of the screen you know instead of writer's embellishment it needs to be flashing it was a different time people it was a joke yes I think we all assume with a 32-year run yes in a late night broadcast we've seen different eras when it comes to taste and political correctness and all that I think we're all adults here we can understand that um and anybody who goes to try and take the past and and and and uh use that in today's context to attack or to do anything nefarious at all uh that's cheap and no I think we're all adults here we all think about that so well I get that yeah I mean it's you know whatever it's just one of these things where you go different time people yes but um uh so we were raised on porkies everybody Gen X guys and genetics we were raised on porkies just so you know okay anyway continue on this will make it all very clear though it was a Bill Clinton joke so um so but it was I think it must have been after let me see no no as Bill Clinton was in the white house because the joke was it was a it was on Halloween so that makes it that reduces it to uh a span of only uh 23 years that Don would have to go through to find it um no and it was it was early on um and it was during the clean years Clinton in the white house it's down to like two years um anyway uh the joke was uh uh um oh right about now uh down in Washington DC uh Bill Clinton is helping an intern out of her costume um and uh uh so there you go and uh um uh and that was the first joke I ever got on the show helping an intern out of her costume and Dave just enjoyed I remember him sort of maybe hoping is the key word there yeah but yeah what Dave found funny about it was I think just that it it sounded it sounded like uh wrongly gentlemanly let me just help let me help you help you out of your costume that's what he liked about it so um so anyway that's what the uh that was my first joke which you know I say uh both with the fond memory of how excited I was that it got on the show and now our retrospective shame but oh gosh no I yeah I I don't get me wrong I love where our culture is now how we are reflecting and saying how can we improve uh but the the pendulum has swung way far um you know when you take things uh going all the way back on to Shakespeare I heard someone saying it about Shakespeare the other day God it was hundreds of years ago okay it was a different time different place never mind the um Breakneck speed of things that we have seen and the changes that we have seen in our lifetime like I mean let's give everyone a break everybody especially when it comes to Comedy I will say I see both sides of it because the other thing I'll say is that um you know uh uh so as somebody like you know I didn't come out as a gay man until I was like in my mid-20s right and part of that was part of it was my own stuff going on but there was definitely a part of it that I think I was concerned about that from the standpoint of could I really could I be has there been a gay writer at Letterman and like it's kind of a fraternity kind of a boys club uh you know would this be accepted Am I by coming out is this going to ruin any chance of you know would Dave ever have a writer on the show would he be worried about somebody writing a joke that would potentially could make him seem gay like you know all of these things went through my head and to be quite honest with you I even had the same even though clearly that wasn't the case right I had the same fears again about as a writer ever thinking I could become a head writer because I thought well I don't know if Dave would be comfortable having a gay head writer so I I and you know and some of this comes from you know uh you know you look at jokes that were done on the show that that you know by the end of the show's run Dave would say oh no we're not doing that joke but you know there was a show about your you know there was the joke about the gay pride parade going down uh Sixth Avenue and you could tell it had gone by because the windows had been redecorated you know uh uh you know uh so all of those kinds of jokes right and I mean you know I laughed along with them but you also do you know I so I can I can I can hear both sides of the argument you know on the one hand you say like come on people they're jokes but on the other hand it does create potentially it can't create a situation where somebody goes like well it is it a joke or is it am I a separate class of person yeah and so the nice thing that I would say is that you know what I learned there over over time and uh uh and through my own experience I should say um was that you know it it didn't matter to you know it didn't matter to Dave and and and uh uh uh you know it was it was a it was a the place was really embracing in that regard but I guess you know that sorry I know it's a weird detour but I do feel like you know I do feel like it gave me a perspective on that where you can kind of go like yeah it is important I I can see I can see how it's easy for someone in a place to go like come on it's a joke on the other hand if you're on the other side of things you can kind of go like yeah I know they're just kidding and I know they're not bad people but maybe maybe it means I'm not part of the club you know so that that's those are the those are the two sides of it I think well these are okay and it's and it's points like that and discussions like this that move the conversation in a productive positive way it's when the you know the finger pointing and the and the lamb based thing and the molotov cocktails of things in the past that don't it doesn't help but what you just said and obviously you know coming from a a writer at the highest level of course articulate but that's where we need to go like the back and forth of things where empathy shows up on both sides and you're looking at things but you know again talking about that being a Gen X kid raised by porkies and having to figure out uh how to negotiate your way through that that's out there and the club that you wanted to be a part of even more gratifying at the end knowing oh wait a second yeah yeah I am a part of things here that is a beautiful sentiment as well this is the episode Matt that has so many beautiful sentiments in it I I it's so lovely is this going to be a very special episode of the Mike Chisholm podcast of the Letterman podcast uh Letterman podcast I know but I was going to put your name in it just because I thought that you know I I it already is um it already has been uh but yeah no I mean I love that you went down that path I'm so glad that you were able to talk about that because it is a big deal it is a big deal when you talk about like so I gotta ask you this question head writer the last head writer for David Letterman and and had this this shining career of course with ups and downs and all that stuff we all know that but at the end of the day with reflection so much joy and so much um you know excitement for it still you can put yourself back in these exciting moments um are you I shouldn't say just Matt Roberts I'm not meaning to say it like that um but do you look at that as saying okay I'm grateful that I can be an example for some who might consider themselves a minority or disenfranchised or or think that they have less opportunity is there a part of you for lack of a better term that has some some pride for that part of of of your journey oh sure I mean sure if it if it if it matters to anyone uh in that way that would be great I mean I don't I don't I mean I I guess I don't necessarily think of it in a I don't know that that's something that many that any people would have reason to know about me or or even sort of see it that way and you know view yourself as a trailblazer no it's not usually one of the first uh thousand words that come to mind when I think about myself but but um uh the uh no but I would say you know I mean I have tried you know again to refer back to my college I know I've given my call it sounds like I'm just it sounds like I'm paid by Bowden College to give them plugs I just love my I love my college and I love I love uh uh I I to this day I love the their mission and I have so many so many of my closest friends are are uh connections through that that place so it's it's really near and dear to me um uh you know my life can be boiled down to almost three like families and that's the one I was born into the the the the Bowdoin College family and the Letterman family I mean that's like you know I've been uh had the Good Fortune of those three uh three things um but um uh uh but uh at Bowden you know I do I've done a ton of volunteering there and stuff like that and so you know I think because of the sort of profile of my uh job and career and whatever you know I've been someone who um they've asked back to talk to students about things and I I I I do like uh participating in like any of the lgbtq uh plus uh kind of events conversations that are there when I'm back on campus or whatever because I do feel like it's important for people to see uh uh people not only who went off and did all manner of different things in different places but also to hear from people who who had uh doubts or maybe took a long time to come out or um any of those things just you know just hearing people's stories is always uh a comfort I think to for any part of you where there's anxiety or doubt or whatever so yeah so maybe in that way in that way but but you know from from uh from another from the other standpoint from like a sort of history of the show standpoint I'm not sure that it's uh um uh you know I'm not sure that it's uh I'm not sure that anybody has ever even thought about it other than me um well and I mean you've done a fantastic job once again of showing the uh the minimizing and the self-deprec it's not quite self-deprecation but the the minimizing of of roles I think uh the example uh is is is is incredible for all sorts of aspects this being one of them um but I just appreciate where you're coming from and how you're you're able to talk about that today and shine a light on that for shows like I mean and not just I don't want to just put Late Show as as uh an example of this but a lot of these comedy shows have been you know given especially in the writers rooms you know talking about the lack of inclusion and things like that and and whenever you see somebody who breaks that and starts to create new patterns um it's always it's always a few people that kind of start bumping on the glass before it breaks through and you realize okay the ceiling's now gone um and that is very very cool you are a part of that and I just appreciate that another aspect that I appreciate about so again though I would say this isn't I mean I'm I'm truly not being sort of self-deprecating or minimizing it here I think I think it was I I don't think there was I think I worried that there was a ceiling there I don't think there was a ceiling there so I just wanted oh I see okay I'm glad you made that idea yeah no no no I I I yeah I'm sorry if it came off that way but I was not suggesting that there was I was suggesting that I perceived that there might be would I be able to I got you would I be accepted if I came out would you know uh uh all of that stuff so it was and there was nothing never ever any resistance at all there was nothing but but but that was again that was my point was that you know even if there isn't a ceiling when there's language or jokes or whatever else that might make someone feel like there could be a ceiling then then the difference between there being a ceiling or not being a ceiling sometimes is irrelevant right so so so what I'm saying is you know uh it's it well it's not a pat on my back for breaking the ceiling or anything else you know there there wasn't necessarily a lot of uh there wasn't really a lot of Courage I was actually just to a point where I was like I'm gonna go out of my mind if I don't just start acknowledging a part of myself and and so I think it was at that point it was like well hopefully it won't be the end of my uh career but if it is then I just have to deal with that again this is all stuff that's going on my head this is something that's not necessarily a result of the show but I'm just saying that like the the way the show the types of jokes that might have been existent everywhere in our culture when the show went on the air versus the kind of jokes that we wouldn't feel comfortable making by the show that went off the air is probably that's probably forward movement for someone like me coming up now versus someone like me coming up when I did that there would be less of a reason to think that there might be a ceiling there even though you know even though there isn't um and I think that's largely the way you know I think that's you know I I don't know I'm speaking outside my area of expertise but I think you know again it doesn't matter if there are you know 100 out of 100 places have ceilings or 10 out of 100 places have ceilings if it's a perceived ceiling that's the only thing that matters so I think you know I think that's why when I said I saw both sides of it that's what I'm saying I can see why somebody could say there's no ceiling right and you know what do you care they're jokes there's no ceiling and it's like right but it you know it's it's this it's the sense of it it's the sense of that otherness so yeah anyway it's it it certainly has created that's a whole other discussion it's created a lot of problems for comedy that I'm also I will also gladly acknowledge that like you know to get this conversation in simple ways is impossible because and everything ultimately at any point in time is a judgment call and you know I mean that's good Lord that's how we that's how we spent so much of our day you know so much of our day every day because you're coming up with new material and the last thing you want to do is put on something that's you know offensive or but yet you also want to be funny and fresh and smart so you know there was no shortage of conversations where we go can we make this joke does it or or a joke would be thrown out because you'd go like well no I think that could be perceived this way and even though that's not what we mean get rid of it you know I this is why we do long form and I mean we're doing you know because I won't shut up I pray to God you edit this if if Mike doesn't edit this listeners at home if Mike doesn't edit this I apologize um laughs no I don't want to see comments I don't want to say comments in YouTube that say this should have been edited because I'm telling if if it's not edited it's not my fault okay Mike unknowingly lifts up a softball for you to just crap that was hilarious oh God no that's not what I um um this is like I love this conversation so much and I'm so you you are so you're so well articulated and I just appreciate that so so so much I just uh yeah thank you very very much for talking about this part of it and and um so that being said the Clinton joke you know going back to what started this here um you talk about that and then producing uh President Clinton when he comes on the show like okay not only were you a part of a show uh you know calling him Bubba the whole nine yards like all of those jokes along the way during his presidency but then he comes on the show and and you know everybody no words of Bubba no no you know like the best behavior best all of that stuff right and then on your staff favorite moments you know that him him making the joke that has the word blow in it uh I think right there that kind of shows that all of us no matter where we are and what what's happening there uh we can walk into comedy we can walk in and we can look back at these things and laugh but the Clinton thing I want to talk about for a second you actually first thing you got on the air was a was it was a nice little Clinton joke and it is it's a nice little Clinton joke that's a great thing to get on the air for the time all of that thing all the things being said um when he came on the show that time uh was everybody on their best behavior did he ever go back and say oh yeah you guys you know you guys used to take some good shots like I know I've heard Bill talk about or President Clinton I should say talk about these things in the past where people would take shots at him you know all that kind of stuff and and he's pretty good natured about it did it come up at all or was it unspoken for everybody the whole time uh I don't recall I mean I have to say my recollection of of Clinton being there I mean and and and really with most presidents who've done the show the time you have with them is so uh brief because they're constantly doing things it doesn't matter it's not like they just it's not like they've got an hour and a half set aside to just do Letterman like there's three more things after this there's well but also yeah and people are showing him other things for stuff yeah later that night or can we send this thing out can we put this thing out you know here's you know there's probably 10 things going on in the world that he's being briefed on every half hour about you know things these situations he's following domestically internationally wherever else um politically who knows you know um so so you know you would get maybe five minutes with them and and you primarily want to try to go through the bullet points of the segment to like yeah you know make sure that they're okay with things make sure that if they told you a story if you got a pre-interview if they told you a story uh you know you want to tell them sort of how Dave might lead into it um and uh so yeah I mean it was very uh very rare that uh so I don't think to answer your question I don't think uh I don't think uh President Clinton volunteered anything he said about it would have probably been on the show and I'm sure Dave acknowledged it that first time he must have said we've given you a hard time and I give you a lot of credit for coming here or whatever right um yeah Dave always did I mean he always respected uh uh people who you know who would do the show despite all the jokes and everything else so oh those were the best guests though the ones who got it and and and had the uh the hutzpah whatever you want to call it to actually come on and and um and do it you know I met um I met Governor Palin um a while back and and I got her to like I got the picture here somewhere shecky made me take it off the set I had it on the set he made me actually take it off the set but I actually have an autographed picture of Sarah Palin uh to the Letterman podcast good luck with this and she underlined this uh three times and when she read it out loud it was to the Lettermen podcast good luck with this um jokingly of course and I you know in talking to her as as she did that as we kind of went back um I sensed and hopefully one day I can actually kind of get her on here and we can talk about it but uh I sensed I sense regret that she didn't come on the show um I I think that would have been a perfect example like like when her running it when Senator McCain came on the show after everything uh you know that was fantastic you know I screwed up and and and then Dave you know they they go back and forth and back forth and then All Is Forgiven everything is fine it's all good um you know well yeah there's there's every example of that and then also I I you know I mean uh you know uh you know this is this is inherently sexist but I mean in a uh uh uh you know Davis Dave is is an old-fashioned Midwest guy the last thing he's going to want to do is to look like he's beating up on a woman in the guest chair so she also had that going for it if she absolutely after all of the you know uh uh after all of the you know jokes that she he made at her expense and everything else I mean the last thing he was gonna do was look unchivalrous on top of everything else so forget about the credit you know forget about what might be applied to Donald Rumsfeld when he does the show you still kind of go like yeah but Dave would still take a swing he's the he's a secretary of defense if he can't take a punch who can you know but like and actually again Dave was unbelievably generous to uh Donald Rumsfeld but um uh you know I just think like that's another calculation that you just kind of go like yeah I wouldn't have had if I were advising Sarah Palin I would have said you are going to be fine on that like yeah you know and by the way you can call him on everything he did and he's just gonna have to sit there and take it because he's not gonna he's gonna have nothing to say so you're gonna look like you're gonna come out as the as the hero in that uh in that situation so exactly and and you know see the see the Oprah Winfrey segment and and um this is something okay Don's back his technical uh problems are are gone here and so I'm just gonna keep going he's going to pop on here I don't know if he if we see him or not but you were there this is another cool part and ended up being the head writer at the end to tie things up at the end we'll get to head writer in a second my God uh and I think we will actually get to it which is amazing to me considering all the things that you've done for the show Matt um but uh I think about some of the bookends that you got to see hey there he's back oh he's gone um okay I think he's still in the background you got to see the bookend to the Oprah Winfrey's thing you know maybe you weren't there when he when he when he when he offended her unknowingly or knowingly whatever in Chicago uh back in the day and then and then you know but you were there for the over log you were there for the whole thing and then you got to see some of these payoffs that happened you you didn't uh you were a part of producing her when she came back on you would have been head writer by that point already right or pretty close yeah no I think uh I think that might have been and come uh well I don't want to say for sure I'm sure Maria was heavily involved I think it was okay yeah yeah but yeah you get to see these bookends from Letterman lore along the way you know the last Darlene Love the uh you know Oprah and Dave making up all of these sorts of things um we haven't talked at all about the part of you that all you wanted to do was work at Letterman to be in the club to be part of that we haven't talked about that part of you having these kind of holy moments like you stayed a fan the whole time you're still a fan now like we you know um some of these moments where you're saying it as a letterman fan rather than a than a than a writer or a producer um you know did that still exist or were you just so in the hurricane that you couldn't be that guy you couldn't really be that person at the show doing the show I mean it just wasn't like first of all it wasn't really part of the culture like it was part like you know it was uh it was kind of it was kind of it was kind of uncool to think you were cool it was uncool to think you know it was like um you know there was a a sort of humility that was encouraged about you know that that was kind of you know a top-down a top-down since again another part of Dave's sensibility was you know I mean what I loved about him in 1982 what did I started watching him was about how he would take the air out of you know uh blow Hardy celebrities right and so you know I think the thing was you know there was uh not only did Dave not want to be a blowhardy celebrity he didn't want blowhardy uh producers or blowhardy writers or blow Hardy anybody so you know I think I think we were all very um careful about that even even to the point where you know I remember like you know we'd all get cast in bits as staffers and whatever we'd be extras on the show in various ways or some people got to be characters obviously and but you know the last thing you wanted to do was to seem at was to reveal at all that you were excited about that like it was not you know humility is the rule of the day so the last thing you know you would never you would never want to reveal it would just you know it's got to be a little show I'm gonna yeah I'm in a piece on the today you know uh God damn it yeah no in a way you know it's funny reflecting on that because I was thinking about a lot and and your enthusiasm watching your your podcasts or you know on YouTube and stuff you know it's it is infectious and it's it's a I love the spirit in which you do the show um uh but you know there is a part of me so much of that I think was sort of suppressed for so long yeah that there is there's a part of me now as I kind of reminisce and look back and now and now also it's been you know some distance now there's eight years since the last show eight eight years in a few weeks since the last show and um uh you know there's almost a part of me that uh goes did I really work on that show because that was my dream I you know and I was there 23 years about given with the internship included um yeah there's still a part of me that like you know and and at uh Rick sheckman's Memorial you know seeing all these people again who many of whom I haven't sadly haven't gotten to see because I've been living in different places and whatever else um I haven't gotten to see you know since a couple people I haven't seen since the show ended a couple you know a couple people it's been several years uh many many people have been since the show ended and and uh you know I love these people I really just deeply love these people um and uh and yet and yet it feels like another lifetime yeah like and and so uh you know so remembering uh uh uh uh remembering these things and thinking about it all you know I think Paul Shaffer refers to it when he talks to you it's like there's so many things sometimes somebody will mention something you'll go oh yeah I remember that I never would have you could have you could have you know put me in a polygraph for a thousand years and I never would have been able to reveal that story and then yet somebody mentions something and you go oh yeah that that did happen that was funny and then you're right back there but uh yeah it's uh no it was a uh it was a uh it it was like a a non-stu it was a Non-Stop uh ride yeah pretty much from the beginning to the end because in all honesty whenever you got a week off the last thing you wanted to do was reflect on the show so so pretty much like the week off would come and you'd be like I'm gonna try to forget about the show until two days before I get back because then I'll start having the uh the stress dreams and the and the what am I going to do on Monday and what are we going to do for the you know but um uh but you know so it was like a you know it was it was either full-on or just like let me forget that this is happening at all for like five days just to clear my head yes and then I'll be back in it you know uh you actually took a you took a question off your do you still dream about the show that was actually a question that I had for you not really I don't think so I mean every once in a while there'll be like a random uh the the nightmare the the show nightmare the Regular Show nightmare was usually uh because I think I did it for so long was segment producer based and it was just that um uh we would turn it in the notes today but three o'clock on a typical show day and uh it was just that it was three o'clock and uh and I hadn't started my notes like that the notes were due and I hadn't started the notes and so the crazy thing is that actually happened once because uh because you know at one point we were taping two shows a day yeah or no at one point now what was it it wasn't because of a two-show day it was because of something where like I think I I don't remember how it happened but maybe a guest got swapped around from one day to the other there was a move or something and I and then maybe someone else got moved so it got switched back or something something where it was like I didn't know I didn't remember the second part of it and it just got stuck in my head that oh this is Switched and so I get a call down from Dave's assistant and she goes yeah do you have the notes for uh and I don't even remember the guest was do you have the notes for so-and-so and it was this moment of like oh no oh oh oh no I had done the pre-interview so I had I had done interview but I thought I was going to put the notes together for him the next day I think what it was is um one of these things where I had done two pre-interviews yeah and and I had switched the days in which the guests were coming on so I had spent all day working up notes for the wrong guest and then and then at three o'clock found out that oh no I need these other guests and so I just said I I said it was Lori Diamond I said uh oh my God Lori I did the wrong notes I'll have notes up to Dave in 20 minutes yeah and she's like okay no problem don't worry about it I'll tell Dave and I never heard another thing about it I mean it was um you know it was uh uh mistakes mistakes happen you know I remember I I um just a another story along those lines uh I just remember very early on being a segment producer and how I felt so responsible for everything I mean technically you are but everything that happened during August segment if something went badly and I just I I would just it would eat me up and I remember one night a segment really did not go well I forget why but I just remember going up to Dave's office and I just said I I just I just want to apologize today I I you know I wish that segment had gone better and I'll work harder or something like that and Dave was in the office his office next door and I think he heard me saying that to Lori and he uh came out and he said uh um I I mean I just remember him being very gracious about it just saying you know uh you know it happens this is a this is an art not a science and um you know there you know you do the dude you do the best you can and you try to make it work and sometimes it's just not going to work and uh and then there's always tomorrow's show or something like that and it was just like I just remember I mean I still felt bad about what the the segment but I felt like it was uh it was an acknowledgment and it was a rare because the the the standards we all held ourselves to and the standard Dave set for the show was very very high and um uh and so you know there wasn't a lot of talk like that it wasn't like we were going around every day going like this is another show tomorrow like that wasn't yeah that wasn't ever the attitude no but I think I think because Dave saw how much it was how much it was bothering me I think you know I think in that moment I think he realized like that was that was the time to sort of yeah uh administer a little bit of uh of uh Grace for lack of a better term you know well and empathy and and yeah hurricane for a second yeah yeah yeah oh that's uh okay I've got two or three more do you have another do you have another few minutes for me here sure you do okay yeah I don't wanna I don't wanna you've been so gracious with your time speaking of Grace um I appreciate that so much I do want to talk uh the distinction between okay there's three things I want to talk about okay and I'll and then and then if Don wants to throw something in there whatever um but there's three things I want to talk about still uh and this first time having you on this has been a very special episode no if it's been great I love this so much man like I'm so excited about this um but there are I want to talk really quick about if possible the distinction between the head writer and and being a writer and being the head writer and kind of what some of those jobs are and I've meant to I've had a couple head writers on here and I've wanted to ask that question but I haven't done it yet and people have kind of criticized me for it um that's one of the things I want to ask so what's the difference between a head writer I want to ask about what you've done since the show like you're in London now and talking about this some of the award shows you worked on and things that you've done uh I want to talk about that and then for me personally I want to ask because it's one of my favorite bits of all time you did talk about it during the staff favorite moments which I am so grateful for the hypnosis thing to me as a fan sitting there trying to pick my brain up and put it back in my head as a viewer I can remember watching it I know exactly where I was we recorded it we watched it multiple times that's the other thing I want to ask you about that one's just for me but the idea of the the head writer um as opposed to being a writer or being the monologue writer or whatever the head writer what other duties did you have as the head writer that were specifically very different from just writing content for the show yeah well I mean the so the um to me and I suppose every head writer can operate differently but I mean at the Crux of a head writer job as a management job right it's a management job it's an editorial job so the irony to me about the head writer position is I always thought and in many cases you know the star writer at the show like particularly early on the star Riders were the head writers right right um he had Merrill Marco you had Steve O'Donnell right um I mean that's a power Duo uh right there back to back um but you you also like you know I from a strategy perspective that means you're going to be there like on the one hand it means they are editor-in-chief for the comedy right so you want the person and quite frankly you also it's a um it's an endless uh just stream of Comedy that's being put out by all these really unbelievably talented funny people on the uh on the 14th floor and yet it's also coming so fast that like you might have you know you're in this position this sort of uh I mean it's a it's a diff it's a it's a difficult position because you want to respect each writer's work and and their diction and their you know everything that makes a writer a writer but at the same time you might get a script from them at 10 55 a.m and it needs to go into production in the next five minutes and calling them up and saying hey here's uh I'm wondering what do you think about shortening it by losing this paragraph or changing this word or whatever there's no time to do that and if you know part of the job is knowing uh is is trying to sort of second-guess Dave and to think like oh Dave lately he's been saying he wants things a little shorter a little tighter he didn't like this angle in in some jokes that he cut last week like last minute Joe he didn't like that sort of attitude so I'm gonna twist the attitude on the end of this joke to be something that he's kind of been going for more lately and I know that like you know I know that it's a it's a thing that like uh it's a thing I kind of hated most about the job because you know yeah you know it's it's it's altering someone else's work but it's also kind of what is required because you're just your job is to you know get dishes out of the kitchen and onto the plate and Dave to approve them right and so what a stifle creativity but you do need to streamline the creativity exactly and you if he's been saying like oh they think something coming out with a little bit too much black pepper but I'd like a little more salt then you're just like okay I don't I I know you love the you think this dish is perfection but we're we're changing the seasoning so uh it was a lot of that um and it's it's so it's editing it's uh planning it's organization it's managing the department it's you know it's all the stuff that a manager does you know it's it's uh it's you know talking to people when they've got issues that are affecting their work or uh you know uh hrl issues to it as well yeah all that sort of stuff yeah all that sort of stuff um but it is ironic that it's like you know I think if you would ask me you know as a kid what the head writer what position was I just say oh that's just the funniest person on the show and I mean I can tell you having been the head writer that I am I was far away from the funniest person on the show um I I just uh I think I think they made me head writer because they felt like I had a good uh a good balance a good balance of understanding what Dave wanted I was I had spent a lot of time facing Dave um I had spent at that point I I was sitting in the writer's meetings every day from the time I became executive producer um so I was participating you know in them at that point um going forward so that was uh that had been almost five years I guess or or yeah something like that at that point uh yeah so I think it was just that it was they you know they saw me as as being uh uh qualified for in that way but you know I don't know if it's a good I and again I don't even know if it's a good like looking back I kind of go like gosh would Meryl have been able to come up with even more great ideas if she hadn't been the head writer or would things that became signatures of the show not have gotten selected by a different head writer you know it's one of those things where you go who knows it's a it's a whole uh it's a whole uh a whole question but I guess uh um I hope that answers wait sorry my God Beyond yeah no no thank you for that I appreciate it so much and and I mean I'm certain in the future we can go in and have uh you know similar musings and and whatnot show ends in 2015 priors Club you know the event at the Friars Club it's all done um you know what next you know the the culture shock of doing this from your formative for all of your formative years but still clearly have learned so much so much in the tank uh but you just don't know where the tank now attaches itself to uh what have you done what have you done since then and um what are you finding passion in these days other than living in London and I love that you I'll I'll tell a little tale out of school because I think it's okay you always dreamed of living in London and and you live there now and you're scratching that itch which is lovely uh are you enjoying your time in England and and uh and what are you doing spending your time these days Matt yeah um uh now wait I just picked up a little this is so funny I just picked up a little Canadian when you said England I said it the way Dave said says it oh is that why you're doing it because I know it's also a little Canadian as well I think Dave says England the way that many Canadians say England that's what I thought but but I was I was just identifying that as maybe the derivation of why Dave liked him you know uh yeah it was a little yeah it's a little bit of call me a little bit of column B but yes absolutely got it um yeah well I've been loving it and I will say that you know I guess what I the uh uh to use a little self-help speak the journey that I've been on over the past uh eight years uh you know has been uh uh uh it's been it's been fascinating because it's been almost like like I've NE like suddenly I'm it's almost like I was just dropped into the TV business because even though I was doing all these other things I was doing the Tony Awards and I was doing you know I wrote for the Oscars while I was working for a letterman and like they again they were very uh generous about letting me do other things that were just with people I liked or you know whatever um and uh uh but but when when when Letterman I mean again it was such a full part of my life that uh I I didn't know what I honestly didn't know what to do next this was always this is always a dilemma when I would talk to students who wanted uh college students who wanted advice about their career and I'd say well what is your what does that dream show you want to work for and they're like well I don't really have one I just want to write for television and I'm like you know there was a part of me I wouldn't say this but there's a part of me it's like I don't know how to help you I think you have to have a dream yeah yeah and then finally at age 45 I was able to identify because uh or 44 I guess I was able to identify because I was like oh this is the first time in my life when I don't have this when I'm not working my dream job so um so I was kind of open to possibility and you know I worked on this uh on this uh this the summer series the Mayan Marty series with Lauren Michaels I worked uh uh Lauren is sort of a side gig threw me uh uh uh producing the Adele concert at Radio City Music Hall while we were waiting for the Mayan Marty thing to start up which was hello I know it was yeah it was quite a quite a little side hustle um no it was amazing that was that was incredible of Lauren um uh uh uh so so was that I was I've been you know written for a whole bunch of different award shows I developed I was working on developing a bunch of things with a bunch of interesting different interesting people um uh shot a pilot uh just a whole a whole variety I actually went and did uh I did a little work in public radio up in Maine because that was something I'd always been curious about so I went and I did a radio piece for like the radio station up there to see if that was something that that would uh that I'd be into um and uh uh yeah so I you know I've kind of been for uh well I worked at The Late Late Show with James Corden for uh a span of uh half a year yeah uh the uh which which was funny to me because I know I had said earlier in this conversation um for anybody who stuck it out this long which I'd find hard to believe but right um uh no but I said earlier in the conversation hopefully Mike's edited it out but I said um that I couldn't imagine working for another talk show but it was funny when there there was a a a head writer opening at The Cordon show and and I thought well you know the show they do it's so it's it's great and it's so different and I was reminded of Dave how he would he would say back on the old show I don't sing I don't dance and I don't like being around people who do right and I thought this is the exact opposite of that you know this is a with a guy who sings who dances and he loves being around people who do yep so I you know I thought that would be fun and it was fun it was it was fun um uh it was another it was just being dropped into another world that like another one of these machines that just like Works beautifully unbelievably talented people um you know laughing all day long like it was you know it was it was great it was great um but at the end of like you know I don't know if it was I guess during coven or you know I don't know if it had to do with covet or if it just had to do with uh uh distance from leaving the show ending and everything um but at a certain point I kind of I think I've came to the realization that like maybe the next thing maybe I'm looking for the wrong thing maybe I'm looking for a professional thing that is going to make all of the synapses in my brain go crazy and light up when the thing that has been looming for you know uh 25 years in my brain has been live in London live in London and so um I decided to listen to that you know and I'm seeing I'm gonna find out what's happening I've been here about a year and a half now um and I'm absolutely loving it and in every way um it's been uh it's surpassed expectations I'm continuing to do work in the in the states most uh at this point entirely in the States but uh traveling back uh uh to LA and New York or whatever as need be and doing the rest remote from here which is fine it's worked out perfectly um and uh yeah but I think you know I think I think the thing was I was imposing this professional thing on it and really I should have just said what's the next what's the next Hunger that I have and it was you know it was sort of staring me in the face all this time and so you know the Lettermen thing somehow magically worked out spectacularly again all credit to all the people who helped me fulfill that dream sure but um uh you know I'm kind of thinking so far based on what I've seen in London this has been the right call too and it's just been about it's not been about uh career it's been about this other poll you know so well you know it's it's exactly the opposite uh but exactly the same thing as what we started the conversation with uh you know you're in New York uh you don't know how you're gonna make rent um all you know is you want to work for Letterman and then the career stuff worked out okay now you go to London you're not sure how the logistics of things career all that stuff is going to work out but you know you want to be in London and then everything just sort of starts to work out to me the common thing is delve into yourself what do you really want what do you want more than anything and then go for it put the actions towards it uh you know bust your ass for it and everything else around it will just sort of work out to me that's what that message says I don't know if that resonates or not yeah no I think it's you know I think maybe it was maybe you know the simple rule if I apply it so far and again I've been here a year and a half so I haven't quite been here the 20 23 years that I was on Letterman like I don't have that kind of perspective to look back on and say whether it's worked out or not sure but but I think if digested applied the rule of where do I where do I want to spend the most hours of my day you know that would have been the Letterman show wherever it had been if you know it could have been in Topeka Kansas and I would have said that I want to spend my day in Topeka Kansas because that's where Letterman shows um and in this case it was like where do I where do I sort of fantasize about getting up in the morning and that's you know London and so um I don't know if it's the good people of Topeka of course no no no I'm sure I haven't been so I can't really even speech I don't mean to I'm not bad-mouthing you no I just thought I'd change it from you know Trenton would have been what Dave would have said it would have been Trenton yeah this one more than Topeka isn't it those pure people have had enough abuse from us over the years so we'll just go with Topeka but um uh yeah anyway uh yeah I don't I I was I had some little something oh I'm sorry I derailed no no no no no no no no no no it wasn't it wasn't oh oh I was just going to say a a college professor of mine once said that he said pick the place where you want to live and then figure out what you can do there to make a living and I I mean that was never an option for me because I the place I wanted to work was only in one place but I think as a rule if you're not working in a you know if it's not a career that is site-specific um I think that's great advice because at the end of the day you want to be happy uh in your environs and you want to be able to you know you want to be at sort of Peace you know I mean New York was always very challenging for me uh you know I by the time like particularly when I worked at 30 Rock after Letterman uh with Lauren Michaels projects by the time I got to my office at 30 Rock I was I just felt like I don't I can't see another person for the rest of the day it was just between the Subway and then The Concourse level and getting to the elevator and getting up you know like it was just a lot of full-on crush of humanity and I think at that point I was just a little like I think I'd kind of been you know I'd I'd had I'd had enough of New York for that period of time I still love New York but uh of course I love I love going back to New York um but I just feel like you know I think I think all of it had kind of built up and I think I was ready for uh for for just a change just to try something different you know try something different for a while so uh well I'm congratulations on having the ability and the and the and the like listening to the wisdom because again the thing about wisdom is that you know you get people who give it to you it's it's up to us whether we take it or not and for you to take that advice and and again the courage to Chase the Dream uh like you've built that habit from when you were a kid you know congratulations on that that's fantastic um do we have a second to talk about the hypnosis thing or or are we done sure yes no no let's ask me about the hypnosis thing you know I said on the on the on the peace Walter did with me um and Barbara was there too by the way which she always understates her importance in these things but she's a a great presence I'm really glad you mentioned that uh uh so uh uh I talked to them by the way for two hours so what you saw was just the eight or nine minutes of stuff that they then supplemented with clips that you know was out of two hours so oh yeah um from them about you as well well I don't know any of it was good enough for that but but the uh they might have just gone like oh we barely squeaked out the 20 minute segment but uh um the uh uh the thing that I said there was you know everyone loves the hypnosis remote except me yeah um because I don't know I just find it absolutely uh uh uh yeah I just find it more defined but yeah uh so what what did you want to know about it okay so no okay so I'm gonna the mortification part we'll set that aside for a second here you have no reason to be I am uh because I think I got a couple I think you had a couple years on me I'm a 76 baby so like how the time when the shift happened for for those who were in their formative years that's where a lot of the you know the cult fans and things like that um enthusiasts have come from is that time I was right in the middle of that that's like bang on when you guys moved over the first few years of Late Show were just beyond for formative years for me I've just graduating high school at the time and I'm over at my buddy's house he's got this kind of basement uh part of his of his parents house that he's in he's got the full run of the basement and I would go over there every single night and watch Letterman um and and and we were recorded as well because there were times where there was no DVR and and I mean we wanted to go back and watch this stuff the hypnosis bit I bet you we watched it 50 60 times in the first two weeks that it there um because we were like okay trying to figure out what was real what was you know television magic what was like like when okay when Dave was saying sleep on the air again like I got to be careful saying sleep because I don't want you to fall asleep like suddenly yeah exactly yeah like they do a shot okay there's Biff on the couch that's fine but then they do a shot of interns sleeping and we're like okay that's obviously put on for the show but then someone told me that that was not put on for the show and I think that they were trying to lead me along in doing that no okay no because what they did is they got they got Marshall silver yes on the phone yes and they but but they had him talk to me and um was the was the interns named Don maybe I think maybe the intern's name was Don but not mistaken maybe I've got that wrong but anyway uh they got both of us on the phone and he did the whole he went through the whole hypnosis thing with us on the phone so he kind of got he he'd done it he he he virtually entranced us or or telephonically in transits or whatever you want to say but but again it's not so much again it's a uh I don't know how to say it other than it is it is suggest it is taking suggestion that's the best way I can say it it's like a it's like a it's like a relaxing and then taking suggestion and then and I don't understand the mechanism of it I don't understand the mechanism other than to say that there wasn't anything there wasn't anything that you saw in that remote yeah where I was like suddenly alert and they're like okay we need you to go stand over there and just pretend you're hypnotized again and then we'll just shoot you doing this stupid thing there was nothing like that with me with Biff with there was no there was no there was nothing like that everything you saw everything so I'm laughing because of a random uh sorry it's the most random number um I'm not even going to bore you with it at this point but um I just just something popped in my everything you saw really happened um uh so even during the show real time the show's recording and and and so he says that Biff comes and slumps in the chair you're in another part of the building and you've fallen asleep as well is that what happened I don't I don't know that's how they edited it and and so that was the part that I was like okay because like because you know how you know Hal would do the great edits and perfect edits and obviously they had a camera somewhere on you guys that's the part that I was I was more curious about in that segment well okay I the uh the honest answer is I don't remember okay imagine the only thing I can imagine is you have to keep in mind that because this wasn't a planned comedy bit right it was no time set aside for it in the show so whoever the and I'm guessing it was Barbara I was just gonna say whoever the the The Unlucky producer was who had to edit that night's show I bet I mean I don't know this would be a good question if Barbara uh when you talk to Barbara um is just how much was that night show up because I bet I mean I can't imagine what had to be taken out of that show and if we did all the guest segments that night they had to be preserved and so my my guess is they may have they may have abbreviated it so that you just come in and we're also you know uh out but I don't think it was it wasn't I don't think there was anything calculated there to like hide anything because there wouldn't have been anything to hide it just might have it probably was just to get this show on the air it was probably just to get the show done in 44 minutes or 42 minutes or whatever it was so expertly edited and expertly put together like again if there was a perfect talk show moment that combined spontaneity with well planned with the comedy God smiling on you and adding little seasonings as you put it like it was absolutely effect again but again my formative years whatever that's one of my very very very very very very favorite moments of that entire run from both shows is that that particular one so it was great seeing you it was great seeing you be the guy that ends up being the head writer uh to me that is just beautiful beautiful natural storybook life uh moment and I just I I Adore that um I know Dawn wants to come in and ask you one thing before we're done if uh if there were two or three people that you would like to see Dave do long form is there anybody that you'd be interested in seeing him do that with uh yeah you know I gave some thought to this uh I guess the easy ones to me well I'll give you three because I I also watched other people and I thought you know I mean you know Harry Letterman is a great choice that's a no-brainer I'd love that but but I won't make that one said that too yeah I know no no no but I'm not making that one of my answers because it's already been said and I think it's great I think it's better than any of my answers though uh but I'm just I would I would I would put that on the list but um but I uh I was thinking like if I was thinking Warren Buffett was somebody that Dave never got on the show and Dave was always so interesting talking to uh people in positions of power and Warren Buffett I think is unique and that he's so he's kept such a low profile and and he's lived in that same house and all that stuff and you know he dresses like he's an insurance salesman from Trenton and uh um uh so Warren Buffett would be on there great answer I think I was gonna say it'd be interesting to see him talk to um I always like it when he talks to people like I was going to say Oprah again yeah just because they both are now getting to a point in their lives that I feel like there might be a really interesting conversation just to be had about almost an existential conversation about the lives they've had you know yes uh her as a local news personality and him is a stand-up and and how they've they've achieved everything they could have imagined and more and then now you know uh uh their life was closer to the end than it is the beginning yeah and and what does that all mean what does what does the success and the wealth and the like what you know what what what after all these things that a lot of people would say like well you've got that you don't need anything else what more do they want what more do they value why do they want to spend their time I think that would be a fascinating discussion absolutely um and then I was gonna say this might just be for me but um uh uh and this might also just be a very topical one but I was trying to think of like who I would you know and I was thinking um uh Elliott page because I thought yeah uh uh I always thought Dave was great especially at this time right now in in in American culture particularly where you know I think people are I think there's there's a lot of missing empathy for uh trans people and uh and so I think you know I I think also ignorance yes yes and not not ill willed ignorance just just flat out lacking up knowledge that's actually better said is is it's genuine genuine ignorance about the experience and yeah I think Dave always brought um he brought two things to you know he brought many strengths but two of his strengths were the ability to understand the whatever that sort of Centrist average American kind of way of looking at something might be but then also uh sort of an elevated intellectual uh uh smart thoughtful empathetic way of approaching an issue too and he did a great job of marrying those two things yeah and I think that like it you know I I like to think that that resulted in more understanding about issues you know and things and uh it certainly has for me personally and a lot of my friends who love letter that's one of the things we love about them yeah and I yeah exactly and I think you know I just think uh now and that's not to say that there weren't guests who already you know there were plenty of guests who took ticked boxes like that on the show but I just think now especially in long form uh and also with David a place where you know he's a he's a guy who learns you know he's learning constantly and he's you know never you know he's an intellectually curious guy and he's you know extraordinarily well read I just think that would be a fascinating I would like to see that conversation I don't know that there's anybody else out there right now who would do as interesting a conversation with Elliot page as David could not agree more actually that's not that's not fair that's not fair but I guess I guess I just think how about if I just limit it to a straight guy that would do a you know a straight CIS male would not there I think he'd be a very interesting person to do uh to do that conversation with without a death and and again like you say um like a bridge builder because there are so many people that that can take that same perspective these questions get asked from that perspective and new levels of understanding could show up plus I here's the other X Factor part he'd make it entertaining he'd make it fun he'd make it he'd make it absolutely great and that's the thing that I that's one of the reasons why uh he would be perfect for that by the way um I don't know if Don's gonna pop on now Don we're gonna say goodbye to Matt here in a second but like there it is right there yeah exactly well it's lovely and the facial hair by the way is fantastic just so you know I know you kind of mocked it on your thing that is that's do you want to see a kid of the 90s ladies and gentlemen that's him right there that's a child of the 90s right there um Donna's we're closing up with Matt what did you uh did you want to throw anything out there yeah sorry Matt I couldn't help it um it's probably not the worst increase frame yeah it's probably not the worst freezer that's a good one yeah um I'm amazed that you remembered uh I don't sing I don't dance I don't like to be with people who do uh that you know where that comes from uh yeah he was preparing for the Emmy Awards in 86.

okay and when he was co-hosting with Shelley Long and and for like the week before he said it constantly and then when he when he appeared on Johnny he said the same thing um so it's a classic line well that's incredible and then what I I love that you put in that context because it means that I was 15 years old I heard that and that it stuck with me it stuck with me all this time you know it really made me laugh the other thing I wanted to ask him and and believe me this is not to diminish your own achievements I want to make that really clear no he'll do a good enough job doing that himself it's okay um when you got the head writer job on Late Show did anyone else want it wow wow John wait no no I want you to sort of explicate that question let's see in 97 uh I was invited to come by to uh help celebrate one of the new guys on the show Justin and I came on it was it was in The Writer's room and and at the time Tim long had just begun the the job and I remember that that uh a few months in he's losing his hair he's maybe losing his teeth it was it was doing bad things to him uh and he left and I don't remember who who followed him uh before the stangles um I I know that there were some issues with the stangles and and we don't need to get into that but they finally left and that's the impression I got I got and from people who I asked um uh yeah the impression what I got was that you know nobody wants this this hell you know nobody wants this one so you're asking your question is did you draw the Short Straw to become handwriter yeah yeah no and I don't think uh uh uh no I I think you know uh jeez no I I I I think any writer at the show would have been uh elated to have you know to I mean I'm not maybe they wouldn't have I'm not necessarily saying that every writer through they're having a ring and uh you know I don't know the honest answer is yeah I don't I don't know but but for me anyway uh it was not uh it was not something I didn't want it was uh it was something that uh I you know uh uh I was excited to take on and I have to say that when I moved into that position it was again I apologize I just sound like all I must do is resell helpbooks but but it was that um uh and it's really only what I do with half my time um so the the uh the flow this the whole uh mahali uh six cent mahali thing the flow right the state of flow um uh and I'm mauling the name of that writer but uh uh but uh I don't think I've ever experienced that the same way in my life I mean it was it was honestly just decisions just at a pace at which I mean the only other person at the show who I can imagine must be in a situation like that and and probably much worse because he's doing it in real time but is is the director of the show like you know that's where you just have decision decision decision constantly um but as far as like a non in real time job I mean it is all in real time because you're putting the show together but I mean you know not not in the broadcast Booth but in in over the course of a day it just was it was just it was just Relentless it was just um but in a way that was so uh so satisfying I mean I I just can't even begin to describe I just loved it I did you know it says thing where there's barely even time to eat like there's no time to eat lunch like you're you know uh I had a great assistant um Alex bully and he was like he was a great assistant because not only was he funny and on top of everything but he was like three steps ahead of everything and so you know uh he would be he would help me like have make sure that there was something there to to shovel into my mouth while I was well I was looking at the things he had stacked up carefully in front of me that like you know and uh it was uh but that's like what it was it was just like a marathon to just get everything done and yet it wasn't in a miserable way it was like in a in a uh yeah you still have your hair and and let me see your teeth I'm talking 1997 and and what the you you got the job in 2013.

so with so it's it it's it it's it sounds it sounds like it was it was two different errors oh well the show I mean you saw how the show changed I mean you know by the end we weren't doing fun with Rupert we weren't doing thing you know we weren't doing things as much outside uh the studio on the street whatever else I mean but again like any writer uh and and I'm not suggesting I was the only writer by any means but as any writer will tell you the uh uh uh you know restrictions can sometimes be your friend because you know they force you to give you some context in which you you know so you know did it frustrate us if we had some amazing idea that we knew Dave would just knock out of the park that was outside the building and we couldn't do it uh you know or that would have required traveling in a way that we you know we weren't kind of doing at that point yeah that was frustrating but at the same time it's like okay but there's always been things there's always been things we could and couldn't do and for one reason or another and uh uh uh uh yeah it was just that you just have to accept it and move on um yeah no when I was in college there was a music teacher who who said accept your limits embrace the limits and respect the limits and and you'll get things done within those limits um and that's something I've I've ignored since um have you have you already discussed uh the weekend Late Show because if you have then I don't no we haven't it's on my list of things there's like five things on my list that we have discussed weekend so after I put together the compilation uh I got a comment from someone saying I don't get it what's the point you know do something funny and and I was thinking you don't get it you don't get how brilliant this was exactly I mean listen to that dialogue it's it's subversive and it was it was I loved it and and uh only later did I did I find out that that was your creation so I just wanted to say Bravo for that oh thanks well I'm glad you enjoyed it I mean it doesn't necessarily have to it does you know again I I don't you know I think the whole thing is uh the whole spirit in which the show existed was that you know it wasn't necessarily for everyone you know it was uh that's why you felt like you were in a club you know so that's why you know I think there were you know there were things that people people loved and hated the quiz machine even with our within our own staff you know so I mean you know so no that was Universal there were probably people who hated the weekend Late Show on the staff and uh um uh yeah any Dave loved it and Dave um Dave particularly liked it when I don't know there was I don't know how many episodes in it was when it took the turn where we where Bruce says something that I think Bruce says the kids are with your mom this week in one of them sort of like in one of the what sounds like an ad-lib back and forth and Dave and Dave Dave did you just love the fact that like this sort of B story was gonna it was coming out between you know we were just hearing about Bruce's marital problems in the promo for their d-level weekend so anyway I I don't know I'm laughing because it because you know again when when something tickles it was funny it was great well but you also you know you also everybody will say this but when you make Dave laugh about something you know it uh it's everything you want so that was very satisfying when he found that funny the last thing uh do you know the history with Marshall silver and and late night I don't he was on I think in 86 um and Dave was so disruptive that that that silver was not successful in hypnotizing any of the of the volunteers he got from the audience and he was pissed he was really pissed and so he I don't know the inner stories but I know that he came on like a month or so later and was given a second chance and Dave behaved oh wow okay yeah okay so I was surprised to see him uh you know during those I was surprised to see the remotes with him that he had returned a wholly different atmosphere he had all the all the support he needed um and maybe because Dave was not involved yeah well or maybe you know it was the was the you know the the approach that they took was the same approach that I've seen hypnotists do at like colleges and things like that which is where they basically Begin by um attempting to hypnotize the entire crowd because then they can see and that's what we did if you wanted to participate we all went down to the studio and we all stood in the studio and he went through the the sort of Trance thing and then and then he's able to see who's who is uh most successful right engages so that was that was how then that was how I got selected out yeah yeah all right um and the last thing it's more personal and and uh I won't go into it too much but only to make you uncomfortable um am I getting laid lately is that the question well no that's the poll line I'm not going to do that um way to go Paul yeah that was so great so great when I was persuaded to put up my GoFundMe page you were the first you were the first one and I'll never forget that I'll never thank you enough for that and and what you did helped open the floodgates for other staffers to do the same so that's something that uh you know uh I'll stop saying sleep uh so thank you for that oh Don you're very welcome you didn't need to you didn't even need to say that but uh you're very kind to say that uh Michael you still put up the photo of me looking like a again we're even yeah yeah exactly thank you for saying that Don thank you for coming on thank you wow that was really that was that was damn sweet um so speaking of damn sweet uh Matt you have been so unbelievably generous with your time tell me you got a good dinner or something coming up to to reward you karmatically for uh doing this active good service for all of us who are enthusiasts of David Letterman what do you got going on tonight in London huh even better actually in about an hour and a half I will be arriving at the um at uh at a whiskey tasting so uh lovely yeah I mean I should say it's now almost five o'clock here so this is uh this is 6 30.

it'll be 6 30 p.m this won't be like uh it's not two in the afternoon uh yeah it's an appropriate hour of the day but yeah it's gonna be a uh a whiskey tasting so it'll be is there a language problem with you being there well I mean uh uh no not too much of one not too much okay he doesn't spell color with a u so that's a problem does this say process uh this all of it all of it all of it uh I I was on an escalator yesterday going out of the uh uh uh going out of the tube and usually in the you know they follow rules pretty pretty uh explicitly over here usually people stand on the right on the escalator and then they leave the left open for people to walk up and so I was walking up the left and then all of a sudden there was someone stopped and it looked I looked just ahead of them was a a a couple with one of those double wide strollers baby strollers so it was taking up the whole escalator there was no way to go around them you know so uh uh uh a woman walked up behind me and stopped behind me and I turned around and I said uh I think there's a a double stroller on the escalator and then as I'm looking I turned back around and then I was like I don't call it a stroller here what are they called oh and then I turned around and I said cram I meant pram um and she goes yeah no I I got it I I guess it was important to me it was important to me to correct myself so I find you know there's a lot of me doing that where I'm like uh you know no on the Bonnet of the car I'm sorry it's on the Bonnet of the car there's a lot of me doing that gotcha all right oh yeah okay I almost made an f word joke that isn't the f word that we know it's the f word over there but I'm not gonna do it um hi anyway uh you I hope you enjoy the whiskey tasting I hope it's absolutely awesome that I'm envious um I love me some scotch and good scotch and and and looking at the differences between them all I hope it's just the right level of peat for you uh at your favorite one and you get lots of it um you'll come back and do this again I know I'm saying it while the record button's on so you have nothing else to say but yes that is one of my techniques uh Matt like seriously I have a bunch of things that I haven't talked about here you've really really made my week at the beginning of my week thank you so much for coming on I hope we get to do this again and again uh from the bottom of my heart on behalf of all Letterman enthusiasts out there thank you for your contribution tremendous contribution to this thing that we all love so so very dearly thank you so so much for being part of uh of the company part of David Letterman and Company uh well thank you Mike that's kind of you and uh it's been a pleasure revisiting all of this with you and and as I said your your appreciation is uh is is infectious and it's uh and and it's fun to it's fun to look back on the show Through The Eyes of a fan again so you know that's that's great we appreciate that uh a fat it has to be a fan who does this show one of you guys couldn't do this show ever you you'd never be able to do it it just wouldn't happen um but it's it's it's it's fantastic to be uh you know fan I put the fan in fantastic I suppose thank you so much I appreciate it I'm gonna hit stop right now we can all say goodbye Matt go get laid okay okay for those of you who made it this long uh made it through to the outro and have decided to stay on the outro and listen to Mike the blowhard continue to uh to talk a little bit before this episode is over uh was I wrong you know to quote Walter from The Big Lebowski Am I Wrong uh no that was a fact tick conversation I can't wait to have him back I can't wait to have Matt back I just um everything about that was just so insightful and delightful and uh all of the foals really um and I'm grateful that he took so much time uh for us and it just evolved I mean you know I I tell these people hey let's block out an hour you know and and if you have more time it may evolve into more and when it does it does so organically and it's so fun um yeah we're creating uh an anecdotal archive here um of of uh the greatest body of broadcast work in history that of David Letterman and Company it is my honor to be a part of this in any way shape or form uh please join the Facebook group I'm going to be throwing up some uh some more videos and things people have responded back to some of the things I've thrown up in there um and affirmatively and I think if you're a fan of uh of Dave The Works of David Letterman the stuff that goes up in there there's some cool things that are happening and we've got some more stuff to go into um thank you very much for being a part of this episode I can't tell you how much I appreciate it I hope you have a fantastic week we've got some great shows coming up thank you so much uh my name is Mike Chisholm uh I'm the host of the Letterman podcast with Mike Chisholm thank you and good night overcoat and Underpants