Conan O’Brien, Tina Fey, and More Share Their Favorite Letterman Memories

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Tina Fey takes off her dress after her last appearance on Late Show With David Letterman. Photo: John Paul Filo/CBS

In honor of the final Late Show With David Letterman Wednesday night, we surveyed a number of cultural figures on their favorite Letterman memories, both on and off the show. "Stupid Pet Tricks" and Chris Elliott's man under the stairs were crowd favorites, while some couldn't pick just one, choosing instead to reflect on his legacy. Most could agree on one thing, though: It's really freaking cold on the Letterman set.

“I went through my whole process of discovery with him, but it all really went back to that first time I saw him. I watched his morning show. It was such a different experience. To me, that was the seminal moment, seeing him for the first time. That’s what really changed everything. He had such a huge impact for all the comedians of my generation. The show was so different from everything I had seen on television before. It was very intimidating to meet him for the first time, I believe it was 1993. I’ve met a lot of celebrities, but every now and then you meet someone who’s had a real impact on the culture, and that’s a different experience. There’s a couple of people who fall into that category where you meet them and it’s like meeting a Beatle. They really altered the molecular structure of the society in some way. I’ve always had a great respect for his work. I was on his show. He was one of my first talk-show appearances back in 1993, he had me on when he was on Late Night. There’s no meeting Dave in the green room. [Laughs.]  That doesn't happen. He’s like a magician; you only see him onstage. It’s just the way he prefers it.” —Conan O’Brien

“The thing about doing Letterman is I'm always so happy right when the segment is done because I always get super, super, super nervous. Then I spend the next month thinking about what I did wrong and how I could have done it better. And so now that I've done it the last time, I'll keep remembering my mistakes from that segment for the rest of my life. I think, I didn't do this and I didn't do this ... He's the king, so everyone wants to do well.” —Tina Fey

“My favorite memory of David Letterman is the fact that when everybody was leaving New York, he stayed. That was in the bad times. That was before I was the mayor. That’s when we were on the front cover of Time magazine as 'The Rotting of the Big Apple.' That’s when, remember, Johnny Carson moved The Tonight Show to California. We couldn’t get a movie in New York. They were filming New York in Toronto. And Letterman’s staying, I always thought, helped the city a lot. That’s why whenever he asked me to go on the show, I never refused him.” —Rudy Giuliani

“The first impression he made on me was on his morning show — remember his morning show that was short-lived? I would watch that, and I think it was when I was in college, and I had never seen anything like that. Those shows were usually cooking lessons or something like that. And he’d have guests on, and you’d realize, ‘Oh! These are fake guests!’ Like he had somebody who told jokes by chewing, so they were like a food comedian or something. That was the first thing I saw him do. He’d say, ‘Tell us a joke,’ and the guy would chew on a piece of carrot, and Letterman would laugh, like the punch line had been hit. That was the moment I was like, ‘Who is this guy? He’s hilarious and subversive and funny.’ And then when his nighttime show came on,  that was another kind of religious experience. He was doing something that Johnny [Carson] or anyone else wasn’t doing, which was having a true interaction with the audience at home. I always credit Letterman for that. His opening monologues wouldn’t even be that great. The jokes were always kind of weird. I always felt like he brought in an audience that kind of didn’t get it. So what happened was, he’d tell an odd joke, you’d think it was hilarious, the audience in the studio would have a weird reaction, and then he’d look directly into the camera, like you’d think he was saying, You and I know this is funny, and the people here don’t get it. You know, when you’re doing stand-up, the laughs you like the most are when you hear your fellow comedians in the back of the room crack up, and that to me is what the Letterman show was. You want to make the audience laugh, but when you can make your peers laugh? That’s the greatest thing ever. There was a ten-year period of my life where I could not dream of going to bed without seeing Letterman. I had to watch the Letterman show. It was not a choice. It had to be done.” —Paul Feig

“I was on Letterman once, a long time ago, when I had made The Abyss, so that would have been ’89. And he was kind of a jerk. I mean, the second the camera cut, he wouldn’t talk to me. He turned away. So I said I’d never go on the show again, and I never have. I mean, every time I make a movie, they want me to go on Letterman. But it’s like, ‘Why would I want to go on the guy’s show? He’s a jerk.’ Ugh.” —James Cameron

“My favorite Letterman memory was that he told me, ‘Hit the seat running.’ And I thought that was great advice. Just hit it running and sit down and start going. I was really nervous. I heard he was a pretty tough guy, but he was pretty easy on me. And he was actually very friendly, so I had a great time. I would say the Cher interview is my favorite. When he asks, ‘Why haven’t you been on my show?’ and she said, ‘Because you’re an asshole.’ I would say that.” —Steve Guttenberg

“There was something in Vanity Fair about the death of irony — when the World Trade towers came down — I think it was the death of a lot of people, not the death of irony. But  David Letterman, his ironic attitude, was something that I found very appealing. One of my comedy heroes was Paul Krassner, the editor of The Realist back in the day. He was an underground comedy writer, and he said that his job as a humorist was to point out that the emperor wasn't wearing any clothes. Not to say that the emperor should be wearing clothes. But just simply to state that he's not. And I always identified with that and thought that was good. I think that was always a Dave Letterman and Jon Stewart characteristic. We'll see what happens in the new millennium.” —Anne Beatts

“David Letterman changed my career because he gave me my break. My first late-night television spot was on Letterman. His booker at the time saw me do a spot in the Village, and she asked me if I wanted to come do a spot on Letterman. It changed my life because I started getting college bookings after that. It was an amazing moment. It’s bittersweet. Dave’s the best.” —Dane Cook

“I’ve only been on the show once, and it was my first-ever late-night talk show. It is so cold in the studio. It’s like the most freezing place I’ve ever been. I remember being really nervous and knowing that if Letterman didn’t like me, it would be like crash-landing awful. But I remember making him laugh and feeling really good that I had made him laugh. Because I felt like, The rest of this is going to be smooth sailing. Not just the rest of the interview, but the rest of all of my interviews forever would be smooth sailing. I was telling him about how I worked for a knife company, Cutco Knives, and they were like, ‘You have to sell it to your friends and family.’ And the first person that I tried to sell it to was my best friend’s mother, but I couldn’t stop crying during it. And he says, ‘Well, that’s a great way to sell. That’s the ABCs of salesmanship.’ And I said, ‘Yeah, always be crying.’ And he laughed! Now that I think about it, I think that’s what he was going to say, but I think I stole his joke out of his mouth. That’s probably why he hasn’t talked to me in years.” —Gabourey Sidibe

“I was thinking about him the other day in the shower. [Chuckles.] I was thinking about the fact that his show is coming to an end, and I was thinking through my formative years when he was on NBC and then on CBS. He really played such a huge role. He was so influential to so many people. He was the king for our generation. The novelty never wore off for me.” —Will Arnett

“I remember when I was a kid, we used to cut school and watch David Letterman. We’d watch David Letterman during the day and we’d be like, 'This guy is weird,' and then all the sudden he’s on late-night.” —Adam Horovitz

“In all these years, and I’ve been doing [Letterman] since 1995,  he never came to see me in a show in New York. Not even The Producers. You know, he doesn’t really care for the musical form, I believe, musical theater. But for some reason, Bill Scheft, a comedy writer and friend of his, at the show, said to me, 'He wants to come see you in the David Mamet play November.' I said 'Well, great.' He said, 'Yeah, I’ll let you know when, it’ll be a last-minute thing.' And so he calls and says, 'We’re gonna come Wednesday night.' And I said, 'Oh, don’t come Wednesday night. Wednesday nights are notoriously bad.' And I said, you know, and the play got sort of mixed reviews, so … But anyways, I said to the theater, 'Just fill the house, just get people in there. Make sure it’s full. David Letterman is coming!' So we start the play, and we always knew how the play was going to go by the opening lines, which was me saying to him, 'We’re losing points in the polls and we don’t have enough money for something,’ and I say, ‘Why is all this happening?’ and he would say, ‘Because you’ve fucked up everything you’ve touched.’ So if people didn’t laugh, we knew we had a long night ahead of us. There was dead silence. And then I heard two elderly women arguing over a headset. At the end he came back and it was like Elvis arriving. He came flying into the room and couldn’t have been sweeter or more gracious. We just sort of sat in my dressing room for about five, ten minutes and chatted and then he finally said, 'Well, I’m sure you want to rinse out a few things before you go.' And then he left. But he couldn’t have been sweeter about the whole thing. That was a very long story, and I’m not sure the payoff was worth it.” —Nathan Lane

“Anytime he has the NBA finals champion team on the show. You never know what you’re going to get with those guys, so it’s always good.” —Victor Cruz

“The first time I was on David Letterman, the night before, Billy Idol was on. And the interview went something like this. ‘So, Billy, you got a big hit record.’ ‘Yep.’ ‘So, how are you enjoying the United States?’ ‘Pretty nice.’ ‘Yep.’ Nope.’ So, I got on the next night, and I think David was pretty concerned about the pace of the interview, so we went back and forth pretty fast. I had to prove to him that I could put together complete sentences.” —Glenn Frey

“I remember watching Letterman at our neighbor’s house. One of my first friends ever. I would stay up, and what I remember about him more than anything is how normal and real he seemed, like one of us. But [my favorite was] when he and Paul Newman were racing in the cars. He and Paul had such a great relationship, so that’s always been such a huge, huge thing for me.” —Theo Rossi

“He was really the Johnny Carson for my generation. I got to do a top-ten list, that was so much fun! I still have Paul Shaffer singing my arias in my key on my cell phone. The quirkiness of Letterman is what I liked. And yet you could tell he liked people and really enjoyed what he was doing. All of those kinds of odd things that he did before quirky became the norm. Now it's the norm, but when he started it was just, Wow. Where is this guy's brain? It's like he's on another planet. I loved that.” —Renée Fleming

“His first season, I couldn’t believe that Letterman had a show. I knew what he was beforehand, and everything from that first season was just magical for me.” —Larry Wilmore

“As a kid, I was a big Letterman nerd. I had a big crush on him. Now, I have two little kids, so I don’t make it up that late anymore. So on my bedroom wall — and this was in the age of Teen Beat and Tiger Beat or whatever — I had Harrison Ford, this great picture of David Letterman, I think from GQ, and Pee-wee Herman. Those were my hunks. So that just goes to show you I don’t really have a type! Combine them and they’re the perfect man. You’ve got the brains, the Harrison Ford swagger, and then you’ve got the Pee-wee Herman adorable wordplay cutie-ness. Bring them all together in the same room, and tell my husband to watch out — it’s all over.” —Gillian Flynn

“In his original show, when Gene Shalit is sitting in the seat and being interviewed, and Letterman says something like, ‘Cut the giant hammers,’ and they cut to two crew guys in the back and they say, ‘Did he just say, "Cut the giant hammers?"' 'I think he did!' and they cut a rope and two giant hammers go smack into Gene Shalit’s head.” —Rory Albanese

“When Brian Williams went on and told his story about the helicopter. You know what I love about Letterman? I feel like he is the master of feigning interest while also still not looking interested. He’s just such a pro.” —Robin Thede

“My favorite Letterman moment was when he did a Stupid Pet Trick where there was a guy who had a dog, and he put money in a paper bag, and the dog went and bought beer for the guy. He would send the dog to the store, the dog would buy beer, and the dog would come back with beer and the change in the bag. And it would be the right kind of beer! There was a whole situation happening. It was great.” —Lizz Winstead

“When Will Smith came on and he was like, talking about his thighs. It really made me laugh. And then when Jay Z was on and he was giving the minimum amount of information about his marriage. I thought that was hilarious.” —Jay Pharoah

“Letterman was who I idolized when I was young. The first thing I started doing when I was a kid was I would pretend I was David Letterman and do school assemblies where I would basically just steal his top-ten lists and read them to the class. I don’t know if they were appropriate for fifth-graders at the time. I would get all my classmates to act out bits we saw on that show or SNL. So he was the first person I kind of looked to as, oh, I want to be that guy.” —Colin Jost

“Paul McCartney’s really funny, and Letterman was like, ‘Why haven’t you ever done my show?’ And he was like [high British accent], 'Because I don’t like your show.' It was just the way he said it that made me laugh, and it’s fun to watch Letterman because he’s been doing it forever, so it’s nice to see him not care. Not not care, but he’s so free with everybody.” —Pete Davidson

“God, so many. 'Stupid Pet Tricks' was always a favorite. I was a big Larry 'Bud' Melman fan, in the early stuff. When I did the show, the most indelible memory was how absolutely freezing it is on that stage. He likes to keep it fast, and it hits you like you’re walking into a forest or a butcher shop deep-freeze. And it worked: It kept the gab running. It was probably a little earlier. Maybe it was around Titanic.” —Billy Zane

“I’ve always enjoyed it when John Malkovich was on the show. That’s probably when I’d watch. [Letterman has] always entertained me, and I found him an affable, intelligent, subversive, wry character.” —Julian Sands

“[I remember] how incredibly freezing cold his studio is. It’s horrible!” —Patrick Stewart

“I used to watch him when I was a kid in my bedroom. I had a TV in my bedroom, and I used to dream of going on there. And this is my teen humor, I was like, ‘Dave, I know that’s not a real skyline behind you.’ And then we’d do a musical number together, outside with the real New York skyline.” —Missi Pyle

Velcro wall. That was the first time I was like, 'I have to keep watching this show,' when I was young. He used to do really daring, weird stuff that other shows still don’t do. Like just walk out onto the street and interview people. Like he didn’t care. He established what Late Night was. There was no other structure for it, no precedent. And he really went there in terms of like having on wrestlers and, I mean, he had so many clips that I think were never even aired, where Crispin Glover punched him in the face. He really established the sense of, there’s another kind of talk show where things don’t go right.” —Seth Herzog

“A long time ago, Chris Elliott would do guest appearances on the show. I remember him singing a song about bananas and coming out from under the stairs, I believe. Just I loved all the crazy Chris Elliott stuff.” —Chris Parnell

“One of my favorite memories is probably Chris Elliott doing Brando and Chris Elliott doing man who lives under the stairs. Those were some of my favorite bits ever.  I love Chris.” —Tim Meadows  

Larry 'Bud' Melman was always a great one. That was like the beginning of, ‘Hey, we’re going to get some weird regular people on and make them stars.’” —Colin Quinn

“My favorite Letterman memory has to be when I did Letterman. I got to do stand-up on Letterman, and it was a huge honor because David Letterman is a pillar of comedy judgment. So, if you get a gracing from David Letterman, you feel like you really did something.” —Michael Che