Hugh Fink Listened To David Letterman’s Radio Show When He Was A Kid Then Performed On Late Show 4 Times

hey this is Gabe abson and you're watching the Letterman podcast welcome once again to the Letterman podcast my name is Mike Chisum I love tonight's episode oh my goodness is it good uh Hugh think Hugh think is a uh well a man of many trades uh in the creative Endeavor that is comedy um first off I didn't realize this started off as a broadcaster had no idea that was the case before before the show started what I did know is that he was a stand-up comedian for a long time uh that did a lot of cool things and then evolved his career onto the behind the scenes um having written for some of the most prolific people and tangentially connected to David Letterman um people that there are nor McDonald being one of them uh Craig Ferguson being another one uh but at the same time he also had four shots as a standup on Late Show with David Letterman uh Hugh grew up in Indiana and um as you'll hear very early on the episode uh there's a very cool story We we've had a lot of folks asking if there are people who have any connection to Dave's radio career before he became the weatherman and a surprising story comes forth right at the beginning of this episode with Hugh and then we are off to the races Fast Friends um lots of very cool uh tangental connections he worked for Saturday Night Live for a long time um was connected connected to David Spade um came up uh you know as an improv comic and just a lot of fun now and now after all these years doing all the cool things that he has done including written for major award shows and and and and television shows and late night shows and comics and um all of the above is also now a Harvard Professor so you can go to hf.com if if if he provides private coaching um so you could go to Harvard and you could take his sketch writing class um or you can go to huf.com and if you want somebody who has been in the business for a long time has an incredible width and breadth of experience uh and and if you're are comedy if you're a comedy person and you want to sharpen up your game uh H is doing that and it's cool a lot of these people that are connected to to Dave and Company's uh projects whether it is directly or tangent directly like Gabe abson Gabe abson uh you know he he works with a lot of stand-ups and doeses stand-up workshops um you know Steve O'Donnell head former head writer the legendary former head writer teaching at NYU and and and now uh you know talking to Hugh about this at Harvard doing this um what an amazing story I uh you know I let's get right to it here uh the Letterman podcast has one sponsor one sponsor only that is hello- deli.com Rupert may not own the deli anymore but he certainly does have hellodd deli.com your only place that you can get L show with David Letterman official L show with David Letterman mugs and shirts and hats and all sorts of fun stuff packed With Love by Rupert G himself uh Rupert has also Rupert and Irene right now have also said to say hi to everybody and they appreciate everybody who's been giving well wishing wondering how Rupert's doing since he sold the Delhi we got some videos that we're going to be putting out here soon but um without further Ado I am so pleased to uh present this episode of the Letterman podcast featuring our very special guest today Hugh thinkink Hugh I am so excited that you're here as uh as another uh late night host that I adore Conan O'Brien loves to say there's so much to talk about and with you um there really really is in from a comedy perspective in your career there is so much to talk about but of course this is the Letterman podcast so we have it with a bit of a letterman slant um I just want to say first off before we get going here congratulations on the career that you've had you've had so many awesome moments uh dream come true moments I'm certain for a boy who grew up in Indiana uh and that's where I want to start um you grew up in Indiana and of the other folks there's a There's a comic friend of mine his name is Trent Ma I'll give him a shout out here uh right off the top he's from Indiana and and and as he and I sort of connected I asked him growing up in Indiana you know I'm a Canadian and whenever one of our favorite Sons would go down south and have success um in in the US we would all vicariously live through that a little bit in growing up in Indiana having the comedy slant that you have was David Letterman that guy for you he totally was and particularly because I had a what one could call a personal SL professional relationship with him when I was in seventh grade because Dave Letterman hosted a call-in radio show on W NTS in Indianapolis which by the way nobody listened to except retired senior citizens crazy people teenage boys like me who discovered him and it was unlike a lot of popular Colin shows you have to dial the phone 50 times just to get through this show was so unpopular that I could pretty much at will get through to Dave anytime I wanted okay so he was brilliantly funny then and I discovered him but instead of me just calling him up as myself I came up with all these recurring characters I would do voices and my friends would all listen on the radio at home and uh hear me talking to Dave Letterman that is fantastic um we'll give a quick plug for Jason zinman's book it's I talk about Bill Carter's book on here a lot I talk about Scott Ryan's book The Last Seas of Letterman a lot on this show I love them all I love them all um they're all like little kids they're fantastic but they all are different from each other in particular Jason's book does go into Dave you know Dave is a he's not a standup he's a broadcaster that learned the discipline of standup and and um it wasn't just the weatherman thing and that's where a lot of folks think that his broadcasting began working for that television station being the uh the weekend weatherman no he had a lot of radio stuff from his college days and moving forward as well and was a bit of a ravel Rouser he was a Mischief maker uh during those times as well growing up seventh grade what kind of a DJ or an on-air personality I guess would be a better uh way of describing it was Dave at that point he was a fish out of water because he was super glib and sarcastic but you know the ho D and I are proudly from people are not sarcastic and glib there they're very straightforward yeah so I felt a comedic kinship to him immediately because when I listen to him I'm like oh my God he's completely uh poking fun at these people sometimes poking fun at the station poking fun at Indiana but listeners weren't necessarily picking up on it I was picking up on it so I immediately loved him for that okay so this is me and school or Junior High uh where we would go around and and and the it was like being part of a secret Club that's what late night was when when um you know the early incarnation of late night you know you'd go through school and you You' kind of Nod to the guy the guy walking past you where you both saw late night the night before and there was something awesome that happened you were part of a secret club that was already uh one of Dave's kind of calling cards early on if you know you know and if you don't if it goes right over your head so be it uh early on safe to say safe to say and I should add that my parents were not crazy about the amount of time I was spending coming home from school and listening to David Letterman in fact it got to the point where you know was before cell phones the phone was attached to the wall yeah but it had a long cord so I would go into a closet with the phone so my mom couldn't hear me making these calls to Letterman but occasionally she'd see the cord stretched across the kitchen and go what the hell are you calling that radio show again and I'd have to hang up oh that's amazing and uh by the way Jay Leno stealing your moves okay there we go um do you remember any of the things any of the interactions that you you said to him did you make him laugh ever was he in on the joke like was he that guy did he know who you were uh after a certain amount of time or was it always just he was just uh you know encountering each situation and dealing with it at the time I think it was the lad Mike because my voices were pretty good there was no way that he knew I was some 14year old so the one that I remember the most was my friends love the most was I did sort of an old grandma Yeah crotchy Grandma voice it's of course my voice has changed but sure I would call up and go like hello Dave go yes and I go I'm calling because I'm being overrun by Chipmunks they're eating me out of house and home and he being D would go oh well that's terrible you know you just need to figure out a ways to get rid of them and I go well I'm calling the Exterminator I want them dead and they would go oh no no ma'am don't kill them so and I would sometimes go like nothing would make me happier than seeing 12 dead Chipmunks in right crawl space and Dave would go you know Grandma that's not a nice thing to say at all so he would sort of have fun taking me on I don't think he knew it was a bit that's fantastic that's beautiful well let's see if we can make that happen now that would be great if we could make that happen Okay so uh you know fast forward a little bit then we'll rewind again um we are able we have skip technology in this podcast so we'll do that uh fast forward a little bit you're four times on Late Show um in my mind even though your your your hunks were clearly hunks from your standup routines they were very very much in Dave's sensibility and I'm sure Eddie had something to do with that I can't wait to get to all of that but in the interactions that one of the interactions you certainly were down in the chair beside Dave as he's doing the final you know uh sign off for the show you're sitting beside him um did that ever come up I know he famously doesn't talk to the people beside the chair sometimes and things did it come up that you ever called it to the radio show here's the story about that Mike here's an exclusive for you is all right we'll take it when I was at NYU as a college student and Dave was announced as the new host of NBC's uh late night yeah Late Show right late night y I was brave enough because I had my own radio show at that point at wnyu in New York and it was a comedy show I wrote him a personal note and requested a meeting at nbc3 Rock Y and his people got back to me and said Dave will meet with you right the only thing was I hadn't thought about was what was I going to say to him because he was already my comedic hero I was already pursuing comedy in college but I wasn't yet career-minded enough to sort of Say Hey I want a job on your show that's what I should have said so we sat down and he I'll be honest he was very intimidating yeah a tall guy and he doesn't joke around and he was under a lot of pressure about to launch this brand new network show he's meeting with a 14-year-old kid he doesn't know who the hell I am he doesn't so we sit down and he says to me I'm David letman what can I do for you and of course that was a perfectly professional thing for him to say but I was just so stunned I said well Dave I I just a huge admirer of your comedy and you know when I was a kid growing up in Indiana I used to call into W NTS and he he immediately like said those were some of the worst days of my career I didn't like them at all like like he completely yep was not oh my God yeah but he did say what did you do when you'd call in which gave me the open door sort of like you just asking me y I gave him a couple examples and the truth is he goes are you sure it was me that you called he had no memory of it at all and then he felt bad and he said well I'm sorry that I don't recall that I'm sure were funny but um I hated every minute of that job yeah and that was such a lesson to me that I worship this guy for what a brilliantly funny guy he was on the show yeah he didn't like doing the show yep how would I know that well okay so that brings up a whole bunch of other things and it makes me wonder because I mean in zinman's book he talked about clashes that he would have whether it was at the college station or or whatever he talks about clashes he would have with management and and and and and you know he would mess with format and do some of these things these mischievous things um you know on air and and and but later on you know uh talking about you know what his life was as he was doing the television show and he was many times said you know the only great hour I have you know I'm paraphrasing but the only great hour I have is the moment I'm actually doing the show and I wonder if when you know the microphone was was hot and he was working if there was was you know some sort of pleasure there or not um you know whereas all the rest of the vs around it was just absolutely terrible it's interesting uh very very cool that that that you did that so okay so you loved Letterman growing up uh you talk about going to college we hit the rewind button now and Skip back and go okay um came up with a guy by the name of Robert Smigel if I have it right right you and you and SM came up together Smigel and I I I didn't know him until we both were the co-winners of a colge comedy competition for all York City and they declared two winners at the end of the show Robert Smigel and me it was amazing now the difference is I came on stage as Hugh Fink and I was a you know 19yearold kid and Y I did early incantations of stuff in my stand Robert Smigel standup was playing an Orthodox Jewish rabby and he came on stage wearing a rabinal costume I couldn't even tell you what the jokes were but he did sort of a Old Eastern European Jewish accent that's pretty ballsy you know yeah but he and I won the competition so then I became familiar with him and thought he was funny and I used him on my radio show to do some voices this is very cool so um I I like you know I you added another dimension to this that I wasn't aware of um you know there's the comedian there is the uh comedy writer and I I certainly want to talk about that but you also have that broadcaster part of you as well and it's it's it's an interesting uh Alchemy when those three things can come together um and and uh you know only a few people kind of have all of those things it's very interesting do you uh do you ever miss doing the radio show do you enjoy it like have you thought about like this here there's a lot of the similarities that get scratched Alex Bennett friend of mine uh big radio guy from New York um you know says to say hi by the way um you know even to this he's in his 80s now and he does stuff over the ones and zeros now to kind of scratch that itch a little bit did you enjoy doing the radio thing or was it like yeah this is close to what I want to be but what I really want to be is that and and you know I love doing the radio thing I really did I I got the sense though when I was in college and out of college that other than Letterman it was like a complete anomaly and then later Howard Stern maybe yeah there was such little room for Renegade comedically sort of um uh underground subversive subversive people radio does not like subversiveness because it's all about selling airtime right and um for a while I was lobbing hard to get my own comedy radio show at the top AM station in Indianapolis yeah it's a station that Dave was never on but it was the top station and I had a great demo tape of all the comedy stuff from my own Radio Show in college and you know what they were intrigued they thought it was funny and well produced but they wouldn't pull the trigger oh man and so to answer your question I do love radio and I do miss the fact that I never really had major opportunities compared to my standup and other things to do radio but I love it yeah I mean um I can tell you like like I'm I'm a financial planner uh in a broadcaster was inside of me and it and it has come out and through this Letterman thing is just I'm so grateful for it because again I talk about it in and the our our our our dozens of uh of of enthusiasts that are in our audience will hear they're tired of hearing me say this but I get so much joy doing what we're doing right now that to me feels like I'm in as creative say I'm in the flow it just feels exactly right the standup friends that I have that's how they feel when they're on stage whereas you know the stuff around it isn't necessarily their favorite thing but on stage it's like the gods have you know cleared the skies and it's one of the most open fun things ever um I could totally see you doing a podcast I don't know if that's something like with all the stories that you have and all of the adventures you've gone on I could totally see it you ever consider it I have so maybe that's a conversation we should have offline sure yes I I have considered it okay well that's cool that's cool so okay back then uh you know early on when you when the neuroplasticity is still the cement is still wet as they say you're getting all of these skills under your belt belt um you know broadcasting that sort of thing stand up at NYU uh you win this contest with Smigel um and then at that point is that where the stand-up comedy career begins um and by the way uh you know classical violin training it seems that you have um your parents must have been uh very excited the first time you pulled at least pulled the violin on stage they were excited but my dad was fond of saying well finally all those lessons paying for them paying off um but yes I would say winning that comedy competition at NYU did give me even more confidence to think about a career as a comedian even though at that point in where the art form was it was sort of unheard of to how do you think about a career as a standup comic right because you know the clubs and all that stuff were just starting yeah the road map uh not nearly as clear as it is today and I mean I have one of the things I want to talk to you about is certainly Stand Up Now versus standup then um you know the years that you were kind of cutting your teeth in the formative years I mean really at the end of the day it's one of those things where people look back on it and go man those were those were the the the golden years of standup in so many respects were you only in the New York scene um or did you end up moving over to California uh earlier than later actually Mike I was really part of the LA scene more so okay so Comedy Store uh improv improv you were the Improv improv guy okay TR be told I was at the comedy store for two years not doing that well and then Bud fredman the owner of the world famous improv saw me and love my act and I never looked back I switched to the Improv yep and stop performing at the swort that was back when the competition between those two clubs was so Fierce you could only work one or the other are these K the kenneson days or is it after the kenneson days it was the Kennison days okay so yeah oh my yeah that's Bonkers you know Letterman was not an improv guy he was a comedy store guy uh Seinfeld was an improv guy not a comedy store guy yeah so um with me I was at the comedy store for two years but I wasn't really getting much love and then Bud fredman saw me perform at the San Diego improv and he was very taken with me and I was smart enough to lie and tell him that I had just moved to LA and didn't work any clubs because I was afraid that if I said yeah I'm a regular at The Comedy Store it would spoil his excitement yeah uh before we go to the Improv and I have got many questions about that but but let's talk about you were regular at the comedy store so you passed Mitsy which Seinfeld which Seinfeld didn't do uh you know very very interesting so you actually did get past mity um very very cool you go over to the to uh The Improv who were some of the contemporaries that you had at that time who was in your class as people like to say at The Improv yeah so it would have been um David Spade Adam Sandler Rob Schneider like all three of those guys got hired at Saturday Night Live yeah yeah yeah absolutely and Smigel was Smigel there as well at that oh Smigel is not a standup like you said that's right yeah Smigel was never part of the standup scene so you just reconnected with him later at 30 Rock oh that so interesting it's pretty cool yeah it's really cool and and knowing that you met those three guys at that point um you know doing their thing I mean I I still the opening credits to funny people to Jud appow uh funny people I just I I I just want to see more of that stuff I want to see you guys screwing around back then trying things out it was just um it seemed if you were to compare the two The Improv in the store if you were to take those players and compare some of the other the store seems heavy and it seems so much lighter over over uh at The Improv it just seems like it's just more I don't know more fun I don't know if that's a a just an outsider looking in at at history reading books and stuff but it seems like it must have been a very fun time it was a super fun time I mean my feeling about that period between the clubs was that The Comedy Store had a much darker Vibe that's what I'm talking about I feel like it was because of drugs yep it because of mit's Personality um the way the club is constructed it looks like a strip club yeah honestly it looks like a stripper club yep whereas The Improv on Melos could be nothing but a comedy club small tiny room with a brick wall right um so yes I would agree that it was um more light but here's the biggest difference I feel like the taste of Bud Freeman and Mitsy Shore was very different back in those days and that the comedy store while there were great comedians if I had to say the difference it tended to be more theatrical more silly comedy and The Improv was more intellectual and more verbal and ironic that ironic that Dave's a comedy store guy and not an improv guy because comedy-wise he would have fit in better at The Improv um you know we talk a lot has been talked about with Jim mcau and and and going to the comedy that's what da that was the beacon for Dave to say okay I'm going to take the chance and move from Indiana out um I assume that there was a lot of that going on at the Improv as well though I mean The Comedy Store sure it's uh you know it's s of known for that but the Improv also known for that um were there a lot of shots that uh that you were there where there were um folks from various agencies and shows and things like that oh my God all the time I mean casting people from the studios top agents Dave's agent you probably read Marty kleene yep he came to to see me there and that was a big deal to get Marty Klein to come to the Improv to see me mcau was at the Improv every bit as much as The Comedy Store absolutely so oh no they they were both the clubs in LA and the clubs in the country at the time and then Zoe gets into the business which is which is interesting right um I don't know if Zoe was hanging out with you at that time or if she was in New York or if she was she was in New York I didn't Zoe until really she became a executive at Comedy Central television network in la oh that's way late okay interesting was at Letterman oh my God that's so interesting it's a it's a really it is a small world like even though it's blown up the way that it has the way that comedy has standup has it really is a small world but back then it really was a small world it TR exactly oh man that's so cool okay so you're at the Improv um with these guys uh David Spade obviously a huge part of your of of of of your career um in that regard but at the same time you're also um you're you're you're you're you're getting your chops when it comes to standup at that point um I I watched the uh the Dangerfield uh showcase that you did um how did that come about because I mean you know Ronnie Dangerfield you got to talk like that must have been just you must have been dumb struck to meet that guy and and and to be a part of that it was remarkable so yeah a comedian named Bob zayy okay who was um also known to book comedy clubs in the Southern California area at the time also destined to be a comedian with the name Bob zany I mean my God name yes but um somehow I don't know how this happened Bob zany and Rodney became friendly okay and Rodney started picking zany's brain about hey I want you to help me find the comedians for the next special and I don't know how this happened but zany was kind enough to recommend me so Rodney came to see me at a club on the west side of La called IGG comedy Cabaret that was it wasn't as prominent as The Improv at the comedy store but it was still you know pretty good club Y and it went great and being Rodney who he is I guess he said I gotta see him again so he came to see me again yep and I had another great set and sure enough he said I want to see him again and it it wasn't that he doubt I mean he loved my standup yeah but I think I was young and green and he simply wanted to make sure that I could hold my own consistently but after that third set he told me to my face you're G to be on my young comedian special on HBO how old are you at the time I was 31 and it's funny because that's the young comedians uh special but at the same time I mean the craft is such that you know you become an overnight success after you know 15 years of work kind of a thing it's one of those it's one of those things is was that at the time was that the biggest shot of your career it was but sadly Mike I was just a few years late and what I mean by that is his previous HBO specials yeah done at a time when there weren't nearly as many standup comedy shows on television so other than Johnny Carson to be on Rodney's special was so huge yeah this is true story for you comedy had become so common on TV that the night of my HBO Rodney DB special I was on Fox at the exact same time on another standup show kidding me oh man yeah but you're okay so that's astounding to me and and I believe there are no coincidences so that is very very that's extremely interesting but you're also painting a picture of when standup had its first kind of real boom this is when you know um Canadian but like A&E car Comedy Hour uh um you know I I just I I absolutely uh ate all that stuff up but it was it was everywhere it was it was really really blowing up at the time and so the dilution of Rodney special uh didn't give you kind of the impact that it might have a couple years before I got no and that was that was so kind of heartbreaking because a lot of people tried to tell me Hugh this is your break y like your career is going to change overnight and it didn't yeah I think a lot of the reason is again because there was too much standup out there yep a lot of people didn't even watch the special because they could watch stand up you know on other networks yeah I uh that's that's that's heartbreaking um but it's also historical at the same time it's also now were you also at this point writing or was standup your singular uh kind of uh focus at that time standup was pretty much my focus at that moment I mean had thoughts about oh I'd love to be a writer yeah but I had really put that together yet gotcha gotcha and I taken some acting classes so again it wasn't my passion acting but my feeling was I mean other people in the business were telling me you should act you should learn to act right I felt kind of why I have to do this were you in the race for okay yeah uh the up it's upfront season and I want to do a pilot I want to do you know was it because that was a huge part of the culture or at least a segment of the culture of stand up it was definitely a segment I wasn't someone who was you know being offered Pilots I certainly wasn't auditioning for major roles in Pilots right I did some auditions but I had peers their standup wasn't as good as mine but they were better actors and were definitely pushing that side of their careers more than me okay okay I gotta yeah um so that being said you're you're slogging it out you're uh on the road okay now you just dispar okay you're back I don't know what's happening here let's see I don't know it's like the Sun is setting that's what it is yeah doing its thing see if we could fix this here oh that's so great I'm keeping this in yeah absolutely keeping this in because I like yeah um I like I like the loose nature of the of the conversation everybody no pre-interview on this we just we're just going we're just we're just having fun talking here on this um okay so the Dangerfield special happens you're going um on the road all over the place like are you flying across the country all the time or are you but I had a rule which is that I never wanted to work more than two weeks in a row without coming back down light so I would one or two weeks gone then back okay back I was getting a lot of spots at the Hollywood improv so I was there you know three four five nights a week sometimes just working the muscle just going out there just getting her done um yeah no problem at all see if this helps at all didn't really help okay not really is that a live shot of oh there you go if you move there we go that's looking good oh much better yeah there we are um okay so we're into the early 90s now at this point here um and and uh David Spade did he get his uh his first look did Lauren come and look at him in California or or was it someone that called him over were you around at that point were you there the night he had his look I was not there the night he had his look I was there when he flew out to LA because he had just been cast in with Bobcat gold weight yeah and um what were those movies you probably remember the police academy not the police academy movies yeah yeah yeah yeah made out of nowhere got C he had no acting experience so there was a lot of Buzz about this short guy who looked like he was 17 years old David Spade so that's how I met him there's already tremendous Buzz about him yep um I'd say maybe a year later or something like that he got Saturday Night Live and I think Lauren probably saw him in LA but I'm not positive about that I know that Spade said he didn't do great he right he just did okay yeah but laen so smart he didn't care about crowd reaction right he was looking at him first of all he was hired as a writer performer so they weren't just thinking of him as a performer they could tell that he had a unique voice and what was jumped out so he goes uh he goes to New York and and um you know there's so many times where you hear kind of the dark side of comedy and things like that where people um you know they have material lifted or or or or or personas or ideas that are lifted that sort of a thing um this one here is one that has an extremely happy ending and and it's one of the things where you know David Spade goes a Saturday Night Live and and you you as I don't know if it's an encouraging friend I don't know if it's as somebody who you know wants to get a look uh you know in the attention of these people or if it's a combination of both but you are like supporting Dave and helping him from a material standpoint as he's there his first couple years fair to say that's that's a fair assessment that um we had a similar comedic Vibe yeah our material was different but we respected each other's acts a lot yeah and David sort of sought me out as someone who could potentially write jokes for him and I was thrilled to yeah because um he was skyrocketing his career um and so sort of it's an ideal thing that if you're friendly with someone but you also like their talent a lot that's sort of how it should be that's a great scenario right there well because you got Synergy on all levels at that point then right and you can kind of um connect and and and and I mean you know I remember that's my class by the way you know they say that your favorite El cast is the one that you had kind of in high school that's bang on me like I I worship Phil Hartman I worshiped those guys and then when you had the new kids come along so you still got Carvey and and and and some of these other people that were there uh Kevin nean and Phil Hartman and all that but then the new kids showed up in Sandler and Farley and Spade and rock and they all come at the same time and and I mean you know so many words have been written about uh the competitive nature uh at that show at that time I remember back in the day when David Spade was considered oh is he like a like like a mini Dana Carvey and a lot of people said that because they had similar sort of looks and and and Cadence perhaps um but the thing that put Spade in my viewpoint on the map was the Hollywood minute and the Hollywood minute was fantastic and brutal and cutting and hilarious and all of these things uh it was a weekend update spot where David Spade would just come on and it would be sort of a put on of of of the Entertainment News segment of a of a newscast or perhaps Entertainment Tonight and he would just eviscerate eviscerate celebrity um and as a letterman fan I'm sitting there going this is fantastic I love this he's taking the piss out of all these all these people you were a part of that and I mean I don't know how big a part it was that's my question like uh was that one of the major contributions that you did before you actually came to the show officially was that uh was that one of your number one Hallmark or calling cards that you did for space I would I would call it a small contribution in David wrote most of the jokes and a couple writers at SNL who were already at the show would help him but he did reach out to me and of course back then I would fax him jokes absolutely you're a faxer there we go and I did I did get some uh through on the air so that was thrilling so I think that I was just he really valued having someone who wasn't at the show because I wasn't caught up in the politics and the the competition right I was just more of a trusted comedian friend you were a gateway to the outside that he knew and trusted and loved ah okay so that was how the relationship sort of progressed I can remember um and this might be after you you were hired on uh but I can remember uh one of the jokes that he that he did it was about Robert Downey Jr's movie he he decided to go just like do a rapid fire section I think in in in in a Hollywood minute and it was you know a picture of the the movie poster for chaplain came up he's like chaplain more like klain and then he just moved to the next one I don't know if that was yours or not but I certainly that was not mine but that's of course you're doing a good job of explaining his style I'd say the height of my contribution to Hollywood minute was the most famous Hollywood minute um appearance he ever made but famous maybe for the wrong reason it was the Christmas show 1995 you can check it out okay that was the one where he did the Eddie Murphy joke there you go but here's what's crazy that's not close to the best joke in that Hollywood minute there's so many other jokes that to me are more memorable and more impactful and I wrote a lot of them oh so that's why I say that it was sort of my crowning achievement uh and then he came back after he left the show yep came back as a host yep and I wrote a good part of the jokes he did at his return and I think that was a really strong appearance as well and you were a staff WR you were you were on staff at that point as a writer by that point after he left uh came back for Black Sheep is that what uh maybe he came back for something could be right I'm gonna think it could have been black sheep or something after Black Sheep I forgot okay okay so so either way um this is this is an amazing time in comedy things are blowing up like crazy SNL is is is back on on on on the hot streak again for a while and then then it gets into the dark years again um interesting that you've seen a couple of a couple of those things but then there's another guy by the name of and this is where the Letterman uh enthusiasts will come back up and get excited about this and I mean I can't tell you how much I the the reverence I have for nor MacDonald I have so much reverence for that guy and and and I want to ask you about that but as you're doing this as you so you get hired on for Saturday Night Live um during these times you're still doing standup though still doing standup so at that point um you're going from LA to New York now you're you're you're relocating uh easy to become part of the uh the con you know because I went to New York University so I knew the city I'd already so unlike for a lot of people I was very comfortable in New York I knew the neighborhoods I was super excited and that really was not a hard transition for me and easy Gateway into the well now that you're SNL writer I mean you've you've been in the business for a long time the danger field special all of that so you've got Street credit at this point already anyway and obviously the SNL credit helped a lot but I'd like to think that when the clubs did have me I would deliver right absolutely but you got to get in the door you gotta be able to get on stage though so for them it was a bonus to have an SNL writer comedian so I didn't want to work all the time because you know I was kind of tired yeah physically from but I would do shows during my off weeks at SNL and sometimes on week Sunday nights sometimes yeah okay so at this point here's where the question's got to come in um did you enjoy what which part of the comedy muscle did you enjoy flexing more the writer or the performer at this point at a certain point I probably love the writing every bit as much if not more just because the thrill of coming up with an idea writing it getting on network television yeah was just incredible right y but I never gave up the standup obviously and I still love doing it I didn't miss the road that much because I'd done it for 10 years right right now I would I would occasionally take a road gig but not very often yeah because I need to but just performing at clubs in New York City and getting really good spots and um going over well I definitely love that I mean I can tell you the highlight of my standup live performing career was during those years yeah and you may have heard about this is when John Stewart asked me to open for him at Carnegie Hall this is on it's on the it's on the list right here absolutely okay so this is while you're writing for SNL you're opening for John Stewart at Carnegie Hall John Stewart at the time was not Jay Daily Show John he's uh I got oh it was it was okay so it would have been really early on then if that were the case ear it was early Daily Show he'd only did on The Daily Show for maybe one year okay okay and he does a deal at Carnegie and you're the opening act how did that how that happen have you heard of the Toyota Comedy Festival sponsored so it was a huge festival at the time so John was head obviously he was a well-known enough comedian to be Headland in Carnegie Hall as part of the festival yep and uh how did that how did it how did it happen at that point that you you got to be that or agent Jim Dixon yeah was standup yeah and to Jim's credit John didn't really know me but Jim Dixon said I know who we should have open for you this guy he's a stand up his materials good and he uses classical violin and his act it'd be so cool so they asked me to open for John and I the show was hosted by Allan King another Legend So Allan King who was probably you know then in his 7s um he MC he introduced me I did 20 minutes Y and then Alan King introduced John as the headliner unbelievable at this time would you have known Eddie bril barely okay so you're hardly even new BR at that point okay we may have like seen each other in the clubs yeah but not really knowing each other okay I gotcha um were you okay so let's go back to Letterman for a second were you working for 30 Rock when late night left uh when Letterman's crew left Conan took over and then they went to Late Show were you at 30 Rock at the time no I think I had just left SNL what what year did no that was that was 94 9394 in that time Carson 93 right oh um yes so no I'm sorry Conan started like a year or two before I joined SNL beforehand okay so so okay gotcha I gotta um yeah that makes okay yeah that makes sense totally yeah I'm I'm wrer he had been a writer at SNL a few years before me I was going to ask if you knew Conan as a writer I was going to ask if you okay there we go I did do Conan twice before I did my first Letterman yes and so I got to know Conan yeah and then Conan hosted SNL only once and I was a writer at the show then and we got along great and um I wrote a sketch for him so yeah so uh did Robert Smigel come back that week as well and and was he a part of oh my God that's a great question so you know Smigel is a brilliant writer but the writers at SNL who came after Robert were sort of the attitude of okay we don't really want Robert around because he's so dominating because he's the Iron Man so here's what happens is Conan O'Brien and I meet one on-one because Conan asked he said if any of you want to meet with me before I host SNL just come down to the to my office we're in the same building I'm the only writer who took him up on his offer unbelievable yeah only because I had you know that was my work ethic it's like Conan's offer to me so I met with him we had a great meeting and and Mike Conan O'Brien said so Hugh how do the writers feel about Smigel coming back to write for me are they talking about it and I just smiled said yeah yeah they're talking about it but as you can guess Smigel did come back yeah that week and had a major impact that week he wrote Conan O'Brien's monologue but I will give Robert a lot of credit between dress rehearsal and the live show of course they were deciding what sketches to cut Y and my sketch with Conan was on the bubble meaning some people thought it should be cut yeah and sple pushed for it ah and of course at that point I mean he's bringing a whole bunch of not just the idea of the Iron Man writer that can write an entire show but he's bringing also oh I like this one and it sways the influence totally because Lauren Michaels has great respect for for Smigel yeah if Smigel weighs in and goes no no Hugh sketch you gotta keep that one cut this other one did you guys had you guys connected at all before you started working with SNL again or was it kind of a kind of a hey look back I take it back okay when I I'd visit Spade when he was right at us before I worked on SNL was already a comedian so I connected with Smigel there oh there you go there you go and uh you know couple of kids from NYU doing good it just it's it's such a um let's get back to Norm for a second here um I I just the regard that I have for Norm McDonald I was just going back and forth a little bit with uh you know not to name drop or anything but Tom Green and Canadian right like like and Tom Green when he was coming up in Canada one of the guys he worshiped was nor McDonald nor McDonald was a guy that just you know and he worshiped Norm worshiped Dave like we all love Dave I just I adore Norm so much um I've had Daniel Kellis and and Steve O'Donnell and some other people who worked with with Norm on um how much how much did you work I know you wrote some of his Larry King stuff uh Curious very curious if you ever wrote any of his David Letterman uh stuff or not or if you were gone by that point but how much did you how how well did you know nor McDonald I knew him well not as a like we didn't socialize but we hung out a lot at Saturday Night Live right because his office The Weekend Update office was near my office yep as a comedian he likes comedians more than actors yeah so he would just make me feel welcome to come and like you know shoot the breeze with him and his two writers yeah so I did hang out with a lot but beyond my Larry Kings which of course I'm so proud of yeah I was headwriter and produced the espie awards one nor most famous appearances ever absolutely so I had some huge moments with Norm um you know we miss him every day he's a guy that just oh my gosh and the way that he went out and then you know H having shot a special to camera just doing this to camera I just uh there was no one like Norm McDonald again unique um and and and prolific and all of these amazing amazing things I love Norm so much did you know that at the time like did you did people like like he's he's known as a comedians comedian um but many time there's there's a lot of people who didn't kind of start seeing that till later on um did you see it early on with Norm I did see it early on in fact you know who was a big fan of his Rodney Dangerfield oh there we go and I remember specifically Rodney had a short-lived comedy club in New York in in La at Century City Mall and this was in the this is around the time I shot my young comedian special y so I'll never forget Rodney asked me to um come to a Friday night spot at his La Club well he booked Norm as well oh you're kidding I didn't know Norm well we had seen each other a few times but I always thought it funny and he crushed that night at Rodney's Club he did better than me and I could see Rodney was really fond of Norm oh that's fantastic and then you know what I was at live and Norm was still doing Weekend Update Rodney was promoting a movie much later in his career yeah and Norm had him on Weekend Update that's fantastic and you were there you were you were there when that happened I was there when that happened so you know Rodney was so thrilled and proud of me that now I was on Saturday Night Live and even though he had never necessarily booked Norm on the television show yeah obviously Norm worshiped him too and he so it was it was pretty cool reunion um when we talk about stuff like this here because you have this This brilliant comedy mind you clearly um you know have a have a historical mind for it as all the the medium that you're in like are there Pinch Me moments like these are moments that just are are just so incredible that you go back to the kid in Indiana did you ever think that it would become where there would be moments that you're reflecting about 20 years later about moments that are kind of really iconic in so many respects I appreciate you saying that you know I think honestly I've forgotten about how to enjoy those Pinch Me moments because career-wise one always has to think of like what's coming next yes and to quote it's one of my favorite quotes in Show Business is Bob Dylan yeah uh he said Nostalgia is death and I know that sounds harsh yeah but what take away from that mic is that if you spend too much energy just going over those Pinch Me moments and sub to things you'll sort of kill your own creative drive because you're basking in the glory of what you've already done yeah as opposed to focusing on what you could be doing or new moments to create so I think that's where I'm at is I when I reflect upon the career and some of these moments of course it brings back some incredible amazing encounters and highs and all that but I also have this weird feeling about but don't do it too much oh you're you're preaching to the choir on that like um you know it's funny I don't know if we'll ever get Dave on this show or not like he's aware and all that sort of stuff and and what not but I don't know that we'll ever get him on because of just simple the idea like he was just recently on Neil Brennan's podcast on blocks and and Neil went like hard in the paint going back to talking about the past and Leno and all that sort of stuff if I ever do have them on I want to talk about like I want to be very very Ginger I might ask about some comedy store stuff or whatever but I want to more talk about like the present and the future because clearly that's a dude who encompasses exactly what you're saying like exactly what you're saying um you know you don't don't spend too much time in the past because you're creating new things in the future and we've all known uh musical acts or bands that tour around and you may go see them for a nostalgic act but they haven't written anything new in 20 years and and they go and they play the hits and and and they're 20 years older and you know and I'm not saying that that's a bad thing it's not a judgment call at all but I certainly um admire the creative output that Mr Dylan has done in his entire uh run including some of the best stuff that he has done has been stuff that he's done lately Paul McCartney another great example of that um and and so I I you know the the the quote that you just said certainly does have weight but that's my job um and the whole reason why this show exists is because what you guys all did back in the day um and and and I say this to the uh to the writers especially of late night or late show that appear on this show um you know every single day you're in the mine and you're mining like diamonds and rubies and emeralds and you're getting them and there's these amazing things that we love for the moment and then you're just casting them aside because it's another show tomorrow night and you just keep on mining and this whole program here is meant to pick up some of these moments to pick up some of these diamonds um and and talk about them later on in life that's what that's what this show is about when it comes to that so thank you for for honoring that I want to get to the point now it feels like timeline wise we're pretty damn close to your first shot on Late Show it was uh it was summertime of of 01 was your first shot um was Eddie a big part of getting you on the show how did how did the first booking um happen Eddie was gigantic yeah I'll always give him all the credit in the world and I to this day you know and um Eddie saw me all I had to do was showcase once for him and we went out for Chinese food after the Showcase and he goes I'm putting you on the show where were you at the seller at the seller I was at standup New York okay stand up New York and and one thing I'm putting you on the show yeah and it was it was so Bittersweet of course more sweet than bitter because in my opinion Mike I should have been on that show three to five years before then yeah but the previous people never made it happen gotcha so then it just takes one person to come on board and and say yes did you know Eddie well by that point no did not okay so where did the connection happen he's he happened to see you that night or was it uh he I'm gonna say this he probably saw me another night and came up to me and goes you know Hugh I love your act you haven't done let himman I said no he's like man you know you you would do really well on it I'm going to set up having a showcase soon so I'm going to put you on the Showcase most of the material I've seen you do you talk about being from Indiana um I was wondering if if and I mean your sensibility the stuff you've done on the show are hunks from your act like it's it's which is which is how typically it is many times you know um and you don't seem to be the comic like a like a Chappelle or a burr who who who really did get a lot of exposure on Late Show but they had to significantly figure out what their hunk was going to be that was safe for TV you didn't seem to have to do that um you're kind of out of the box you seem to have a sensibility that would be perfect for that show uh was the fact that you're from Indiana a part of the was that ever part of the conversation I mean I think that Eddie did say Dave will love the fact and he said I've been telling him about once he booked me he started telling Dave about me yeah so by the time I did my first appearance Eddie was like Dave so excited to see you yeah um very I'll get to this part in a second here because I want to Revel in the first shot for a second here now you're at this point I think we've done a really good job painting the picture of where you are in your career seasoned seasoned had a whole bunch of cool happened like really good stuff happened in your career yet at the same time here you are at that point in your career appearing on the guy show who you called into His Radio Show when you're in the seventh grade was there Gra at that point was there an extra bit of like I mean you know you're hunk like like nothing like you can recite it like it's nothing I get it but like was there an extra bit of gravity was there nervousness was there or were you a Season Pro ready to go Mike it's a great question asking for the first one of a few times I didn't realize it there was nervousness and I think it's because how much he meant to me and inspiring me to go into comedy yeah and the fact that my journey was now taking me to his show yeah so I I didn't feel nervous until a few minutes before they called me out yeah I felt my hand like shaking and that never happens wow and again if you seen the appearance I'd like to think that no one knew that if you watched me on TV or in the audience no I didn't seem nervous but I was actually um I have a lot of pro wrers that are in my life uh just just are I have an interesting kind of background of things that I have done in my life and it's so interesting hearing um even pro wrestlers at the highest highest highest level they say if there's not a little degree of nervousness before you're about to go through that curtain um it's probably good to take the night off because you know you need to have a little bit of that that juice to get you through and that night you had a lot of that juice that's a good thing um you know by that point though you're so comfortable with television any had you had you been to the had Sullivan Theater to see Dave at that point had you ever been in the theater before I I'd been I don't even think I ever was at the NBC show I never went to it no yep yeah so uh going there you know you talk about Nostalgia and and it's it's you know when you're a performer like that and a creative like that not a bad idea to freeze things but at the end of the day you're in a pretty significant building um any of the gravity that hit you that night the building itself wasn't really attuned to it other than the fact that the true thing that I'm sure you've heard talk about it was freezing yes absolutely freezing fresh that's right right but um I wasn't really paying much attention to the theater I think I was so focused on my material did you have a separate segment producer other than Eddie or was Eddie your guy Eddie was my guy I remember the like the who would have been the voiceover person at the time I think calter was there at the time I it was alen he was nice like a couple the other people were nice to me in that regard yeah um yeah actually one of your spots uh it's coming back from commercial and you can actually see Eddie walking across the stage to go over to the other side of the stage because it's clear he just talked to you waiting in the wings and uh and and and so you know he's there right right for the last second um you go out there you do your you do your shot I think it was the first I think it was your first shot that you were on there in in in ' 01 I think it was July of 01 which is my next question's going to go uh after this one um you know so you do your shot it goes very well and I believe you end up on the couch beside or the chair beside Dave so Dave does the sign off I believe it was your first show that that was the case yeah and here's what you wouldn't have known and this is still one of my biggest frustrations is that he called me over to do a short interview after my set before the show ended it got cut a three or four minute segment with me yeah the problem is Mary Lou Henner went so overtime that they had to cut me oh so there's an actual interaction there an actual interaction I can even tell you what he said please do he he said Hugh that Chinese waiter bit is brilliant he goes will you do that again he had me do it again from just sitting down with them are you kidding me no oh that's fantastic one of my questions on here is okay you're a seasoned comedy guy you are like you know an upper echelon um Zar leader when it comes to Comedy when when it comes to this stuff you could give people advice that sort of thing could you do that joke today yes good okay I believe I could yeah I will say that it's possible that some audiences may not resp respond as well as I'm used to doing right for maybe the reasons you're thinking but I do believe I could do it today because because I feel like my premise is so benign I'm not saying I'm saying I had one Chinese waiter who was sarcastic it's not not a generalization about any ethnic group nope so that's why yes I think I could um and it's so it was so like you there you go that's actually a you're you're highlighting the reason why Dave would ask you to do it again because it was so benign it was just is he being sarcastic or not and it was just a really really clever uh take on on something that people would find familiar all the way back to well we've talked about this on the show like breakfast and Tiffany's Mickey roor doing what he did in that movie um yeah or Mickey Mickey Rooney I should say Mickey Ro that's a very oh man let's remake Breakfast at Tiffany's with Mickey roor there's there's an idea yeah there you go um no but but you think about that and you think okay the imitation of a of Chinese waiter but no wait a second so clever in in and again I'm I'm of the belief that if it's funny it goes and uh it was so so Dave got you to do that again at the chair that is very cool um the other thing to tell you about is that Eddie had said look no guarantee but Dave May really like you and he might call you over so think about what you want to do in terms of material or bits so because as you said I feel like I know Dave's sensibility so well y said Eddie I want to tell him a very quick story that it's not something my stand up but I think Dave would love it yeah here the story is that I would have said hey Dave you know the Indiana State Fair held annually in Indianapolis he'd go yeah of course I said well when I was a kid I went to it and there was a sign that said genuine Italian fried chicken I thought well that's kind of odd so being you know kid I went up to this woman and I go hey I have a question what's the difference between Italian fried chicken and regular American fried chicken and she goes well Italian Fried Chicken is very very good that's all she had clearly it was completely fake she didn't have an answer for how it was different don't you love marketing isn't marketing just great but I thought Dave loves that kind of stuff right just phony marketing no plan at all trying to you know fool the general public with stupid so I can't remember if I got to tell him but I know I want I told Eddie that's what I want him to ask me he I want him to go so I hear you used to go to the Indiana State Fair I thought there'd be a perfect segue absolutely perfect perfect layup for you to just you know or perfect set for you to spike um so you finished the first set and uh obviously it goes go ahead there something I should tell you that happened so I know a lot of people celebrities big stars Dave kind of gives them the cold shoulder and doesn't really talk them he could not have been warmer or nicer to me okay and this is extraordinary before my set before I went on he came over to me backstage and said Hugh I am so excited to have you on the show Eddie uh showed me maybe your he goes this is amazing and uh you're gonna be great so he did that then after the show ended he came and found me yeah that's rare you don't you don't hear that story very often at all you know what he did he apologized that I hadn't been on the show earlier you're see in fact you might even be Jaded by this point Jed honestly I'm a little Jed okay and he says this to you and there's no way that didn't Crush right through that diamond exterior that's there he's not stupid he's going why is this guy been around and he's never been on the show before yeah that's what I was hearing from him yeah that was of course such a validation yeah oh Hugh that makes my day I love I love hearing that that makes my day you know 20 years later it makes my day and it's that that's a really that's that's that's precious it's it's fantastic it's pretty remarkable and I have talked to my colleagues who've done the show and yeah I don't have any one to compare that story to that's fantastic um now you brought up something earlier that I want to bring up uh again right now in today's day and age and the part of the reason that um you know there's a guy that worked for Dave for a long time his name is Rick sheckman I bring him up as much as I possibly can I do this show because of Rick and Rick was the guy that he was kind of we he was my consiliary that's what we that's what we called him and and um you know one of the reasons that I would talk to Rick this is before the first Letterman podcast I would talk about and lament the fact that people have forgotten who Johnny Carson is and at the time Johnny Carson's the biggest star in the world period you know Sinatra might have a you know depending on the time frame or what not but Johnny Carson is the biggest certainly the biggest television star the most powerful television star when it came to um certain aspects of entertainment I you know and and and um I I'm I'm a gas that people have forgotten about him as quickly as they have in this show part of the show is the reason to celebrate um you know what we consider to be the greatest body of broadcast work in history that of David Letterman but if David Letterman is Michael Corleone obviously Johnny is veto and back in the day if you're a comic and you're on Carson there is something called the Carson bump you know you you you get on there and the next day I mean you were on The Tonight Show and and your your life is has forever changed obviously things have changed by this time that you hit Letterman um now you've got the Joe Rogan bump I mean I don't know if there's anybody else out there who can bump somebody the way Rogan does I've had I host a men's mental Wellness podcast and I've had two people on that show who who uh were guests on his show and they talk about how life-changing it literally was one of them had a had a Kickstarter going when he was on the show and the day after the show the kickstarter had three times the amount of what the goal was like it just crazy stuff and standups as well uh feel that now where you are the landscape has changed entirely but you show up and you do your spot on Letterman any noticeable difference at all was there a letterman bum no okay at that time and that was true even you know strangely several years earlier no Rodney dfield young comedian special bump you you mentioned that and and I knew that that was a question I was gonna ask so nothing changed in fact I can tell you Mike the only bump in recent years that I can definitively say H has happened in standup other than people going on Joe Rogan is Nikki Glazer's appearance on the Tom Brady roast absolutely changed her career overnight absolutely doesn't happen really anymore nope that's a complete exception to the rule yep yep uh great great Point great example um you know I was down uh I was down in La uh for the Netflix is a joke Comedy Festival and and and I arrived down there the day after the roast and I went to see Dave live and a couple other a bunch of other things too we've talked about on this show um and everybody was talking about it everybody was talking about it and I'm a Canadian that's down in LA to go see these other things and whatever and all these people were talking about that that was one of those moments um congratulations to Netflix for for for for getting that even though things are getting as diluted as they are you know they're throwing on these live specials and and and uh and they're seemingly not censoring um I'm going to be real real careful I believe I believe I'm see this is okay I'm going to get to this now before we get to your second appearance because because and I'll tell the audience here uh Hugh first appearance was just before 911 a couple months before and his second appearance was you know less than a year after um you know that atrocity that happened and so I want to ask you about that like I'm super super curious um but now we're talking about this I want to I want to kind of get to it here um you know I think about uh these moments in comedy where comedy is a guardian of free speech and and I I I'm a True Believer in that that that comedy really really is you know ridiculously you know these people are are are are literal guardians of of free speech I'm a big believer in that and and um you know when I was growing up it was sort of the right when it came to music and things like that that were trying to censor you know the hip-hop community and all of that and and and and and the left would stand up and say no free speech is the most important thing in the world and in our lifetime we've seen it kind of flip and go toxy Turvy a little bit where um you know comedians are getting you know censored canceled all of that kind of stuff um you have a very interesting take in this because you have seen that whole culture shift and evolve in your uh in your tenure and I'm super curious if you have anything to say about that if you're if you're are you a guy that says hey as long as it's funny it's funny um do you think that we're learning from mistakes when it talks about comedy being a a free speech kind of a piece do you have any opinions on that yes I'm a free speech absolutist so similar to you I feel that comedians have every right to say what they want to say on stage yeah I also believe that if a comedian's for profit doing this for a living they have to have a thick skin enough that if an audience object to what they're saying or is offended by them then that's part of the deal you go on stage and say something that pisses someone off if they want to post their protest online or organize a social media thing that's what that's their right Y and you have a right to respond so I feel like the only thing that really offends me Mike about standup is when it's unclever and hacky and easy I don't think there should be a law against that and if ComEd wants to do hack bad material they have every right to yeah but that's what really bothers me it's not a joke any joke about sexuality or race or religion or gender yeah it's not the subject it's how the joke is done and I'll take it even further and say to you that I don't agree with this new philosophy where people say Hey you know that was punching down and that's mean it's like screw that yeah yeah there's plenty of great jokes that punch down yep and I don't care about if you punch down with cleverly it's comedy yep you're allowed to punch down if you punch down in a way that comes off as just more mean than clever y well then you're gonna get a lot of hell for it I'll give you example please of a punching down joke that I wish I had written Mitch Hedberg has that joke where he goes he was watching TV and he saw a public service commercial for a girl named Lola who was um a paraplegic and deaf and blind and they said Lola doesn't understand the word can't they said uhuh and Mitch thought to himself not only is she blind deaf and crippled but apparently she also doesn't comprehend simple contractions yeah brilliant that's a perfect Mitch Hedberg joke that is but think about it yep he's making fun of someone who's Afflicted who's helpless is that punching down well it's not punching up yeah but I'm fine with that Joe that is a beautiful example and so I don't really to me this whole thing of comedians being cancelled is kind of a myth yeah because from what I understand Chappelle didn't lose money no he got in hot water and people he didn't lose any money and Tony Hing Cliff's career is on fire I was about to ask you about kill Tony Y just go down the list of comedians Shane Gillis is at the top game making millions like who's being cancelled unfairly Michael Richards got cancelled yep yeah one of the earliest examples of it yeah he's not that good a comedian so he's never tried to come back with new material yeah he was never that good a comedian yeah yeah more of a performer like back to go back to Fridays and things like that yeah absolutely other than him I don't really know any comedian who's been cancelled I know comedians who've faced protests yep and again that comes with the territory you know Louis CK has every right to perform and do whatever the hell he wants but if people want to pick it outside his venues or say well like okay well then deal with it yeah well my example to that is and I mean I feel the exact same way that you do and I think some comedians are now like looking at this going oh if this is the chess board okay I'm going to Castle I'm going to do this move here I'm going to I'm going to you know I I I watched again go back to um Matt re's special and I go back I don't know if you watched Matt re's last special on Netflix or not but uh but but you know my wife introduced me to Matt R and it's one of those things where if my wife is saying hey can we watch standup tonight I'm like yes let's please watch stand up tonight I don't even care who it is let's do it and not surprisingly my wife had gotten for lack of a better term turned on to Matt re and um and and and she's like I really like this Matt re guy and it's like yeah a lot of your contemporaries also really like this Matt R guy and and his crowd Works amazing and and so let's watch it okay and we watch it and the first three or four minutes he's doing material that is in my mind clearly material that is meant to get people potentially upset and and of course it happens and the and and and four or five days later you hear he's in the news for these things and he's got these amazing comebacks for those things and I'm like oh that's a brilliant guy right there that's a guy who is taking advantage of things but the example of what you're talking about that I go back to is Howard Stern you know you think about they they even said it in the movie you know the people who love Howard Stern their average radio listen is you know 90 something minutes the people who hate Howard Stern their average listen time is two hours in whatever time like it just it it feels like it's the same thing with the new generation just packaged in a new way I don't know if that's accurate to you or not I think that has some truth to it oh that's fun okay well thank you for thank you I I wasn't necessarily going to go down that path with it with you but I knew that your opinion would be uh more than educated because you're still such a writer uh prolific writer with with things all the way up to this day and and and and uh I'm curious how much the writing has changed well it doesn't come as easy as it once did because I think that the problem and I've read this about Ma mathematicians yeah mathematicians do their best work when they're much younger because they're not aware of all the criticism and rules their minds are just free to go where you want yeah the issue with me is because I've done it so long things will enter my mind that will like interfere with just that pure you know creative uncensored aspect that makes sense that makes a lot of sense um yet wisdom is here and and and you know the through through through all the years of of of the experience you know wisdom shows up and and and it's uh it's it's a very cool cross-section of of of a different time in one's life um let's go to your second your second visit uh your second visit is like less than a year after 911 and you had an Osama Bin Laden joke you had a you had a Taliban joke um again very good very clever it was it if there's such a thing at the time and place of a liked Taliban joke that's what it was um any push back whatsoever any discussion on your Set uh did how much was Eddie you know making sure that you were uh the tone obviously had changed at that point Yeah Eddie was um he always you know proved every single joke but I don't recall any issues yeah with that yeah so was do you remember did I do a joker that said about um a girl said to me something about um uh make it she she was a lesbian and she said who knows what okay so that joke what was the guy's name Frank who makes out better than Frank yeah so the way I would normally do that joke Mike was hey I I'm openminded and all I love women but nobody gives a like Frank oh and it was making it you changed it to out okay makes sense makes sense I said nobody French kisses right right um yeah that's what it was nobody French kisses like Frank that's what it was yeah so that's the only time I'd ever done that joke as French kisses but it always worked when I was practicing it with Eddie it worked great yeah so oh yeah it has a French kisses is better than makes out too I remember as makes out French kisses obviously is is is way better right um okay so so the second time that you're on um any uh any difference from the first was it uh well I was a little less nervous yeah and um I was more just yeah this time I knew what the theater looked like yeah Al I was I'd say I was looser but I will say that the effect of my baseball first base coach was uncredible so Eddie told me that Dave was going around the office imitating bit for I'm gonna ask you to do it please do it say can you give us a Bobby come on can you give us I'll give you a Bobby but the other tell you is I got a personal typed letter from um uh Mary Downey or who was the other female producer Mary Connelly Mary Connelly and who's is there another woman uh uh yeah there's a couple of Marys that were there um not forget Mary who was another woman who was sort of Barbara gains Barbara gains Barbara yeah Barbara wrote me a letter saying we're still all doing your baseball bit around the office cuz you did a call you did a call back to it you did it really really quick you did it really quick the second time you did it too I did the call back on my fourth appearance okay is that when it was okay okay okay yeah yeah yeah yeah yeah that's right um and yes you did a call back to it so oh that's fantastic know that I did a bit that had that big effect on Dave and the staff and there were there were there were it was funny because um I really I don't know have you ever cross pass with Jeff Alman years ago years okay I love Jeff he's a friend uh I'm so I'm so honored to say that Jeff's a friend and I I I'll make him say butt steak I'll make him say you know creepy baby was something that he would do he would call out the staff and and and um and and and just he had these little characters or whatever and then the people in the staff would sometimes imitate them you got one of those that's fantastic and what was it can you show it can you can you give us one do you do come Onie there it is um that's got to be gratifying that's that's that's that's super cool to have that as okay so now we're 02 to 05 05 is your next appearance I believe what are you doing what's your day job at this point are you still doing lots of writing are you still doing lots of standup um I'm now executive producing my own series with Spade yes with Spade okay so that's when you were doing Spade at the same time so you're Moonlighting now your standup is more like a Moonlighting gig correct okay and uh that must have been a lot of fun taking essentially the Hollywood minute and turning it into a show is is is really if you're to sum it up right that's right that must have been a lot of fun that was a real lot of fun and all the things I learned about producing from Lauren Michaels after spending seven years at SNL yeah I could now apply but I was the boss so I could bring in my own writers and cast and it was great okay now again again more tangental Letterman stuff here uh Ferguson I think Ferguson would have been shortly after that right oh Ferguson was right before that oh Ferguson was before that okay okay I'm sorry I'm I I Haven it mixed up so when you went to work for Late Late Show with Craig Ferguson kilborn had just left they brought you in did you work directly for Peter Lali yes okay I need a couple Peter Lali stories because this is a guy and I mean you know again once again hopes prayers love goes out from this show to Peter Lali UNT it just doesn't look like we'll ever be able to have a conversation with him but at the same time so much love to this man um you know we all just really appreciate Peter Lali uh so he hired you to come for lack of a better term was it was it clean house a little bit like to kind of get the CH change the culture put in the unenviable position of they said Hugh every writer here is on a 13-week contract y each time their contract comes up in the next weeks you have to decide whether to keep them or fire them wow that is UN unable HED any of them how do you how do you tackle that like are you doing team meetings to get to know these people and their sensibilities do you have ideas as to like how how do you how do you do that because the two Craigs were very very very different they were very different In fairness I was just evaluating their pitches and their joke writing yeah and their sketch writing based on what I was seeing in the writer room and how they would respond if I gave them notes yeah and Craig had his own opinions even though he was never in the writer room yeah so he's like I think we should get rid of this person and I could either go yeah I don't think they have your s or go you know Craig they actually wrote four of your jokes that you did last night and he wouldn't have any idea that right so I tried my best to be fair about it what a crazy job um I mean I I I I don't imagine like when you look back and you say hey I worked for The Late Late Show with Craig Ferguson which was an amazing show I don't imagine that that would have been like how long did you last there a year you were a year six months I was there a half a year okay Craig was a little upset because the C my series the show show with David Spade was green lit and so my contract they were pushing me to sign and I said I my series just got picked up yeah so I left Ferguson to go do my own series and he must have understood that like I mean that's that's a ultimately he did yeah um yeah you wrote for Drew Cary did you two know each other back then sure okay Drew and I knew each other long before that though okay so you and Drew did but you and Craig like you and Craig met met on that show sorry so oh here's a crazy one for you okay the season I did of the Drew Carrey show it's final season yeah Craig only appeared in one episode because they had changed the plot line Drew no longer worked at the same job and Craig Fergus was his boss of the other yes however however Craig had signed a player play deal where he was paid $3 million no matter how many episodes they used them for they used him for one episode he got paid $3 million to have free time to do whatever the hell he wanted good for that guy show up once good for that guy uh pay or play I mean obviously you know if you're if you're a fan of of the late night stuff Bill car or whatnot that's exactly what Jay Leno had when he had the Jay Leno show and part of the reason that the shuffle at NBC in 2010 happened was because of a contract very similar to that with with with with Leno he actually had a play and pay contract which is uh which was really unheard of at that point that's very interesting so so when you came over to to to work for Late Late Show there wasn't really a connection with you and Craig at that point zero no even though he he didn't know that I had written on Drew right but again that's because he hadn't appeared on Drew that whole season oh that's so crazy and so how do you get that job like like Peter Lali guy who did the interview came through um the wonderful executive Valerie Sher okay with NBC executive and she was a fan of mine CBS oh yeah oh sorry CBS she had been at different places but she recom and then Rob Barnett yeah knew me from letterin yeah was like well I know H standup quite well and so when my name came up they're like is he interested would he want to be headwriter so that's how it happened oh that's crazy um and do you have any Peter lalii stories I mean you know we we all think of it please Peter was from Europe Y and um Holland right Holland right yeah yeah yeah yeah so the one story I have for you is he was very audite and talked like a European sophisticate not a so it's Craig Ferguson's birthday and so they gather all of us into the kitchen to celebrate his birthday and there's a lemon cake there why I don't know and Peter lelli turns to me and says so Hugh do you fancy lemon cake who says the word fancy it's the 19th century the other story I can tell you and I will give this a asteris and say I've been told that this story is true yeah okay okay y y is that he was from Holland yeah he apparently was telling some people that he knew Anne Frank they GRE up their families like knew each other because agewise that actually tracks he would have known an Frank it's possible and so someone said to him that's incredible Peter that you because you know he was a a European Jew as well absolutely and the story I've heard Mike I swear is that he goes she wasn't a very nice girl I want that story to be true so bad me too me too but we'll never be able to find out from the late Peter L Alle you really said that oh oh man that is it's the greatest that is a fantastic story um it's the equivalent of saying yeah Nelson Mandela's kind of an yeah I was a cellmate in prison he was a jerk yeah yeah that's oh that's great that's precious too um I appreciate you you going down that path uh for me here um and then' 05 you appeared and then uh 2011 you appeared one more time before uh before they uh they they pulled up the tent uh tent pegs in 15 so you did get a chance to go back how did that how did that happen was that still there sorry I don't think was Eddie still there at that point yeah I think he was there till he was yeah yeah he was there that was fun because I was so loose yeah now it's my fourth appearance first time bringing the violin out you brought the violin out that's I did that for the third show actually oh that was the third show okay yeah I watch you know Paul schaer had hired me and Bill Chef to write for the Chevy Chase roast there we go so Schaefer had become a fan of my standup oh that's great and I wrote the joke the infamous joke Greg Geraldo our next comedian has had more failed Pilots than the al-Qaeda that's a perfect roast joke right that is a perfect roast joke even today I wrote All of Lorraine Newman roasted Chevy and my premise for her was that she when she uh was cleaning out her desk at SNL she found Chevy's diary from 1976 and so she's going to read excerpts from his Diary Of course these are all made up mik I did was um May 11th 1976 I gathered Lauren Belushi and everyone and told them the sad news that I've decided to quit SNL to pursue my dreams to one day host the shittiest talk show in history on Fox wrting Hollywood minute right sure oh God yet oh that's what Hollywood minute is it's it's yeah but uh no so Paul schaer and I got along great and so when I came back from my final Letterman appearance that's when I decided that somewhere in my set I was gonna call back come on bobie there we go okay the audience had no clue what I was talking about unless they were fans of my standup and knew the bit but I'm going to assume most of the audience didn't know that bit Yeah but I didn't care I didn't care so after I got a big laugh on a joke I just turned and looked at Dave real quick yep remember he cracked up he loved it that is the great I I've had so many conversations with people both on camera but then Al also off camera and I'll tell you this Hugh there are so many humans walking this planet right now where one of their crowning achievements highlights of their life is that they made that man laugh and and they just love doing that that must have been such a cool feeling at that point it was really cool it was also cool that I was so loose that I could do that yes I mean it was unscripted I hadn't told Eddie I was gonna do it yeah um and I just decided I can get away with this oh that's fantastic um I I got to tell you this of the four appearances um you know sometimes I'll talk to somebody on this show here like I watched I probably did watch every single late show it was the way Dave describes Johnny Carson is is is Johnny would put you to bed every night and and it was the constant right well for me my constant was was David Letterman and and everything that uh everyone did your s included that to contribute to it now I probably watched every Late Show I had them PVR or DVR um you know and and and would catch up on them in case I was on vacation or something like that I would always watch them and there are memories core memories that have stuck in my head and your standup I'm pleased to say is one of them because when when I was going through your appearances again I got to and I got goosebumps the moment it started because I was like I love this bit and it was the bit of the hip-hop right the hip-hop uh acceptance speech at the awards show and we're going to move to Awards shows here because I know how to segue but before we do I need to tell you the hip-hop artist thanking all of the Jewish Executives is one of the funniest things and you did it you did it twice you did it once and it was really funny and then he went and said something else and then he came back and did it again and it was I can remember watching it when it happened and going oh my God that's one of the that's one of the funniest jokes I've ever heard from a stand up thank you so I have to tell you that uh don Giller is gonna come back and tell me this is an episode of the Chris Farley Show because I'm just saying oh you remember when you did that that was awesome I don't care I don't care it was so good and by the way I think that that joke would still play today I you know now that you're saying it I think it would too yeah it's just you're right it's so perfect and um so so I want to I want to segue that a little bit to you know you you you've got the idea of an awards uh ceremony in your standup here and whatnot you've written for a lot of award shows I have you know my current gig is I executive produce and write for the writers gold Awards here in Hollywood I've done it for nine years that's a big gig it's a big gig and I've turned it into a comedy show meaning the hosts have been uh Janelle uh Janelle James didn't bur do it no chelse Patton Oswald Lisa kudra yeah presenters are Bill Burr yeah Bill bur okay yes yes so it's a real comedy heavy show so I love so it should be it's the writer Guild show it should be like in my mind when I got hired I told them if this isn't the best hip hiple written writers the writing of the show if it's not the best something's terribly wrong you're the writer's Guild that's exactly right so oh yeah not televised but it's a great show and we shoot it with five cameras like a television show so why why why aren't some of these moments out there like I mean you know sadly it just the media never gives it other than the results of who won the awards they never pay much attention to the content of the show but I wish they did because it's a really entertaining funny award show but pardon my language but who gives a about that when there's YouTube and you could put it out there and get a million views and monetize the thing like you could that I agree with you they will maybe one day they will but um yeah I've done that I I did do the awards for several years yeah the one that nor McDonald hosted the greatest award show in the history that changed the SPs forever it scared the out of them they've never done a show with the comedy of that show because a lot of athletes we pissed off a lot of people sure a lot of people you know the joke Bill Chef wrote the joke about uh it was a segment where I had will frell as Harry KY of course oh will frell's where Harry KY is amazing and remember he goes John Elway you did you just won the Super Bowl how about going nuts and getting those teeth fixed and they cut to John Elway fuming camera and the next morning oh man the president of ESPN was calling me up and saying how dare you but here's what's fascinating every single joke was on the teleprompter approved by the network fantastic they approved the jokes we didn't we pull a fast one on them no they just didn't realize the brush back they'd get yeah and standard and practices I mean they're looking for stuff that's going to offend or like like in a in a in a in a you know in a in in an UNC way not not not clever stuff like that like it's they didn't expect that they forgot that famous athletes often have no sense as a humor right so they just couldn't take it I mean I had a joke I said Ken griffy Jr you're not half as good as your father keep trying though which of course is absurd because he's a lot better than of course he is of course he is Ken griffy was angry at the joke oh good Heavens oh that's such a perfect joke thank you that's like oh my goodness oh we had the joke Tiger Woods you're you're one of the eight or nine best black golfers in the game today wait a second hold on a second that Rings such a does it did Norm do that as Larry King no what you're thinking of is I wrote the joke he said that um Michael Jordan is one of the eight or nine okay greatest African-American best I basically stole from myself you have a good memory that's fun I remember I love Norm doing Larry King I love Norm that's what I did oh God I also had Norm say that John Lara one of the greatest people of the 20th century has got to be John Lara greatest person of the 20th century that's such a perfect Norm line it is it's a perfect Norm line um so how well do you know shef do you still know shef at all yeah so Chef wrote I'm trying to get him on the show by the way I'm desperately trying to get him on the show my buddy who wrote last days a letterman Scott Ryan he wrote the forward and I'll tell you where my hope comes in he told Scott no three times to running the forward and Scott asked a fourth time and Chef's like yeah let's do it right now and he got on the phone with him and he and he and he went and did it and so I'm I'm I'm literally relying on the fact that Chef is known to sometimes change his mind I adore this man I would really love to have him on this show he actually wrote on the writers go Awards a couple years ago for me so that was cool fantastic um let's talk a little bit about contemporaries comedy writers I mean like like when I told you I could do this all night with you now I'm I'm kind of proving it I could you thank you very much for for for doing this I gotta have you back one day because I mean obviously I don't want to take your whole night uh but but let's talk a little bit about your um uh contemporaries folks in the in the in the writing business what are you doing right now I want to plug stuff as well but let's talk about some of the contemporaries like shaft some of these people that you enjoy collaborating with now sure so um Joe O'Brien who was a a longtime writer at the Craig Ferguson show after I left yeah um and then he was one of my main writers at the Showbiz show with David Spade yeah he's the headwriter currently of the writers goat Awards okay there we go so he's great um Stephen Krueger is a writer friend of mine we just wrote a a pilot together sort of a dramedy Series yeah so that's pretty cool you're pitching it you're at that point where you're pitching it now pitching it now exactly good for you yeah pitching it now um well else can I tell you about uh I mean those are the two that come to mind cool very cool they're your collaborators right now um I just want to go for my cheat sheet really really really quick one more time you've worked with Fallon as well look I mean again the number of late night personalities that you have worked with we've talked about Conan we've talked about Ferguson we of course you know your stuff with Letterman and then and Paul and and and and and Chef and all that stuff you've worked with Fallon as well yeah I just worked with Jimmy um he I had him as a presenter on the writers go Awards this there we go yeah H have you any interaction with Kimmel no only that we ran into each other at the Super Bowl in New Orleans several years ago okay together never worked together um I also know that you worked with Gilbert godfried and I've got a big big soft spot for him in fact he on last Comic Standing where I was a producer writer I probably wrote him 25 jokes where he made fun of the other of the comedians on last of the contestants he roasted the contestants you you wrote you the contestant every single joke and it was so fun and to Gilbert's credit there were some jokes where I'm like yeah this one's kind of he's like no I want to do all of these he did every joke wow oh that guy I I'm good friends with a guy by the name of Steve Wier I don't know if you know Steve or not but I know of Steve Wier okay so he is a very very good friend of mine we've become very good friends through the show here and I you know I love listening to him talking Dave's voice because he was only there for a year right but he's the guy that brought in Calbert deor he's the guy that wrote the uh oh so I gotta interrupt you yeah tell Steve hello that when I met with Letterman when I was 19 years old yeah I met Steve at the show he was was there and he was kind to me and he asked he said he would listen to my wnyu radio show tape and he listened to it and he called me and said you're very funny you've got You've Got Talent keep it up that is Steve Weiner to a to a always remembered that I wouldn't have had cavat on this show I wouldn't Mr D Cav came on this show I wouldn't have had it if it wasn't for Steve and Lori his wife he's one of the most giving people you'll ever beat and uh you can tell him that I've always appreciated that oh oh oh I cannot he he watches all of them so he's going to hear this and it's going to be great for him to hear that I love that I'll listen to Steve and he can talk in Dave's voice even though he was only there a year but where Steve really shines is after Dave he went to work uh and wrote for Robert Klein for a long time and he can still like right now get into Klein's voice say something that Klein would say and do that you have written for the the the the plethora of people you have written for is unbelievable how do you get their voice the way it's just something that I've been able to do since I was a little kid I Channel people I just Channel them and once I've channeled their voice it's very natural for me to write in their voice that's fantastic that you can do that um I'm so grateful that you've taken this time here tonight what are you working on now what are some projects that you're plugging other than the podcast that you and I are going to talk about off air what are some of the things that you're uh you're you're working on now one thing I'm pleased to share with your viewers is that since people are interested in getting into writing professionally comedy writing joke writing I have a whole new career that started during Co of teaching at the highest level I teach at Harvard University and I teach at Chapman University yeah Advanced sketch writing but I also do private coaching for people who are interested in writing for late night improving their joke writing and so they can find me at q.com and I have clients from all over the country who are writers at different levels can I call you a Harvard Professor are you a Harvard Professor I'm an adjunct faculty member holy smokes do you hang out with the is the Lampoon still doing its thing do you hang out with those do thing and I my I'll have my fourth Harvard class starting this fall congratulations do you enjoy it um I love it I really do wow I interrupted you there when I asked that question yeah so so hf.com anyone out there who's interested in you know my services to help you with your comedy writing let's do it you talk about the culmination of a career doing what you do at Harvard um there's a lot of swagger to that that's pretty great they're Swagger I agree and know I I always tell people they may not be the funniest students they're the hardest working I'll say that yeah they turn their homework in on time this is why they're at Harvard but then Chapman University you know is now one of the top five film and TV programs in the United States yeah so I teach there I'll be doing my fifth class for them starting this fall too do you um I I steveo Donnell has become a friend and and and he's doing it at NYU and he talks about he talks about the bond that he builds with these with these some of these kids and and whatnot it must be so gratifying to talk to this generation and and and impart again we go back to wisdom to bringing some of that wisdom to the to them that that must be incredibly fun do do you do you develop connections with these kids that I do because you know some of them are going to move on to have professional careers many won't but regardless I do develop a really cool rapport with them I'm so happy to hear this for you Hugh and uh and doing still doing the Writers Guild uh as Awards as well you're still doing that that's right the this year will be the show will be I believe February 15th awesome yeah awesome and are you okay so just just for us us lay people who who who are wondering February 15th okay so you're about a half year away are you um how much of the show is already taking shape like are you working on that at all in any capacity or is it the new year yeah I'm thinking about who would be a good host yeah thinking about that and I'm always looking at TR friends and things happening in Hollywood that we can make fun of of course it's a half a year away so something that could be in the news right now may not be as funny then right yeah but sometimes there's something that has staying power so I'm always keeping a track of of what's funny uh speaking of which you segue right to my last question it's like you've done this before but you don't know what the question is I uh I'm curious I'm curious about your take about John meany's Show on Netflix what did you think of it I liked it I think he's a risk taker and I appreciate the fact that melany never he's doesn't let Nostalgia rule his career he's always trying something new that's apprciate that it felt a little bit like late night um to me is is just just a little bit like that and I was very curious about your take on it h you have been um an incredibly incredibly generous with your time uh tonight um and and I mean the moment I mentioned the I'm the host of the Letterman podcast you were like enthus I atically yes there was no convincing you on this and I and and and you certainly showed that right from the very beginning here um you know another another famous son from Indiana Hugh thank you so much for taking time out of your day to be on the Letterman podcast today I cannot thank you enough and I can't wait for our path to cross in other ways moving forward it was my pleasure and I really love that you're doing this podcast and um look forward to seeing what other guests you get and we'll reconnect sometime I can't wait um I'll do a really quick outro and then we'll say our goodbye privately that's okay with you yes all right awesome uh and we'll do it like this okay so that's why we do the show right there um this has been a perfect example of of of of the Time Capsule that we are creating creating this body of work that celebrates another body of work that's kind of how podcast Works many times um this has been another episode of the Letterman podcast with Mike Chisum coincidentally I am Mike Chisum thank you and good night BB come on Bubble overcoat and Underpants