Tom (Tommy) Ruprecht

welcome once again to the letterman podcast my name is mike chisholm i am stoked to be here and uh do this to talk about all the things all things david letterman and celebrate like i said i'm a broken record with this crap but i say the unprecedented body of broadcasting work i truly believe that it's a good time to be a dave fan uh in 2022 who knew that we were going to be saying that but we are and i've got a really awesome guest on the show today they're all awesome guests of course uh but here's a guy who wrote for the late show for uh 12 years of baker's dozen years something like that 10 12 13 years something like that uh tom ruprecht is going to be on the show today but before we do introduce tom um who i don't know if he goes by tom or tommy but we'll find that out here momentarily we're gonna do a quick sponsor shout out um the uh the loan sponsor so far but it's a doozy of the letterman podcast is the hello deli uh we wanna thank rupert and may for everything that they do they are a sponsor of our show uh this show is brought to you in part by them and uh hey listen did you break your late show mug did you uh you know buy go to new york and get a late show with david letterman's shirt and and it's just been years since dave's been around and so there's holes in that thing whatever did you know that you can go to hello deli.com and you can actually get late show with david letterman merchandise one the only places in the world you can actually get officially licensed late show with david levin merchandise you can get rupert shirts all sorts of stuff if you're from the new york area go to the hello deli go get a sandwich go say hello to rubert may and uh if uh if you want some of this merchandise back again do you need a late show cap they're stylish and they advertise that you love the late show with david letterman you can go there right now hello deli.com and get yourself some official david letterman merchandise uh i feel so good i don't feel cheap or used at all after i plug that sponsor it is the greatest thing in the world uh i just appreciate rupert and uh and we've had irene uh rupert's girl irene on here a couple of times already um and i just thank you very much rupert for sponsoring us we appreciate this it's a lot of fun now now that the uh the chores are done the heavy lifting is done it's time to get to some fun tommy tom rupret thank you so much for coming on our show today i have i can't tell you how big of a thrill it is for me and be conversing with you man and i i would just like to say your heavy lifting is not done because i am not going to give you an inch you are going to be pulling teeth this entire interview yes i'm not going to crack outstanding oh this is phenomenal i uh i i i go by tom or tommy whichever you would uh prefer okay uh fair enough i i every time i've seen like when uh when strahan and them were were saying goodbye to you it seemed like they were calling you tommy i i yeah i think uh yeah i think people who know me ten tend to go go with time people who actually have talked to me and know how immature i am they they tend to go with tommy but i guess i i i uh whenever i write something i usually sign it tom to try to give me and just just a smidge of credibility a little bit of professionalism yes exactly uh well that immaturity goes both ways sir and uh and and i appreciate that i appreciate the fact that you're so enthusiastic and have this kind of unbridled enthusiasm i i share that same uh that same gifting um i want to get into it so so you were a long-term writer on the late show yes i was i was there for a while yes incredible uh and some of the things that you have seen i want to get into some of those those highlights here and and whatnot but at the end of the day every single time we have a former staffer on here uh i want to know what how you started working there and i know that's a cliche question i hopefully will be able to ask you some stuff that you haven't been asked before but but i think it's really important for people out there to understand how some of these people got started and and became associated with uh with dave and company so okay how did it start for you um i actually i mean you know uh i was a fan of the show and when i was in college i was watching the show and you know they did they did a piece where they mentioned the interns and uh and that kind of you know fired off synapses in my brain like wow i bet that would be fun you know little do i know but um yeah so the the show was on at nbc at the time so i called just the main line at nbc and some nbc person invited me in for an interview and i did that and they liked me and so then they put me on the list to interview with the the letterman people and so i got called back in to do that and actually the person who i believe you interviewed like last week or daniel kellison yeah uh he interviewed me and and the way the way it works is like there there were like internships for like eight different departments at the show and so what you would do is you would come in as a prospective intern and you would do the round robin you would interview eight different people and hopefully one of those eight interviews would go well and one of those departments would want you as an intern so my first interview was with daniel and it was fine and daniel was then supposed to take me and hand me off to you know the next person and then i would have eight interviews you know i i didn't know so i interviewed with daniel the interview finished and daniel said all right now what am i supposed to do with you and i went i don't know because no one had told me but daniel was supposed to know to hand me off and so he goes all right i'll walk you the elevator you know and and so i left and only later did i find out that like instead of having eight shots at an intro i just had one now like and that i had just dramatically uh killed my chances but uh uh fortunately daniel liked me well enough that i was uh he picked me oh my god okay so he was out of research at that point he was a segment producer at the time then he was yeah he had recently been promoted yeah he was he was he was a new relatively new segment produ yeah i think he actually yeah he had just gotten the job i think and uh and so yeah i was now doing research for daniel to try to help uh help him uh you know find information for uh guest segments what year was this about approximately this would have been 1989 into 90.

we got to do it a little bit with uh with dan but but at the end of the day researching back then a completely different planet different solar system to researching now yes um i mean my gosh see now this process this was this was this was the days before the internet yeah um it was also the day this is something you would take for granted now because everything's on youtube but back then there was no youtube and like one of the charming things on like our show was it was a place to occasionally see during a guest interview like someone's like first appearance on tv like you know like you know you know such and such you know so and so before they're famous maybe they were on the dating game or something like that and so one of the jobs of the research was to try to dig up all that old footage which back then was really hard because the all these all this footage was just kept in warehouses of various production companies and so you would have to like see like okay 20th century fox owns the dating game and you would have to find the air gate and then call somebody and then just like try to convince them to go to the warehouse and get the clip out cut the clip and send it to you and it was like a very arduous process and um and that yeah that was it was a lot of leg work like like trying to track down that kind of stuff and now it's just yeah it's all on youtube and and but and also it was it was research because there was no internet you were just kind of like you weren't just researching the guests you were also just sort of like the librarian for everyone at the show just everyone at the show at the show who had questions that today they could answer on the internet they would just call you with just random random you know stuff and like i remember once dave was thinking about getting a place in montana he which he's been very very happily you know and yeah uh and i remember his assistant called me and because i was in research i was the guy to ask she asked like will bears be a problem in this part of montana and i was like geez i don't know and so i was like what am i supposed to do and so like you know she named the town and and i called i called the hardware store in the town and like as as i'm talking to them i'm knowing what the answer is gonna be i said like hey i'm thinking of buying a place in montana i'm just worried you know our bear is a thing you know and as i'm saying it i know that i come across like this jerk jerk new york jerk and like and sure enough the the guy in the hardware store is like you know hey harvey this is a guy you know and they're all laughing at me and like oh are you scared of bears and everything and so then i get off the phone and i call dave's assistant and he's fine by the house there's no bears dave buys the hair the house and then i don't know a few months later he's in the house he walks into his kitchen and there's a freaking bear in his kitchen exactly little did he know i felt kind of bad about that oh well i guess i wasn't very good at research i think is what we're all getting at um okay i want to know how long did you did you do that job for like clearly with your personality and all that i can see how you would have evolved over to the writers and all that stuff but how long did the research uh job last uh probably like three or four years i guess oh wow because you did it for a while yeah okay so when you took that job did kelson basically hand you a rolodex of contacts of some of these different places that you could go to or was it you building relationships with some of these folks uh along the way who were the gatekeepers of whatever this information that you uh yeah it was a little of both you know like daniel gave me a rolodex but then you know you know daniel's personality so you know often he had burned those bridges you know i was now starting from scratch last thing i wanted to tell them is that i i was friends with daniel kelly no uh no danny daniel uh i'm sure this came up in his interview but like there's no better segment producer in television history i would bet like no one crafted a better segment than daniel and so it was just it was a thrill to kind of get my start working uh for him and it helped me just immeasurably yes i'm having so much fun with this process because uh i am such a big enthusiast uh of course of what you guys all did uh but but through the process of doing this show i talked to many of you guys and hearing you give shots back and forth to each other good natured shots like like i i described this you know you guys had a family and we we've talked about this on the show a few times uh it's a lot of fun to be the relayer of these types of messages and things like that and if a fight begins at some point because of me doing that either knowingly or unknowingly you know being used as a pawn by one of you guys i think i think that my job will be done i think that would be a good thing if if an actual fist fight between one of you guys begins i think that would be good there will be no offense in fact like just to show you like like daniel like um a bunch of years ago dave got the mark twain award down in dc and um and like dave very kindly asked me to like help him with his speech you know and so i did and um and we were down there during the ceremony and and jimmy kimmel was there he was taking part in the thing and daniel was with jimmy kimmel and uh jimmy kimmel remarked that he like he really likes something in dave's speech and like daniel like dragged jimmy kimmel all the way down these hallways just to bring him over to me and be like this is tom rubrick you should you know he's the guy who did this and it was just like so kind and like daniel has done a million nice things for me yeah yeah you talk about that we talked about that on on his episode too with um he is eternally uh in charge of paying it forward because steve o'donnell did that for him and and and i just thought that was such a beautiful thing how how how you know he was a no an intern just come in there didn't know anything thought he knew some things uh wrote some things you know to try and impress and o'donnell actually took time to take him out for lunch and say okay and he went through the whole thing with him and and um and showed him so much kindness and he said that eternally he will do that for people uh because of that and that is not an isolated incident with you guys and gals um i hear that all the time he has a very cool atmosphere that that you had people around you who you know whether or not they were there for a long period of time or their job was just to hold the baton for you know a few hundred meters and then hand it off to somebody right you guys really did seem to uh be to take care of each other to be there for each other it was it was it was nice because you hear like i never worked at saturday night live but like you often hear that it's kind of a cutthroat environment and and um i i mean i don't know if it's it's testimony to having to do a show every day like like at at some point you're gonna need favors from everyone on staff just because like there's just so much chaos and and and you know and and so like it was really really a nice place to work like everyone really looked out for each other and like that's why you know i stayed there a ridiculously long time you know i was probably there total of like 17 years which is crazy in tv to stay someplace that long but the reason is is because you know i mean that's they became my friends and i ended up you know marrying a woman who worked there and uh you know um yeah it was really a great environment i love that uh i love that so much and so you were you made the transition then from nbc to cvs i no i didn't so my internship was nbc i then haven't finished college during when i was finishing colleges when the show switched and then soon after they got to cbs i graduated and then i got uh um once again daniel was one of the people who helped to bring me in uh to get a job there yeah that's that's that's amazing um you know i don't know if there's a more historic moment i mean i love carter's books and i love i love looking at the history of it but but living it like i don't know if it's if it's uh underrated or not but when people talk about the biggest moments that happen in television history or broadcasting history to me that is the number one moment to me that is the the the the pinnacle moment of a shift you know carter's book originally the late shift right i mean so prophetic in its title it wasn't just hosts moving um and and what not the entire landscape change the franchise again i go off like a broken record i go deep on this one um franchise had never ever taken on the tonight show and made any sort of dent in it at all never mind the number one stuff who cares about that nobody had ever competed yes and then when that shift happened um you know monumental i i do think it was it's one of the biggest moments in broadcasting history uh you were there early on what was the pressure like when you you know before you kind of settled in and got if you ever did get comfortable i don't know if you ever did but what was that pressure like when you started working there was it just all hands on deck us versus them was that part of it or was it just we want to do right by dave and help him put on a great show i know how loyal everybody was like yeah i mean i guess yeah there there there was yeah there was a leno there was yes some pressure with leno and competing with that but i i really you know that was kind of a macro existential pressure but i think what you felt day to day was more the pressure to do a good show and then also just because because dave is extremely demanding and you know hard on himself and hard on the material and like is continually like or would continually like rip stuff out and like you know we'd be rewriting the show a half hour before and so a lot of the pressure was was was generated by kind of that yeah that was the prime driver of the stress yeah the desire to have the best show possible uh and then do it again tomorrow and do it again tomorrow and do it again tomorrow the groundhog day effect must have just been bonkers it was yeah it was weird because you would you would just like you would finish the show and you know we would tape you know in the late afternoon and then you'd come upstairs after the show and it would be like 6 30 or something and then you'd be like oh gosh we have an empty sleeve for tomorrow and then we need to put in a couple hours now to just try to you know and you're so burned out uh yeah that it it it truly was yeah it was a big grind what um when you by the time you go i hate that we i'm sorry that we're jumping around here so much but i'm just so excited to be doing this and and uh and and hopefully this will be the the last time you come on here we can pick the brand to get a little more granular but okay um what would it when you were writing for the late show when you got to that place where you know you were a regular writer all of that what what did your day look like did it start early or were you a typical like stand up type uh type mentality where you work real late and then sleep in a little bit what did it look like uh okay that's what um i'm just i'm i'm gonna give you a a an answer in parts because it shifted great it like when i first became a writer it was the day would start usually 10 in the morning but we would go till 11 or midnight um we would go late it got it kind of shifted downwards um it it then became we would go in 8 30 or 9 in the morning and we would leave it like eight you know that kind of over the course of the show it shifted it shifted that way yeah okay um and you know when you get in in the morning is it a continuation of the stuff you left on the desk like would you kind of like a game of pool give yourself a bit of a leave for the next morning or or did you was it basically in the morning okay here's what we're doing absolutely um it was it was usually uh the show what we would write would be kind of broken down to i don't know what exactly the percentage is but say maybe 60 40 maybe 60 of the stuff is kind of what you would call evergreen material which it's not tied to that day's news so that's stuff you can write beforehand and then maybe 40 of the show's content will be stuff based on that day's news so most of what you're doing usually what you're doing after the show at night is is kind of the evergreen stuff getting loading up the the cupboard for for the days ahead yeah and then the day of when you get into work that day till showtime is generally spent um reacting to that day's news and so usually what we would do is we would start with a writer's meeting um so you would kind of you would come in and you would you would basically uh you know again this is you know back in when there were newspapers um you know uh you know you'd come in and it would be like cramming for a test you would take 20 minutes going to go into an office and just read through like five newspapers and really sort of get you know a global feel of what's going on in the world and then the writers would get together and then kind of talk about like just a billion ideas of what we should do for that day's show and then you know those would get pitched to dave and then dave would kind of window it down a little and uh and then you know you because a lot of stuff we're doing is like fake commercials and and so you're kind of right you're because that stuff takes a little time to put together um you you would generally like the um yeah you you'd come up with ideas like for fake commercials or things that need voice over and and need to be edited dave would approve you know maybe eight of them sure uh so then you're you're working on those you're writing those scripts you're bringing in voice over people you're you're cutting that uh that voice over and then it's going to take a couple hours for the various people to get the videotape you need to start editing so while they're getting that videotape usually that's when they need to go back to your office and you would write top 10 jokes and you do that for about two hours and um and then generally you would then get called down to the edit room you'd start putting your pieces together that need to be edited um those would go to dave this is like a half hour before the show he'd watch all the video and then so then he has changes and so so like the voiceover guys were all knew to be local uh like at you know like a half hour before showtime because we would call them back to like re-record lines and then we'd have to re-edit the video um yeah in time for the show that is uh you just mentioned a whole bunch of things that don't necessarily sound like they go together in a cohesive day um now i'm talking to some of the some of the folks who work for the show certain people seem to gravitate towards you know uh certain types of of part whether it be the top 10 list or the monologue or or things like that was there an area that you focused on as a part of the writing team well first off wasn't a team or were you guys more run and gun uh competitive that kind of thing or was it a no no you you do this i'll do that well i mean there was um there were there were some things we would write as a group some things you'd do on your own um we weren't competitive again like getting back to that it wasn't really a cut-throat thing like people like people were always willing to help like each other like get somebody you know is stuck on a script and somebody else would give him a line you know um as far as like specialties i used to you know for a bunch of years i would shoot a bunch of the remotes where i would kind of like go with biff to the super bowl and go with biff to the only you know that i did a lot of that kind of stuff um there was a thing great moments in presidential speeches that ran for 20 years yeah that that that was my idea and so yeah i would watch every bush speech because every day we'd need a new kind of like goofy clip for that um i always loved writing top 10 jokes just because it was just you know we knew how to pick topics that were easy to write jokes for and and so you would just like write like 100 jokes in the span of a couple hours and it was just always fun to like just crank out stuff like that i i always enjoyed that i uh i'm glad you brought up the remotes and whatnot and you know what i was going to ask this later in the in the in the show but i'll ask it now and then we'll probably get to more of it and there's probably so many i mean again the idea that you guys turned out so much stuff and then you know even youtube came up while you were doing this youtube wasn't even around at that point so much gold and the reason for this show is the gold that was brought out at breakneck speed and then forgotten well it's time to go back and look at some of that gold and there's so so much of it uh the question is this are are there any remotes like great moments in presidential history oh my god i'm so glad the official channel put out a a super video of that that had you know uh at least a dozen of them all in one i'm glad that i'm so glad that walter and his team are doing what they're doing now um but are there moments other than that one are there moments that kind of okay tom what was something that you uh are really really proud of or that you remember that was just really really awesome that you were uh you were a part of her that you helmed oh gosh i i don't i don't see here's the problem you know i could say something you know i'm really proud of this but then the listeners are going to look it up on youtube and they're going to be like he's proud of that oh my god that's good doesn't matter who gives a that that doesn't matter you know what i really what i really liked um like i didn't like doing the super bowl because that was just so insane it was just it was and then you would have to you'd be shooting till the super bowl's over you'd shoot post game you'd sleep for a couple hours and you'd wake up and you take a 6 a.m flight back to new york and then you'd have to edit the piece in time for that night's show so that was just always crazy i used to love doing the remotes at uh yankee spring training i'm not a yankee i'm not a yankee fan but i'm a huge baseball fan and just the pace of spring training it was it was it was nice to be out of the show for for a couple days which again is stressful and just to be at spring train which is a very laid-back uh uh vibe and yeah that was probably that was like my favorite thing to do that's awesome and you got to know uh i mean throughout the entire show being on staff and whatnot but i mean you're traveling with biff yeah i'm sure you got to know him in a special unique way spent a lot of time with biff yeah that was another another pleasure of the job you know just a wonderful guy yeah rupert g and i are friends and one of the descriptions i have for rupert g is it's like god took the word kind and made it into a human being yeah um biff is another one of those guys where it just what you it seems to me what you see is what you get the genuineness that goes through the camera whether he was sitting with dave whether he was just answering a question for dave with his clipboard or something like that or in one of his segments it seems like the guy that you see in any one of those examples is the guy who he is well i think i mean i i think that's very well put and and i think you're you're sort of getting to what i think is is almost like the essence of the show which you know not that there was a mission statement but i think were there to be one when dave started was taking the artifice out of show business and you know our skits aren't going to be performed by these you know like you know these fake actors it's going to be the guy who's the stage hand and you know showing humans the way they really are um and so yeah that that that was the philosophy of the show it's just kind of like just capturing regular regular things or people behaving normally yeah the the little moments of life that everybody lives it's a communal thing and i think you know going back to the to the macro of it as you put it uh i think one of the reasons why you know they you guys were able to create something that was completely different than the tonight show was exactly that we talk about how you break the fourth wall people on this ship the people we're going to have as guests on this show are also uh folks who have interactions with the show either unexpected or dreamy untrue moments whatever you know the example i always use uh you know dave calls a pay phone right and then somebody picks up the person who picked up that pay phone many of them 20 years later are still talking about it yeah because they had such a cool moment yeah yeah and it was just celebrating every day calling the cleaning lady across the street all that kind of stuff yeah were you part of any of these uh everyday moments where were there times where you said hey dave you should call this person or talk to this person is that uh no but but one thing that you said that reminded me that there was a there's a wonderful guy named hal gurney who was the director of late night and the first few years of late show i had a phone conversation with him three days ago oh oh oh he's then you know he's he's he's the best he's he's another delightful person absolutely so he was also the director when dave had his morning show before late night and he was telling me once that like in the one of the first shows they did um there was um a musician i want to say judy collins could be wrong but judy collins she came on and she was she was singing and she starts to sing and the mic isn't working and so she's she sings her first line and nothing's coming out and dave's kind of looking around and judy's looking around and hal just got on the pa and went uh judy hold on for a second mike's not working just give us a second give us a second we'll get it right and you know okay judy you can start singing and then she does her song and hal said after the show dave like rushed back to him and was not mad but just the opposite was like that's what i want the show to be like it felt real and again it's it's stripping away that artifice of tv and showing you like what's going on behind the scene not everything's perfect you know that yes we were showing warts and all of what it is to do a tv show well and and i think kellis and i talked about this too because because uh he worked with hal on a bunch of other projects it sounds to me like how's the guy that made a made a historical run in broadcasting and then retired half a dozen times only to be brought back to make another historical run on something else and do and show his genius in other ways exactly yeah like for instance like i do in the remotes like um when the when the olympics were in utah you know hal came out of retirement to direct those and so he and i were spent two weeks in utah and then we spent another week in italy when the olympics were there and that was just another just great life experience just hanging out with hal for in these uh locales for a couple weeks he is really great well groundbreaking uh a director of broadcasting but also a character on the show like the fact that um you know i always talk about my big moment there that's behind my my shoulder there by the way also recently not just my moment there signed to my best friend by dave himself that's dave making fun of me there the picture got taken the best part about that well there's a lot of best parts about it but was you know i think if you were to let a letterman enthusiast you would have felt this in college for certain and you're in that audience if you're lucky enough to be the recipient of a hal gurney quick cut to you in the audience yeah uh you know which of course stayed on long after he retired it became a show um you know mainstay yeah that's one of the greatest moments in the entire world and that came from how being a character not just a director but a character who would isolate people in the audience and things like that it's it's such a neat thing that i don't know was done really ever before that certainly not in a in a talk show format where they just loosened it up and the inmates kind of ran the asylum it's it's yeah it's it's it's it's what good can come when you have a director who also has a good comedic mind and hal was able to see like who's someone who's a personality in the audience that i can cut to and you know not everybody especially in those days like you know not it wasn't automatic that a comedy show was gonna have a comedy director you know like yeah i think in those days like they put like oh this guy directed game shows yeah he can he can direct the late night show and and you know but like dave dave was i think very smart like no this guy directed jack parr he he knows how to direct a comedic talk show you know and and and that was yeah yeah let him speak let him be a part of it i think i think that's that's the other thing that i love so much is that uh there was a lot of members of the team that got to do that you think of you think of tony mendez like the body work of tony mendez never mind everything else oh my god that guy uh you know don giller put up a compilation of of tony uh shortly after his passing and holy smokes the things that that some of these um these support people on the show could do did you ever write anything for any of these people like did you ever write anything for hal or jerry did you ever write anything for for tony or did that stuff just uh you know organically grow on its own and become almost you know their own uh type of writing for the show uh i didn't write for oh like jerry mulligan i was like jerry fuller like like the director i didn't write anything for jerry foley because he was a little busy directing the show so we didn't use him as much but okay but yeah like i used to write yeah i'd write stuff for tony you know for calter of course for rupert um but and and so that's that's that's like you know it it depends on the bit like there there are definitely things that are just purely organic where where dave can be doing the monologue and suddenly tony misspelled a word sure on the cue card and then dave's calling him out and tony's firing back and and you know that can become 45 seconds of just purely organic funny stuff but then there are also other times where you set up a bit where you know yes no and the question was more uh like okay so hal or jerry foley or whatever would you ever like build into any of the things that you wrote okay and then they could cut over to this or cut over to that or that was they were separate characters on their own oh uh again there were times where they would find their own thing there were times where as you're writing something you're like oh i think it would be good to have this shot and so you talk to them about it yeah that's cool again yeah it's both it's both oh that's awesome okay um i wanna anybody who was there for the 911 episode uh i i i you know what a segway in transition that is mike well done uh you're a pro let's go from talking about legendary directors and zaniness and these amazing bit players to uh one of the most traumatic moments in in in human history american history uh you were but i i'd be remiss we're 34 minutes into this already i don't know how much time i have i hope uh you know i hope we can go a little longer here um i appreciate it man um you were there you know during the 911 um uh tragedy yes and and for me personally i live in western canada yeah and i can say this with my heart like i was given permission to kind of move on from david letterman yeah and it wasn't just dave it was all of you um i mean i i i'm gonna stop you right there because because that first show back i mean that is purely dave that that that all of that was him talking from his heart and and you know i i think there was no way to kind of write it had to be his his honest human reaction yeah it's hard to write that for a person and dave yeah so they deserves all the credit for because that's that's a tight wire that like i mean before the show started i was like nervous for him like i don't know how you thread this needle but uh no he did he did tremendous absolutely um and and one of the many ways that he has proven uh that he's the greatest broadcaster in human history yeah uh without a doubt the question that i have for you is watching the days and weeks and months after 9 11.

yes um knowing the the crazy dynamics of cultural uh and and the stuff that was making the news uh how you guys uh treated george w bush president george w bush beforehand uh versus after that moment and you know i even remember it was transitioning it felt like it was two or three weeks after that first show where dave was like okay paul can we try a joke here should we try a joke yeah actually note it yeah what was that like in the writer's room for you guys as that time was passing by as the the reality the new normal was setting in yeah were you guys constantly still writing material or was it a day by day thing uh yeah it was yeah we were writing materials because because you had to but yeah it was a day day day-to-day finding your footing i you know i i the i mean the first thing that jumps to mind talking about this and i don't know if this is true but like i seem to remember just you know you know like the the analogy i gave about cramming for a test when you come in in the morning you know and and you you tear through the newspapers it was very strange in that during that period you would come in and you would tear through the newspapers and it would be nothing but news you couldn't joke about you know like yeah and and so i remember us you know i before i was talking about how the the the balance between topical humor and evergreen humor i remember during that period it was just like you couldn't make topical jokes because it was just grim and and like i remember it's just like i think at one point like doing a top 10 list about the jolly green giant it was silly and it won't hurt anyone's feelings or make people cry um yes i remember that being an odd time i i i was not a huge fan of george w bush even in the days after uh 9 11.

so i i kind of very quickly wanted to get back on and and making jokes about the administration criticizing the administration dave was kind of wary about that like we need to we need to hang back and so yeah yeah and so that went in my memory it went a couple months and then i remember there was a weekend in i want to say december or january where the president um had bruises he had abrasions on his face and it was it was because the president uh choked on a pretzel and fell down and hit his head on a table and bruised his cheek and and thank you god i remember fine again at that point dave kind of nodded went yeah okay i guess we can make fun of this guy again like i think i think superman has lost his cape by uh oh that's tremendous i wanted to pretend he's this wartime uh president uh yeah defining moment of the late show uh and its tone okay we can go and do this again um there's a there's a beautiful moment of normalcy and again yeah the great moments in presidential history i mean they wrote themselves uh in many ways but you guys were able to leverage them so beautifully like everything in that segment there i love that segment um and i love the editing i've always loved the editing of of of dave's stuff the quick edits you know uh the the the the the fraction of a jingle and then it's gone and then it's like like i just love that that style how quick it was and and uh uh what a what what a great what a great thing that you were a part of that's dave i mean that's something that i've learned that i've carried with me and and i think it's really true is dave i mean his note on almost everything was short or short or short or short like like he really and i would watch and so like it would it would be frustrating at times because i would like like when i would do those remotes where i would go someplace for three days and shoot a piece and then like you know there'd be like a lot of jokes that i would want in there and i would ideally i would want like a big piece but dave was always and i would watch other shows and their remotes would be like seven or eight minutes you know right and i would be like oh my gosh i want that kind of real estate but dave was always like no the remote should be three minutes three and a half minutes and like and like i remember like you know i would hand in like you know a five minute cut of the piece and i would get word back like it's fine but it needs to be three and a half minutes cut whatever you want like if there's there's no bad joke here necessarily that i want out it's just more i want it short and like and and i i don't think i was there i i don't remember but like i i have a memory of dave at a rehearsal and there was some watching he was watching some piece where it was kind of um it was a joke where i'm doing a lousy job to explain this but it was basically the joke hit the premise and then it kind of it just furthered it was just there was a joke and then another example of hitting the same premise and another little redundancy all fine jokes but like dave was watching it and he just went you know it's you know it doesn't get funnier you know and like that's very true like the jokes might be fine but you've already had the great version of that joke the first time the audience has already got like it's not going to get funnier now it's like yeah let your losses take your win take your laugh and end the piece there you know get the drum one time that's all you need to do yeah yeah um i love that i love this i love this insight that you're bringing me um it's funny you know at the beginning of these things i get really like almost i get fanboy i totally totally do and then the discussion starts and and uh the insights that you're providing here tommy are tremendous i'm so grateful for this here um you you talked a little bit about uh this in in our last um few paragraphs there the idea of uh things that were were written and then cast aside not necessarily because they were bad right uh this is really putting you on the spot but i have always wanted this ever since i was in in high school reading about this stuff you know i nerded out about this stuff and i always wondered like the stuff that ends up on the cutting room floor uh for whatever reason um this is really putting you on the spot and there might be nothing because it seems like you just almost can't have nostalgia or a memory of things or whatever because it's just so fast and you got to stay current yeah were there any moments that you guys either shot something or you wrote something or uh and it was it was almost there but then now now we cast it aside were there any that you were like god damn i wish i wish we could have had that one in the show that's a great question um i mean like honestly like dave i would i would say like your your success rate generally like for a writer even a good writer was about 10 i would think you know for like you know every one thing you get on nine things are getting shot down it ain't baseball it's less than baseball so like that so that very quickly you kind of lose that you you understand that that's the gig and there's no taking anything personal in this game yeah and you develop a callous and you and so so it's funny like when you mention the joke that springs to mind i now realize is from one of my first weeks as a writer and it's probably because i hadn't developed that callous yet and so that's fascinating and and i remember it was there was a top 10 we did there was there was an you know a news story that some companies some part assume a pharmaceutical company had developed basically prozac for dogs sure and and so we did a top 10 list of top 10 depressing thoughts your dog has and so all the jokes are from the perspective of a dog you know depressing thoughts your dog has and i had one that i thought uh was just such a i thought you know i don't know i thought it was a smart joke and you know didn't hurt anybody and i i it frustrated me that it that they didn't pick it but it was um it was okay pressing thoughts your dog has and it was i'm turning 40 this year and 41 and 42 and 44.

you know who doesn't love a dog age seven years it's seven oh my god that's fantastic that is very clever and then another thing that i another thing i shot over weeks i had this thing called late show the movie which then i i saw later kimmel did kind of a similar thing but it was as big stars would come through for their interviews i would grab them before the show and it was basically i had this trailer for a fake late show movie that had like julia roberts you know just every tom hanks jason bateman all these you know star-studded and and uh for whatever reason i don't know dave dave just saw it and then was like i don't know you know just kind of queasiness about the idea of you know a late show movie like who were we pretending that you know and i was like ah wow not many other hosts would have turned down kind of that amount i was i was gonna i was gonna say um because the next question i have is is is learning to write dave's self-deprecating voice and things like that and i feel like him kind of being uh standoffish about that has to do with the fact that you know i i see that being a really funny late show type joke and then you know finishing off with you know and david letterman and then having a picture like yeah yeah yeah you know a punch line that leads to self-deprecation almost i i get that yeah that seems to me it's so crazy talking to you because you do talk in the voice of something that i've watched forever it's so interesting uh i don't know if anybody's ever said that to you or not maybe i'm maybe i'm not i am nuts but no no no really god damn you've got that sensibility there did it take a long time for you to learn to write in dave's voice or sensibility and was it conscious or was it just being in the environment it just had to show up yeah it but personally like i could see that being hard for a lot of people and and there would you would see it a lot with a lot of new writers because i mean it's crazy the amount of like the amount of sort of like trap doors there are in dave's mind like reasons he will have to kill a piece and just like these little landmines that writers will put in their piece that they don't even realize that it's you know it's you know uh it's gonna be a reason for dave to be like oh no we're not doing that you know and uh so i think just yeah i had i had been around you know for several years before i even became a writer and so i think i had a pretty good sensibility you know not 100 obviously but but like had a pretty good sense of what he would do what he wouldn't do and and yeah i don't want to go too far into inside baseball with this but but i'm going to ask the question anyway um are there any of those landmines that you can kind of talk about like that are that are fairly you know generic or or just basic you know don't talk about this because of or don't ever talk about this uh you know it's right it's a personal life thing or or something like that like um that's a that's a great question i don't know if i have anything loaded up but yeah there would be um and also i'm going to reverse myself now i remember hillary hillary clinton telling a story once when like in 92 when you know she when bill was running for president and kind of the moment when she realized her life had changed um she asked somebody for a dr pepper and they got her dr pepper and then she was like the rest of the campaign everywhere she went every hotel room there was just dr pepper there were dr peppers there were dr peppers and so i always would check myself like some i would always wonder like some of the rules we have about dave how many of those are things that we've now made hard fast rules because he said it once you know and maybe that particular thing and we've tried to universalize it you know uh you know i always wonder you know sometimes did we go too far with that like hamstringing ourselves yeah like oh we better not do this because dave doesn't like that unnecessary boundaries because you didn't like it one time or whatever yeah and you guys made it into an institutional uh rule oh that's interesting yeah huh i don't know um no that's that's i can tell another story yes oh my god as many as you want this is this is this doesn't involve dave but it kind of made me i was reminded of it with the dr pepper story and kind of the best version of that kind of power of celebrity um there was a guy who was an intern at the show who then later did uh an internship at skywalker ranch which is where they do the star wars films sure is so he was an intern there when i think they were doing one of the prequels wow and so george lucas comes into this conference room where they're having a meeting and there's a big conference room table and on one wall is a window into the next room where they're building you know droids or whatever you know they're building some sort of you know star wars creature yeah so george lucas is talking in the conference room and out of the corner of his eyes he's keeping a view of what's going on with the building in the next room and then he sees that they're kind of going down the wrong path and how they're building things so he goes excuse me he gets up he walks towards the wall and he has to you know he has to head out the door and take two steps and walk in the other door to get into the next room where the window is looking yeah and as he's doing that uh he just under his breath said oh it would have been nice if there was a door here so the next day he's in the conference room and he walks in and he sees that now there is a door there in the conference room and he went did you guys put a door here just because i mumbled that and they were like yes and he goes don't do that kind of stuff i was just i was just talking out loud do not do that kind of stuff and they were like okay he comes in the next day he looks there's no door they've removed the door now he was like stop stop stop me it was like midas trying to stop making things turn gold you know like oh my god that is um i'm a huge star wars fan like i you know i don't know that i can go as deep on star wars i can with letterman's stuff but but i can go deep and that is one of the best uh showbiz kind of example stories i've ever heard of something like that that exactly it's the fact that it went back again that's the funniest like time is what makes it the charge oh without a doubt yeah god i want to uh oh the right okay i want to talk about the render strike because again again there's a bunch of things that i'm piling in here in case it is the only opportunity i ever get to speak with you and then anything else from here is cake um you would have seen two writer strikes or just one i guess just the one just one um that was a real interesting time in in in comedy um i saw a group of you i don't know if you were on the panel or not but there was a panel that was done during the writer's strike where a few of you were uh on a stage talking about it somebody made it made a joke like how does it feel like being able to use david letterman as your personal sock puppet something like that um uh the writer's strike was a very interesting time and it was interesting in the fact that you guys ended up getting a separate deal than everybody else yeah um could you talk about the writer strike any uh memories that pile up as i as i say those uh clumsily put together words uh the words were lovely um i was uh i uh i guess i didn't understand the responsibilities of a union uh when the strike was first announced i was like because you know you're on this hamster wheel at the late show and then suddenly it was like oh a strike for an indefinite amount of time and i you know part of me was kind of like oh nice you know i get to sleep in and um i'm not allowed to write i'm not allowed exactly so i was kind of thrilled but then i was told by the union that that no we have to we have to go march and so suddenly you're not getting paid but you have to go out every day and stand in the cold and march and again it should have occurred to me that yes this is this is this is the responsibility of a union and and this is where all the good things come from a union um but the thing i want the reason i mention it is the first day of the strike the march was at 30 rock and it was the first day of the strike and so a lot of media was there and just all a lot of t you know a lot of stars who have writing credits were there also marching and you know and you know getting their picture taken in in the in the paper that first day day two and subsequent days no more celebrities you know no more celebrities except seth meyers there was never a day where i was marching and seth meyers wasn't there and i was so impressed by and i just wanted to give him a little shout out that that you know he was and he was on-air talent and yet he was he was plugging away every day on our talent but a writer before that though right yeah like always a diehard writer like yeah and so many this is a a great question for you now that people have seen you and heard you uh for 50 minutes or so um you know a lot of writers uh start writing dave himself you know uh tom dreams talked about this he wanted to you know when dave jumped in the truck and moved out to hollywood yeah the aspirations of of of of getting on the tonight show sure but at the end of the day realistically i want to be a writer gary shanley writer and then turned into performers uh seth meyers i think another good example of that just now that you mentioned um you clearly have uh the chops or the uh the personality where you could be a performer you're witty you've got you've got some cleverness to all that kind of stuff a brilliant writer um clearly you've got tenacity to be able to work there as long as you did uh have you ever thought about getting in front of the camera i i only in retrospect and and i regret that i didn't do it like i i would do is it too late i mean god man i mean it doesn't look like it's too late i think um but no but like i would i would occasionally do pieces on the show and i and like and you know only in retrospect now i think about how like you know it it's that thing you hear performers all the time where i would get very nervous beforehand but then once it was once it was going on it was like the happiest i've ever been and just and it just felt very freeing and like i've heard actors and stuff talk that way and like that's why i decided to become an actor and now in my old age i'm like oh wow maybe i should have pursued that avenue um but i guess i guess i kind of always like the idea of writing and just having some time and some care and and really you know being able to plan things out a little to polish it up and yeah and whatnot uh well you know you clearly have that delivery we didn't do any pre-interview really before this thing i'm just saying that as a organic reaction to our back and forth here um you know if ever you decide to uh to do a podcast or something like that anything like that you got a subscriber right here you're very happy when it comes to that thank you no no no of course um talk about remotes uh there's one in particular that came up you used to write for alan coulter did you ever read any of alan calder's remotes oh like the the or not remotes but like uh like sketches or yeah yeah i would write i would write i would write yes some sketches for alan and um yeah the i mean the thing that jumps out about alan is going back to the thing i said earlier about you know biff is who he is and rupert is who he is and the show like to its credit had a very kind of amateur hour quality to it you know like we we weren't slick professionals which was great and charming in its way sometimes as a writer it was a little frustrating that you know you couldn't give like a big soliloquy to rupert you know like um he would love that by the way but i would say that except for alan yeah anything you threw it allen he could do it he would elevate it he would make it better and just like he was just he was such a gift to the writing staff like it it was just it i just loved his talent and and being able to like give him a script and have him make it five times better um yeah he's an incredible absolutely was a pleasure right for alan i could imagine it was um i'm gonna ask you on the spot here if it wasn't if it wasn't you i'm gonna ask if you know who wrote it uh because i definitely want to talk to them my very favorite allen culture moment of all time was a video package that you guys did it didn't start with a video package it started with him on stage and randomly at some point he looks at dave and goes hey dave and yes allen and it cuts to alan and he's wearing a sailor suit okay he goes he goes uh aren't we gonna do the aren't we gonna do my sailor sketch and he's like i'm sorry allen i'm sorry allen uh we don't have time to do your sailor sketch and allen looks up and he leaves despondent and then the video package starts and it's him descending into an apocalypse now style horror the horror white rabbit is playing by jefferson airplane he breaks the glass and in the blood and he puts oh it was my favorite moment by far did you write that i did i don't think i did uh uh might get if if i had to put money on it um i would say that was probably uh carter bayes and craig thomas okay uh they they they often uh uh captured uh allen's descent into madness in a really nice way so i would i would i would hazard a guess that was them okay well uh shout out to those guys and uh hey i'm you know i'll get you my digits boys let's let's okay yeah um you know i i don't wanna i really wanna be careful with your time here uh what are you working on right now like i mean i've read a quote somewhere i actually it might have been from ian's podcast now i think about it where uh you know you worked for the late show for a long time and then you've been searching for jobs ever since or something like that yeah tongue-in-cheek um obviously working with straham and all that you've worked with larry one more oh i gotta ask you about this you helped write for the president the the windows correspondence dinner i not much i okay you're credited at it and then so i saw that i'm like oh this is this is cool yeah i mean i i i like helped a teeny amount but it was it was it was more i was i was the head writer at the time at the one more show so i was kind of tied up just with the show yeah so like i i i went to a couple like we had a couple meetings like to go over stuff like at night after the show but uh uh uh robin petey uh who's a great performer and um uh she was kind of the go-to writer for the correspondence thing yeah okay fair enough i just i saw that and i was like wow what a what a thing to be involved in even even even on the surface that's a really cool that's a that's a cool thing that some of your stuff has gotten into a a very exclusive room there that's all right yeah um i always wish dave would have hosted that uh that event that was always something i i as a fan wanted to see um so so what are you working on now well i i i have kids now and i i'm i'm less uh interested in the kind of late night world which is a grind and so i've kind of been trying the past couple years to like kind of develop a couple different sitcom ideas um to varying degrees of success so yeah so uh kind of writing writing scripts good for you um are you doing a lot of pitch meetings and things like that uh some you know which i'm a a you know is an art that i a skill that i do not have uh you know there's uh yeah people in la who do that kind of stuff a lot better than i i'm trying yeah oh that's cool man well i just i appreciate you so much for opening up uh your time to be part of this uh we want to build something that that really is kind of a living museum um an archive of again i say it like a broken record of the greatest body of broadcasting work in history you are a major major major part of that tommy um before we before we take her home are there any highlight moments and if you're like the rest of the staff that i've talked to you guys are you're terrible at at taking compliments and you're not very good at self-promotion that kind of thing um that seems to be a family trait but i'm gonna ask is there something that jumps out at you a moment that you're really proud of a couple moments that are really proud of that i will mention this one because you like star wars okay this is this jump to mine um uh bill clinton was a guest on our show one night and so before he goes on for his guest segment he's in an area that we call the airlock which is just like it's this little room right backstage where the guests where some of the staff hangs out and where um the guest waits right before they go on so right before clinton's segment dave's doing the top 10 list that i forget that the topic but it was it was a topic that involved star wars okay and so i had a joke that mentioned chewbacca and so dave does the joke and there's a monitor in the room and and you know people in the room are laughing and clinton turns to everybody in the room looking confused and said now who's chewbacca i i i won kind of like how i inadvertently got bill clinton to say chewbacca but i also i also find this it's it's a question that's plagued me now for years because we know what a liar clinton is i find it i find it hard to believe oh my god that bill clinton didn't know who chewbacca was because when star wars came out in 1977 he wasn't president he was like yeah you know maybe i i don't know attorney general in arkansas like the guy would have been aware i think he likes to put on the aura that he's this world statesman he doesn't have time for chewbacca sure but i think he was of an age where surely he he he was familiar with chewbacca and the guy does crossword puzzles and and so i don't know that's just you know i would love to really grill him on that but there's another element to that could be part of it he also bill clinton has this awe shucks kind of charisma that uh to me and i mean no no offense to any of the clinton people who might ever hear this uh that might be a little bit a little bit what dave naturally has yeah um kind of the r shocks the awesomes yeah that that that that that that folksy kind of a i think clinton does a really good job of flipping that switch sometimes and turning it on and the chewbacca thing it feels like oh this would be a fun thing to say you know and yeah um that's a delightful memory um god damn i cannot wait to share more of these uh with you at another time um is there anything okay so this is your first uh time on the letterman podcast uh we are um you know very uh you know humble in what we're doing right now and it's it's it's it's a studio that's in my basement that's about to be retrofitted and we're gonna do some really cool things with this um any advice for me here advice no none you're you're doing great this is this has been a pleasure you keep a nice smooth interview i i i think i think your space looks great and the fact that you're going to make it even more beautiful i think is just it's dazzling it's incredible you're doing great they ain't seen nothing yet i've got uh one way to wrap it up this is the way we wrap it up with everybody uh dave obviously doing the long form now my next guest we talk about letterman with all of the phases of what he has done with um you know equal adoration because different folk different strokes for different folks uh now that he's doing the long form if there were three people that you would like to see dave have on my next guest needs no introduction who would those people be um tarantino oh what a great answer just because i think tarantino does a great interview but but then also dave and tarantino had trouble back in the day and so remember yeah i would like i would like to hear uh an airing of that yeah um you know i always enjoy dave and tom hanks i think that's always a great interview i don't know oh oh that's like hey there's a good answer too yeah i love it tom hanks springsteen and tarantino that's fantastic uh from the mouth of tommy ruprecht right here you've heard it on the letterman podcast that is another episode i just i love them they go so fast but it is so much fun going back and celebrating all of this work that uh the entire team that tommy and the entire team did uh that was that was thrown down because they had a show the next day our job to pick up those pieces i got thrown down unearth them shine them back up again and talk about them tommy you are fantastic thank you so much for being on the show today pleasure let's well i don't know it was definitely my pleasure if it was yours as well that's a a massive massive bonus that is another episode of the letterman podcast thank you very much for tuning in this is the only time i'm going to ask this like share subscribe in whatever order you want we would love that we are a little engine that could and we really want to go some places once again the hello deli our only sponsor the show is brought to you in part by the hello deli hello deli dot com for all your late show with david letterman stuff and if you go down there have a paul shaffer sandwich tell them what's on mike thank you very much um and we'll see you in the next episode thank you and good night overcoat and underpants