Another remarkable era in late-night television is coming to an end as Conan O’Brien signs off from his TBS show. For a substantial segment of comedy fans, it feels like a huge loss, even though he’s heading to HBO Max with a new show sometime down the line.
To help give O’Brien a proper send-off, Vulture reached out to 12 comedians and actors, most of whom credit his tenures on NBC and TBS as being not only highly influential on their careers but also their lives. Several themes emerged during these conversations: O’Brien is one of the funniest, if not the funniest, people on the planet. His mix of Harvard smarts and crass bits made them feel that they were seen and less alone in the world for being a bit weird. As a host, he’s one of the most generous that guests have ever encountered, elevating them to a higher level of comedy, often at his own expense. Some are still in awe of the things he and his extremely talented writing team were able to get on network TV in his early years, not to mention his evolution as a host and an interviewer. Some, to be sure, are still quite pissed off at NBC’s handling of his brief time as the host of The Tonight Show. All of them sing his praises as being one of the sharpest, kindest people away from the camera.
Despite the fact that many of them describe him as awkward, geeky, stupid, and other pejorative phrases, all of it is said with the utmost respect and love. Here, how these dozen people — who include comedians who have appeared on his show from its earliest days, fellow talk-show hosts, and a former intern — recall their favorite Conan moments, bits, appearances, interactions, and so on. (Spoiler alert: There’s a lot of talk about the greatness of the Masturbating Bear.)
I started watching Conan when I was a teenager in high school. All of my friends connected to him on a way deeper level than with Leno or Letterman. That isn’t a dig at those guys — Conan just lit up our brains. And then, upon further research, we found out that he wrote for The Simpsons and Saturday Night Live during our favorite years of that, so we were instant fans. We thought he was so creative.
He’s likable, and that’s the most important thing. You can tell he’s very, very smart, but he’s not pretentious. He’s very self-deprecating. He knows when a joke tanks. He’s an improv master, so if a story or joke or guest has tanked, he’s right there to pick up the pieces and make it funny. He’s also very creative and has a distinct, unpredictable comedic point of view. Comedy relies on the element of surprise, and he’s so quick-witted and interesting that you’re just along for the ride. And he’s a bit of an underdog, too.
His comedy really shaped my comedic sensibilities and my worldview. Me and my friends, we were so invested in it because we felt ownership of it. His comedy wasn’t like anything else. We felt he was speaking directly to us. Johnny Carson was before my generation, but from the tales I hear, it was a monarchy: “You have to impress King Johnny.” I don’t like that. Who are you to be the one and only judge of comedy, which is completely subjective? Conan was the antidote of that model, where he felt like your friend. He wasn’t arrogant; he was silly and absurd, a master of non sequiturs. There was a subversiveness and anarchy to it that became part of my comedy growing up and definitely helped shape The Eric Andre Show.
I’m still, to this day, the most nervous when I do Conan because I grew up watching him. He’s my idol. My first appearance, I was pretty nervous. But it was one of my favorite ones because I got to be as insane as I wanted to be. I’ve tried to be more grounded on there as time goes on so I’ll connect with the audience more without being boring. I want the audience to like me, I want Conan to like me, and I want to have my segment be the funniest thing on the show for the episode, so it’s nerve-racking.
Tommy Blacha wrote for Conan, wrote for Ali G, created Metalocalypse, then The Eric Andre Show. He was our Obi-Wan Kenobi in the first writers’ room because we really didn’t know what we were doing. We were really straining, where every segment had to be this brilliant, groundbreaking piece of art. He stopped this right away and said, “Whoa, whoa, whoa. If you overthink, you overstink.” I told Conan that on his podcast, and he’s like, “I actually came up with that. It’s ‘If you overthink, you begin to stink.’” When you run a room full of very smart people coming up with very stupid, childish stuff, then you are tapping into your id. Once you get really smart people tapping into their id and the childlike, impulsive parts of their brain, that’s what makes it comedic. It’s that juxtaposition: this highly intellectual writer writing poop jokes that a third-grader can write is what gives these shows their magic and universal appeal. They’re operating on many levels, but comedy is primal. Art is primal. It’s only the art professor that says art is intellectual. Art has to pander to the caveman and cavewoman within us. It’s playing to your heart, not your cerebral cortex. It’s a smart mind that drove you toward a stupid premise.
He’s honestly one of the smartest people in entertainment. He’s never punching down, never mean-spirited. He’s very, very tall and handsome and intelligent — he could easily be the jock or the frat boy, if he chose, but he doesn’t have that in him. And I think he’s going to do more of the same, just in a different configuration. He’ll always be himself. It’ll be an evolution of everything he’s built over the past three decades, so I’m excited to see it.
I really came to comedy late. I didn’t watch SNL or Late Night until college, but my roommate would stay up and watch Conan, so I was like, Oh, I guess I’ll watch him. And then I was like, Oooh, he’s funny.
The thing that really sets Conan apart from other people is he’s weird. He’s a redheaded, tall, gangly, weird man who doesn’t shy away from being weird. My comedy is a little off the beaten path sometimes for some people, and it was nice to be able to turn on television and be like, Yes, people do want things that are a little weird.
I remember being incredibly nervous my first time on [his show] because I was trying to promote my show that was on MTV. He was so kind to me. He came to the dressing room and talked to me like I was a normal person. It instantly made me feel okay. Then, after the interview, he leaned over and said, “Any time you want to come back, you’re great.” I mean, somebody who’s been in the game for so fucking long, who has achieved so much, who’s beloved, who’s really funny, for that person to lean over and go “You’re really funny” is a validation that you don’t get often in this business. He’s also really great at give-and-take. I’ve had some interviews where maybe the host wants to be the funniest or whatever, but Conan is really great at letting you have a moment to shine. He really elevated me in a way. I’m indebted to him.
My favorite time being on the show, during the pre-interview, they said, “What are you looking for in a man?,” and I was like, “A big dick.” The producer said, “Are you really gonna say that?,” and I was like, “Am I allowed to say that?” And he’s like, “I think Conan’s response will be funny, so I do think you can say that.” Then I said it, and the audience went wild. And then Conan’s reaction highlighted his mentality: That was the funny bit, and I’m gonna give you this reaction that makes it even funnier.
Some hosts are very much on autopilot, but he’s not; he’s super-engaging. He’s not looking through you. He’s looking at you like, What are you gonna give me next? Because we’re playing fucking tennis. You’re gonna bounce the ball at me, and I’m gonna lob it back at you. Which is always fun, because sometimes you go on shows where you’re like, Huh? I don’t think you even like me. He lets you do anything you fucking want.
Late night is going to be a little more boring without him. A fun little weirdo is leaving! I hope he doesn’t read this and be like, “So, Nicole’s only gonna fucking call me a weirdo the whole time?” I mean it fully, with love, but yeah, he’s fucking weird! I like being weird.
I didn’t know a lot of people that were talking about Conan O’Brien for his first couple years, but that was kind of the magical thing: If you found someone in your life that loved Conan and loved the show as much as you did, it was almost like you were in the club. You spoke the same language. The first few years were magic to me. I remember feeling, I cannot believe that this is on television.
It’s like he was playing a late-night host. This thing that we’ve known our whole lives as an adult thing — they wear a suit, they’re buttoned up, they wear a tie — it’s for your dad after work, but this one was for us. He straddled the line between buttoned-up late-night hosts and young punk dum-dums. He was so goofy and silly and whimsical and absurd. It was so stupid, truly, that it really felt like he was getting away with something.
I remember being on vacation with my family, 12 of us in two hotel rooms, cots everywhere, sleeping on the couch. Everybody in my room was asleep, and I was quietly watching Conan. It was the first time I saw “In the Year 2000,” and it killed me. I had to stifle laughter so I wouldn’t wake up my aunt. LaBamba from his band singing in that high-pitched voice was the funniest thing. It was so stupid. It’s taking a risk; you can tell that they think it’s funny and they trust their comedic instincts so much. Any other late-night talk show would have done, Here’s a funny bit about the future, and here’s a list, or whatever, but they did the singing and the lights and it was just so fucking stupid. And I absolutely loved it. That really hooked me in early. It defined what the show was, that they were going to march to the beat of their own drum. That gave me and so many other comedians the freedom and the confidence to trust our own voices, too.
Every memory I have about my first time on the show is good, and that’s not always the case with every talk show. I remember getting advice from an older actor friend who had been on the show and him warning me like, “Don’t let your guard down. If you mess something up or say the wrong thing, he will absolutely destroy you,” which, of course, is one of the things I love. I remember having the thought, Yeah, Conan does love to destroy a guest. He loves to destroy the audience. He loves to destroy Andy, but the person he loves to destroy more than anyone else is himself. No one kills Conan more than Conan kills himself. It’s part of the joy. It’s part of his gift as a comedian. It’s so impressive.
Now, Conan is a great friend. I don’t mean that like, “We’re so close.” I mean that he’s a generous friend. He will reach out, be the one to extend the hand. I can’t tell you how much that means to me. It’s still me in college with a VCR, taping episode after episode to show my theater friends, crossing my fingers that a Triumph or Amy Poehler as Andy’s Little Sister would come on. Those things don’t go away.
I was a little late to Conan, but it must have been ’98. My dad had seen the five-year anniversary special and he thought it was funny, so he popped in a VHS like, Oh, I gotta show my kids when they’re awake tomorrow. It opened this world up to me that I didn’t even know existed. I felt really seen by it, and I felt really special that I understood it, even though it was sometimes completely insane. From there, I got my friends into it, and we became obsessed.
I don’t want to say it’s the moment I realized I wanted to do comedy, but I knew it was a leap. The Masturbating Bear. The Walker, Texas Ranger lever. The string dance. Preparation H Raymond. So many Brian Stack and Brian McCann characters, like Minty, the Candy Cane That Fell on the Ground. Their announcer, Joel, and the things he used to do with him. “Celebrity Secrets.” The steely silence between Conan and Max. And the satellite channels they used to tap into, like Alienated Pigeon Channel, where it’s a flock of pigeons eating seeds and then one pigeon in a limo, sad that he’s not included. The Clive Clemmons Inappropriate Response Channel, where there would be a scene where a woman would be in the break room of her office, and she’d go up to a guy drinking coffee and say, “This coffee is really good, right?” And he would go, “Thank God for Saddam Hussein,” and there would be a stamp over it that said “Inappropriate!” Then there was the Babies Reminiscing Channel, which is a gag I’d do with my niece and nephew when they were babies. I would put them in positions where they would look like they were reminiscing, because it’s so funny to see a baby being nostalgic.
My dad bought me the In the Year 2000 book for Christmas. That was my first time being able to look at jokes in written form and study them and see which ones were funny. I can see that I was taking a course in joke writing. I was highlighting and writing notes in it: “Oh, this joke’s better than this joke because of this.” Early on, I was really interested in the detailed work behind jokes, and it was all due to Conan.
I admit I never wanted to go on Conan because it was just too much. You don’t want to meet your heroes and be invited into the world that you have on such a pedestal. I didn’t think that I deserved to be on it. I met him for the first time after my set — he walks over and says, “Great job.” He shook my hand, and I kind of held it and said, “You don’t understand. The reason I do this is because of you.” I think I blacked out.
I’m a lot like Conan in the sense of I’m not good enough to be doing this. That’s why I relate to him so much. Conan does not understand how good he is, and sometimes it’s helpful for me to remember that. I’m not scared to gush about how much I love Conan. I’ll never stop telling Conan what he means to me and having that sincere moment that makes him deeply uncomfortable. I always feel like, “Sorry, you’re gonna have to let this in. It’s true. You’re the best. You’re the GOAT.”
I started watching Conan in 1993, when I was 15 years old. Conan and The Simpsons were really the first thing in comedy that I felt was mine. It was the first thing that my parents didn’t get. Before that, I would watch Letterman or Monty Python and the Marx Brothers with them, but then Conan was the first thing that they went, “What is this?” They were really confused by it, so I think that’s why it’s so special to me. I’d go, “No, this is my thing.” He spoke to that.
Conan took what you found funny, which was crazy, conceptual comedy, and there was kind of a geekiness to it that I appreciated. You could tell it was him and his writers trying to make themselves laugh. There was nothing pandering about it. He set up his guests incredibly well, and people always seemed really loose and funny on his show. Like Harrison Ford — the first time I saw Harrison Ford be funny was on Conan. I didn’t realize he had a sense of humor about himself. Or when Tom Selleck had to say good-bye to his mustache because the mustache was dying. It’s “a comedy geek got his own show.” That’s how it felt.
Letterman would say things in a way where he didn’t care if the guest hated him. That was the danger with him. Whereas Conan could be sarcastic, but he always was trying to help guests out. You could feel that they responded to that. Every time you do one of those shows, you think you’re gonna bomb. With Conan, even if I had a terrible interview or the material I was going out there with wasn’t very good, there was not a chance I could bomb, because he was right there with you.
After doing that every day, I don’t know how you still get excited about being funny, and Conan still is the funniest. I had dinner with him and Marty Short a couple of weeks ago, and I was crying-laughing at that dinner because he’s so fast and so giving, like he is on his show. There’s no ego there. There’s no, like, It’s my show, so I’ve got to be the funniest person here. This is corny, but at that dinner, I secretly took a picture of the two of them to be like, I can’t fucking believe I’m having dinner with these two guys.
The thing that I’ve learned the most is how he’s a very deep guy. If you listen to his interviews, like his Stern interview, he’s very open. What he talks about in terms of anxiety and fear of failure, I definitely relate. When you talk to him, yes, we’re “on” all the time and messing around, but at the same time, there’s always a depth there that I really appreciate. It made it okay to be like, Conan deals with this stuff that I’m dealing with kind of secretly. You think, What’s wrong with me?, and Conan made me feel like, There’s nothing wrong with you, man. How could we not be a little crazy, doing this for a living?
When I was at SNL, after a while the idea of trying to make something like a sketch work or a character work, I just got exhausted. The last thing I wanted to watch or think about was comedy for eight years — and then years after that, to be honest. Then I learned from Conan, Oh, that’s okay. Own that. Actually, that could be a source of a lot of funny stuff. What’s going on in you can be a source of a lot of funny things, your own anxiety and depression. A lot of that goes into Barry. So no matter how you’re feeling about comedy, all this stuff roiling about you is a source of that. There’s always something funny about that, because it’s you. Even though you watch his stuff and it’s all kind of conceptual, there’s always, underneath it, the personal stuff.
It’s a thing you manage. People assume, Oh, everything’s going great. And you say, “Maybe on the surface, but underneath, there’s a lot going on.” As you get older, it gets a little bit more intense. Watching Conan over the years kind of accept this aspect of himself and be open about it, I respect that. To have a chance to talk to someone honestly about it is wonderful and makes you feel a little less alone.
I’m a comedian, but I’ve always sort of been a 50-year-old retired antique-store owner living in New Hampshire — I’m not really cut out perfectly for the lifestyle. That’ll make sense when I tell you that when I moved to Chicago, Conan was on one hour earlier, and that hour made all the difference for my lame ass. That’s when I really started watching him every night.
I’m sure everybody says Masturbating Bear, but I do remember Masturbating Bear. I was right at that age. I grew up religious. I wanted to do comedy. I was deeply ashamed of my sexuality, and sexuality as a whole. Not just my sexuality — I was ashamed of your sexuality and everyone’s sexuality. So I don’t think I’m too out of bounds to say having a bit like that is simultaneously juvenile but also strangely cathartic, to laugh at our animal nature. There’s so much lingering, puritanical shame, and they’re like, Literally, we’re going to shine hot spotlights on a guy in a bear costume, masturbating in the only way the network would approve, which is not a masturbation gesture but more of mixing a salad.
The silliness, it wasn’t malicious. It’s really interesting to watch some of the Letterman clips that have been passed around lately and see how poorly they’ve aged. I loved Letterman, but that’s what we thought late-night hosts were: They were sort of irritated, and it was so fun to have somebody else that thought the whole thing was a big joke, a playground.
That’s actually something Conan said to me when I did my talk show with him: “The writers build a playground, and it’s your job to play on it.” I took that advice to heart, but really I see him taking that advice. He’s a guy who understands that his job is to not take it too seriously. His job is to have fun and be silly, and he really excels with that.
I won’t bore you with the details, but Conan and I had a meeting, and he was so nice, really put me at ease. Then the next meeting we had, he said, “Okay, we’re going to go to TBS and tell them we found the guy for the talk show that will be on after mine.” I literally remember thinking, I wonder who the guy is. I didn’t think they were talking about me. I slowly put it together.
He gave me the keys to the playhouse, with no ego. He never held it over my head. He’d drop by the writers’ room and hang out with us. He’d make fun of me in front of everybody — I know that sounds like not a good thing, but it was a great thing, this way of being peers. I genuinely got dunked in the tank of becoming more than just a comedian who was on his show.
It’s not just that there are more people who are like Conan than we thought — it’s that there are more people who would like someone like Conan than we thought. He really grabbed those groups: the intellectual, awkward, funny person and the more straitlaced people that didn’t know that they wanted to have a goofy friend.
I’ve always felt like a sort of gangly, pale, smart, funny guy. And to see one hosting late-night, it felt like the guys that I ate lunch with in the cafeteria in high school. He gave us hope: Oh, we don’t have to become stuffed shirts, tough guys, or serious men. You could be respected, and you could be famous for being not only a pale, gangly man but for talking almost exclusively about being a pale, gangly man. He turned all of that into the car that he drove to the moon.
I think I started watching him his premiere night. I was doing morning radio at that time, so I got up at 3 in the morning. I wasn’t watching the show regularly, but I made a point to watch that opening night because I was such a Letterman fan. I was curious who would step into that spot, and I remember thinking, This guy seems funny and also clearly has a very dark sense of humor. His first show, he had this noose. I was reminded of that as I was getting ready to step into my own guillotine when my show started.
He’s obviously a very smart, bright guy and also just a naturally funny guy, but what is best about Conan is that he seemed to be doing things that made him laugh. I think that’s the best thing that you can do. A lot of people worry — I think too much — about what the audience thinks, and that never seemed to be a concern of his. I mean that in the best possible way, not as an insult. He really stayed true to the humor that he appreciated, from the very beginning to the very end.
When did I meet Conan? I think I maybe met him at Martin Short’s house. There are some people that are very funny on television, and there are some people who are not that funny in real life. Then there are some people that are funny on television and even funnier in real life. Conan is definitely in that category. He had me laughing hard for four hours straight. At a certain point, I wasn’t even talking to him; I was just watching him. He had a few drinks and adopted a German accent, and it was off to the races. He viciously insults people without any viciousness at all. You always know he’s kidding, but he never stops. I think part of it is being so big — you’re looking down on everyone, literally. Some people don’t even bother to try to be funny in what you’d call “real life,” but he clearly loves it.
It’s funny — Conan once said to me, “You know, I’ve not really seen your show. I try not to watch other shows because I don’t want to be influenced by them.” And I nodded and agreed, even though the truth was, Well, I’ve watched your show like 500 times. I’ve asked him on, I don’t know, three different occasions when he was retiring, and on the third time, he’s like, “Why do you keep asking me when I’m retiring?” I said, “Because I can’t until you do!”
I also feel I should mention Andy Richter, who I think is absolutely great and one of the most underrated people ever on TV. The chemistry they have is rare, and he really brings a huge amount to the show and could certainly host one of these shows on his own. Andy genuinely is a kindhearted soul — and manages to be funny despite that.
One of the bits that I liked — and you’ll understand why I like this in particular — was where he would do the bit called “Actual Items,” where it was basically him goofing on Jay Leno doing “Headlines,” which was itself ripped off from Letterman doing “Small Town News.” Conan would make up fake headlines from various newspapers around the country and then act as if they were real. I liked that because not only was it funny in and of itself, but it was also a little slap in the face to what was going on on The Tonight Show.
It’s a long story, but I was involved behind the scenes of that a long, long time before I was involved on television, when I dressed up as Jay and impersonated him for an hour. And then Jay made the mistake of inviting me onto his show, the “10@10,” the next night, and I continued with the assault. Let’s just say that that impersonation did not come out of nowhere.
But Conan, there’s no rivalry between us. It’s just friendly. I was mad for him. Sometimes I feel like I was madder for him than he was! I won’t go into it, because I think Conan would hate to see much time devoted to Leno in this, but the guy has proven himself to be an American treasure, as far as television and comedy go. I hope he gets the send-off that he deserves, because he’s just been really good for a really long time. And that’s hard.
What aspiring comedian wouldn’t want to intern for Conan? He can do all sorts of comedy: really smart, highbrow stuff and then really lowbrow, nasty stuff, but it still feels smart and quick. It was a dream to intern for a comedy legend.
I love that he goes totally absurd and surreal with a lot of his running gags. What other late-night host has a dog puppet insulting people? I love that he can be really crass and weird and still win over the hearts of the American public. That’s the challenge that most comedians try to achieve: How can you be unapologetically yourself and be super-weird and out there and still be loved by everyone? It feels like Conan bridged that gap. He brings people in with his smart, relatable observance of jokes that everybody can kind of get onboard with, then blindsides you in the best way with something really freaking weird. He makes his audience feel smart while still getting them to laugh at a bear jerking off.
I remember getting to talk with the writers, like Brian Stack. If you ever wanted to go get advice, they were always so welcoming. Of course, all your family and friends from back home keep asking, “Did you meet Conan yet?,” and I said, “No, he’s a frickin’ busy guy. He’s not wandering around the office, trying to get to know every college intern meandering around the place.” But one day, Conan held the door for me. He’s very tall, and I was standing almost right beneath him, and I just said, “Can I meet you?” And he was like, “Sure. Hey, how ya doing?” and shook my hand. He was so cool.
Then, at the end of my internship, he had a meeting with me in his office. I remember the essence and spirit of the meeting. Essentially, he told me to grind, like, “Make material and throw it up and don’t worry about if it’s good or if it’s perfect. Do shows and get up as much as you can.” All the comedians working there were shelling out material, day after day, and it didn’t always make it to air, but they still went for it. That’s part of the process of being a comedian, writer, artist, whatever; you’ve just got to generate stuff. It’s not always going to be good, but that’s how you find the good stuff: by not worrying about if it’s good.
Conan incorporates so many different styles, and he doesn’t really worry about what he is. He does sketch, he does stand-up, he does late night, and he does a bunch of weird shit. What I took from that was to not worry about categorizing yourself as a comedian; make what you think is funny, no matter what category people think it falls under. You don’t have to be any certain kind of comedian; you can be somebody who makes people laugh. That’s what America loves about him: He is unapologetically himself.
I started watching on day one. I was young when Letterman left that spot, but I was such a big comedy nerd that I was following the late-night story all along. It was exciting, and that first season was so meta. It was almost like he knew he wasn’t supposed to be there, so it was like you were on borrowed time. Which is almost what it feels like when you’re with Conan, because he’s so fast and funny. You feel, I just want to get the most out of this.
The funniest things were when he would have new recurring characters. I loved him driving the desk. I loved [Robert] Smigel doing the different politicians, when he would move their lips. When I moved to New York and started doing comedy, the people I wanted to be were all writers for the show: Jon Glaser, Brian Stack, Brian McCann. And he used to have Andy Daly on all the time and then Amy Poehler plays Andy’s Little Sister. Those are the people that I legit found at 19 years old and was like, I want to be like you. It was superspecial and important to me.
A lot of my meta stuff comes out of watching Conan. The biggest laugh of an episode could be a joke that bombs, but it’s the way that he delivered it that is funnier than anything that could have been written. That was a hugely formative thing for me: the idea that it’s not just the actual joke but it’s the context of the situation. And that’s why the Masturbating Bear gets a laugh — because it’s like, Yeah, if you put a masturbating bear in the middle of Times Square, it would be a crime, but if you did it on a late-night talk show at 12:30 on NBC, it’s funny.
I had several times in New York when I was asked to go to Conan when they were at 30 Rock and do a bit, play a character or something. It got cut most times. I had several appearances that never made it on television, but those were always amazing days because you get paid 400 bucks to be there. You’d get to sit in holding and watch the show, and that was truly so exciting. For a 22-year-old me, I was in heaven. I didn’t mind sitting in the hallway for five hours in an American-flag Speedo and getting cut. I got to see Conan, and Andy said hello to me — that was like winning the lotto.
Happy Endings’ showrunner is a super-talented, amazing, funny man named Jonathan Groff. Most of the cast at that time was more known than I am, so they started to book talk shows, and I didn’t have a publicist. I begged Groff to call and get me on Conan. And then when he did, I went further and emailed Brian Stack, like, “Can I do this bit where I’m in a tuxedo?” God, talking about it now, it was so presumptuous and borderline maniacal. But I said, “Can you run this by Conan?” And Brian came back so quick, “Yes,” that obviously he didn’t check with anybody. It was really, “You want me to go to Conan’s office and say, ‘Hey, the third guest wants to wear a tuxedo. Do you care?’” But the bit was actually really funny, and it worked. I always looked at those appearances like, If I ever get to do Conan, even once, I’m not going to treat it like an opportunity to talk about myself or whatever. I only have this many chances to do comedy. I think Conan, oddly, saw that in me.
One time, I did a bit where it was a very expensive makeup job, probably my biggest one. I dressed up like the Mask and Abe Lincoln at the same time. I had the teeth, the cheekbones, and the green makeup, and I drove there myself because I had to get there at noon to get all the makeup on. I was the third guest again, and I was clearly thirsty for laughs. And after, I got in my Prius and was driving out, and I pulled up at the gate, and right next to me, Conan pulled up in a pimped-out Tesla X with the wing doors. I still had green paint on me, and my car was all banged up. He rolls his window down with his sunglasses on, and he goes, “Wanna race?” I was so embarrassed. I also used to have an office above this sushi restaurant, and Conan would come in there a lot. We would often sit next to each other at the bar, and he would get really frustrated and angry with me because I would make him say hello to me. He’d be like, “Why didn’t you say hello?” And I’d do this bit where I was like, “I don’t know. I didn’t want to bother you. I didn’t know if you’d recognize me.” We kept that bit going for five years.
I can’t say I’ve had many deep conversations with Conan over this last decade, but I can say that we’ve had many, many comedic conversations, and we speak the same language. When you meet someone like that, you’re like, I am connected to this person for life. He’s exactly what you want your idol to be. I don’t care what he does next — I’m gonna watch it. And I hope to take a small part of it and make it about me.
I remember watching the show from pretty much when it started. I was a huge Letterman fan, so when Conan started, I remember being interested. And hearing that he wrote for The Simpsons, which I was a huge fan of — obviously, yeah, I stayed up late every night and watched. I had a little TV in my room, a terrible TV that I literally think we bought at a gas station for $5 that had rabbit ears, and it was on one of the channels that it picked up when I would lie in my bed as a kid.
It was something my friends and I really bonded over and loved. We would always do impressions of “In the Year 2000” and the Masturbating Bear. I think it was the first time I ever saw Amy Poehler on anything, her Andy’s Little Sister stuff. Triumph — we loved that. That was something we’d quote and talk about endlessly. I remember watching the show and feeling, He seems like someone who reads comic books and plays video games. He seems like someone who gets “this stuff” — the weird, obscure nerdy stuff that we were into.
It felt much more, I would say, “my generation” rather than the previous generation. The humor that he is partially responsible for on The Simpsons really shaped the comedic sensibilities of a lot of people who are around my age. When I started watching his show, it felt familiar in a way. It’s hard to classify — I would call it specific and referential and also very absurd by the standards of late-night television at the time. I’m Canadian — I was a big Kids in the Hall fan, and Conan’s stuff reminded me of that more than the other talk shows, as far as the big kind of swings it would take conceptually.
The lessons I learned when I look at his work are not being afraid to do stuff that, on its surface, might not be for everyone. But often, that stuff actually strikes a chord with way more people than you would think. I mean, he wrote The Simpsons’ monorail episode. I’ve seen the whole first 15 seasons, read enough books about The Simpsons, seen enough panels about people talking about The Simpsons, I wrote a Simpsons episode — and I’d say, almost unanimously, that episode is credited as being a tonal, defining episode for what the show became.
Over the years, doing his show has always been incredibly enjoyable. He’s someone who made himself available backstage, which was not necessarily the trait of all talk-show hosts, especially when I was starting out. I’ve actually felt like I got to participate in some of the sketches and the type of comedy that I grew up watching. That’s something I’ll always feel very lucky for.
It’s not something that is lost on me: that I’ve had these moments throughout my career where I’ve gotten to interact and create work, even in small doses, with the very people who inspired me as a young person. Every time, it feels special. It’s in the back of my head every time I talk to him: This guy wrote some of my favorite Simpsons jokes ever, even before I knew him from his work. And his SNL sketches … When you find out you’re a fan of something without knowing who did it, it’s surreal and thrilling.
I don’t know exactly what he’ll do next. Whatever makes him happy! You do you, Conan. I have no hopes for him beyond his hopes for himself.
In 1993, I was hired as a writer on Saturday Night Live, and that was his first year on air. He was in the same building, and everyone at SNL knew him. I didn’t, but that’s how I first was aware of him. At first, I was like, This guy’s weird. What is this? And little by little, I fell madly in love with the show. He brought this absurdist comedy that you hadn’t seen on a talk show. Also, you didn’t know the guy beforehand. Usually, it’s someone you know when they have a show. Talk shows are what people go to bed with at night, and they want it to be familiar, so it must have been hard those first nights, those first weeks, those first months, that first year to become a familiar face. But once it caught on, it became a whole new wave of late night.
Conan was a really new voice, and the staff he had was perfect: Jon Glaser as the tea copywriter or that weird floating head that would suddenly appear on the camera, Tommy Blacha’s Gaseous Wiener, and Brian McCann as the guy with bulletproof legs. It’s so dumb and then there was a several-episode arc with it, him getting shot in other places rather than his legs. So many times, writers on a talk show write for the host exclusively. I don’t know if it was the lack of ego, or the generosity, or the wisdom to also develop the writers themselves and the bits that they did. There were so many characters on the show that were born from the writers and their friends. He created a world.
Also, I grew up on Conan. Maybe you grew up watching Conan; I grew up on Conan. I was on it from when I was 22 to now. I’m 50 — that’s 28 years. God, I didn’t know who I was when I first went on. The first time I was recognized on the street was from being on Conan, because after I was fired from Saturday Night Live, he had me on all the time, doing bits from the couch. I felt comfortable enough there to try things on the couch and then later figure them out for stand-up, and usually it’s the other way around. But on Conan, it was so experimental. It felt so safe.
My favorite stuff is the dumbest stuff, and there’s an art to it. You can’t be dumb to do it. He expanded the rules. In a lot of ways, comedy needs boundaries. When you have total blue sky, it can be paralyzing, and he’s one person who found a million ways and directions to go. I can get kind of an attitude with Harvard writers, and he was one, but I just love his sensibility. There isn’t an elitist feeling in his work. He knows what it takes to raise other people up and have them shine.
When you look at his trajectory, it’s amazing and it’s frustrating. He did everything right. He made this totally unique thing that was every night, and he got The Tonight Show! That was the most bizarre, weird injustice: NBC not standing by him. It was fear-based. You can’t take Conan and be fear-based, not let there be big swings and failures. Then he went to TBS, and that show was great; he became less visible in ways, but he’s still so brilliant.
I hope HBO lets him do whatever he wants to do. You’d be shocked at how much someone has to prove themselves before an entity or network trusts them with comedy. So my hope for him — and for us, as an audience — is that they support any ideas and any things he wants to do, because that’s what we want to see. We want to see what he wants to do. Whether it’s more travel shows, getting back to more absurdist stuff, or narrative stuff, or specials — I just want to see what he does next, unbridled.
Conan was just kind of around for me. I didn’t really watch it that much. I saw it here and there because I didn’t really have a TV in the ’90s or 2000s. But I remember seeing clips and thinking he was really hilarious with some of the sketch things and bits he would do. He’s really fast, very quick-witted, and very self-effacing. Of course, his Irish Catholic–ness — I grew up Catholic, so I can get where that comes from.
He has a way of being a fake narcissist. He displays the traits of someone who’s narcissistic, but he’s playing a narcissist. And he’s also just kind of an awkward dude, and he recognizes that. He was goofy and silly and didn’t mind being the butt of jokes, which was refreshing. I put him in the same category as some of our great absurdists — and I consider myself an absurdist, so his freeness and energy definitely resonated.
Having me open for him on his tour, that was really where I got to learn a lot about him. It wasn’t really so much about comedy as it was his way of being in the world — the way he would interact with people and the fact that he never had security and was very grounded and very kind to people. I mean, he definitely razzed people and stuff like that as a bit, but that’s part of him being a loving individual. He cares about people.
When he started having me on the actual television show, they would let me do whatever I wanted. I’d ask for the stuff, and they make it happen. It’s very not complicated. I think I probably said, “I need something that says ‘Kwanzaa Juice’ on it,” they interpreted it, then I show up and there’s the thing I was talking about. I was always sure something would work out.
He’s a full-support guy. He’s there to make his guests shine — unless, obviously, they’re being assholes and then he’ll quickly rectify that situation. He’s very generous, shares the spotlight, doesn’t focus on himself. That energy is how I would do a show, whether it’s Comedy Bang! Bang! or The Late Late Show. I like it casual. That’s what that show felt like, and that’s the standard for our show now, because you want it to be laid-back and comfortable for guests.
I always call him a “good king.” He’s one of the few that has that power from being in pop culture for so long, and yet he stays super-grounded. He’s a really down-to-earth guy, the greatest example. That’s what I dream of when people get power. That’s what I want them to be like.