Few would have predicted it from his 1993 debut, but Conan O'Brien has quietly become a late-night staple over the course of Late Night With Conan O'Brien's run. From a career writing for The Simpsons and Saturday Night Live, O'Brien took on the high-profile job of succeeding David Letterman as the host of Late Night. The show endured many troubles in its early years, but audiences eventually came around to its sensibility, a mix of self-aware talk-show conventions, absurdist humor, and relaxed interviews. Having weathered the departure of longtime co-host/sidekick Andy Richter, O'Brien's show seems as strong as ever. In a recent interview with The Onion A.V. Club, O'Brien reflected on what makes Late Night work and the odd course of his career.

The Onion: How do you decide whether a show went well?

Conan O'Brien: When I hear the laughs. To me, the best shows are the ones where unexpected things happen. Obviously, a good audience helps a lot, an audience that seems kind of sharp, but they're also just there to have a good time. Also, the best ones are when, either because something went wrong or because I found something during the show, it's very different from what I expected it to be. Or when a guest surprises you. It's a job to me, too, so I don't like it when everything happens exactly the way it's supposed to happen.


O: You get in a rut.

CO: Exactly. I always think audiences can tell when something organic is happening. When something, whether it's a guest mentioning something, or this weird moment, or there was a mistake and we comment on it, you get this energy that's very real, that you can't manufacture. To me, those are the nights when you really see me having a good time and finding things on the air. Those are the nights where I feel, "Oh, I shouldn't have gotten paid for that. That was just fun. I'd do that for free."


O: Some people believe that everything on a talk show is planned. Do you feel you have to play to that crowd?

CO: It's not so much that. It's that things are planned to a degree. To me, if too much is planned and it all goes according to plan, it's not fun to do. What you want is, you've got to have some idea of what's happening. You don't want Matt Dillon to come out and no one's ever talked to him, and we have no idea what we're gonna talk about and just go fishing, because too often the result is going to sound like a conversation you'd have with some stranger on a bus. Maybe there are interesting moments over 25 minutes or half an hour, but when you're talking to someone for seven minutes, you want to have some idea of where the interesting areas are. To me, I just prefer areas. I don't want a rehearsed story. I actually think when you get people to rehearse a story, it's no good. I think the much better interviews are… you want to have some area. Like, say Matt Dillon was a male prostitute in the late '70s, and that's how he earned money. If I know that in advance, and I know he's willing to talk about it, that's a good thing to have in your back pocket, because it's something we would have in common.


O: Otherwise, you get those awful moments where you have guests staring off into space telling the same story they've told on every other talk show.

CO: That's the thing. Our show, because we're on at 12:30 at night, we're obviously… We're coming behind these 11:30 shows. In a way, you've got to work that much harder. I'm not the first person Billy Crystal is talking to about his new movie, so a lot of times you have to make a strength of your weakness and do something with him that nobody else has done. Otherwise, you're right: Why watch my show if you've already seen the same story on Dave or Jay? So that's why we always try, even if that means pouring hot tar on them. It's got to be different. So, half the time, what we do usually ends up hurting the guests physically.


O: When you find a bit like Triumph The Insult Comic Dog, at what point do you know you've got a keeper?

CO: It's the first night. You don't know how long it's gonna last, but you know the first night, "Oh, that's coming back. We'll be seeing more of that." We were always real concerned about running things into the ground early on, so we would phase things out. Like, we phased out PimpBot pretty quickly. I used to walk around New York, and all these college kids would be yelling out, "More PimpBot! Where's PimpBot?" and I would think, "What did we phase that out for?" We were too worried about running it into the ground. We were so worried that I think sometimes we almost did ourselves a disservice with some things. With Triumph, we made a decision not to do that many. He's only on once every couple of months, which is one of the reasons he's lasted longer than a lot of things. I think there are a lot of shows where, if they had found something like Triumph, he'd be a feature every night. "It's quarter to one, so it must be Triumph Time." I think that's when people are like, "Forget it. I'm tired of it."


O: Have you gotten tired of any bits that are too successful to get rid of?

CO: There are some bits. We're aware at the show of the things that are less interesting and creative than some of our other bits. There are things like "If They Mated," which, we're not kidding ourselves: We know that it's just funny pictures. But we make a lot of shows. We're on every night except for the weekend, and so every night you can't always do your favorite bits. And it's a bit that audiences really like, and it's an opportunity for me to ad-lib. Is "If They Mated" our favorite bit? No, it's not. But it works. And we try not to do it too much, so we do it every now and then, but not every night. Not every night can just be a grab bag of new characters, or something that involves actors and camels in flames, because it's just too expensive, and it grinds everybody into the ground. We do a lot of jokes about how the show is low-budget. We're on at 12:30, and because my personality is very self-deprecating, the show has a self-deprecating air about it. But we do occasionally, and actually not so occasionally, put a lot of effort into something that's just seven minutes between 12:40 and 12:47. Like movie reviews, or bits like "Guests We'll Never Have Back," where we're staging really complicated scenes, and we're using firearms and squibs, and we're rigging blood packs, and we're shooting it all day long, or we're shooting it for like four days before we do it. You put all this work into it, and then you get it just right and it's seven minutes long. A hardcore fan of our show, if such a thing really exists, maybe sees us twice a week. That means they're gonna miss that bit, probably. That's the kind of thing that's always eating at you. You have to put so much work into some of these bits that every now and then you've got to drop back and do a "Children's Drawings" or "If They Mated," or something we're not completely grinding ourselves into the ground to get done.


O: On the other side of the coin, do you ever repeat a bit that didn't work the first time, and hope it might go over better a second time?

CO: Yes. Yes.

O: Does it work?

CO: No, never seen it happen.

O: Can you give an example?

CO: What's a really good example? Let me consult with the writers. [Consults with writers.] We did this bit once where we just said, "Ladies and gentlemen, please welcome Rev. Otis K. Dribbles," and in the performance area we just cut to a guy dressed as a priest and wearing a dog mask dribbling while "Sweet Georgia Brown" played. It made us all really laugh at rehearsal for no reason, and we did it, and people didn't laugh. But the writers brought it back, and I don't think people laughed again. And then I think they were like, "No, we've got to try it a third time." I think we tried it a third time and it didn't work, and it was like… On the show, there's this really delicate balance between pleasing ourselves, just making ourselves happy, and making the audience happy. And I think for a good show, you have to hit this balance, because you can't just completely appeal to the audience. You have to do things that just make us laugh, because you have to lead a little bit. But that was one where it was definitely, "Okay, stop this." Another one we tried a few times was "Seven Foot Groucho." We got a black guy who was seven feet tall, and we dressed him up as Groucho Marx, and we'd introduce him and he'd come out and go, "That's the craziest thing I ever hoid!" He'd have a Groucho moustache, but we picked him solely for his physical presence, because he was seven feet tall. And he did a horrible Groucho, and no one got the… There was nothing to get. We've done some really great stuff on the show. It's not all just about jokes. Some of the best stuff we've done has been visually strange, and people laugh, but they don't quite know why they're laughing, because it just hits some nerve. So you always have to be willing to try. I think the quality about the show that I like, that I like about the writers and the spirit of the show, is that we do try stuff. When you demand that things work 100 percent of the time, you end up with a mediocre show, because you can always do certain jokes that will always get a laugh. If you're doing that 100 percent of the time, the show won't be that interesting. Whereas if you take a chance, and do some strange stuff, and use puppets and animation, or let there be weird moments or try things, it's not always going to work. But when it does work, it has such a big payoff that you get people to come back, because that's the kind of thing that people talk about the next day. "Did you see that last night? That was really weird." That's the theory, anyway.


O: Do you think the studio audience is always the best gauge for what the TV audience…

CO: No. There are nights when the audience reflects the core audience at home. Sometimes the audience is a pretty good representative, and if something is too mean or crass, or just too lame, they won't go for it. In a way, you're finding out, "Yeah, we did go too low," or "That was too obvious," or "That was sort of a hack-y ending." Then there are some nights where you're doing stuff you really like, but there's an audience that's not very demonstrative, or there's an audience that you don't know what their problem is. I've seen audiences sit there and not really laugh at anything, and then after the show, they're all waving at me and smiling as I walk out the door, [saying] "Oh, man, that was great." And they're just not… They're intimidated, because it's this TV show, and they don't know what they're supposed to do. There are other audiences that are too frat… I get depressed if I do a joke that has something to do with alcohol or pot or something, and a whole audience of 20-year-olds with backwards baseball caps goes, [adopts low voice] "Yeah!" I feel my soul leaving my body.


O: It's no good pleasing people you don't like.

CO: Well, I don't want to say I don't… I don't want to be harsh. It's more like I like to get a laugh, or not get a laugh. There's this phenomenon now in America of just, "Yeah, woo!" People go "Woo!" If you ever watch Total Request Live, everybody does that. It's a phenomenon that depresses me. I think it's partly daytime talk shows like Jerry Springer and stuff. It's encouraged on so many shows. "Woo!" It's encouraged, so all they know is that when they want to be part of the show and they're having a good time, they want to "Woo" in the correct spot. They're not really listening. So they wait until after I'm done with a joke, and then they go, "Woo! Oh, yeah!" It's kind of not why I got into comedy. If I wanted that, I'd have become a jai-alai player or something. I like an audience that's listening and then laughing or not, because if they listen and then don't laugh, I can usually have fun with the fact that they didn't laugh. Or I can play with the fact that I failed. That's fun, because that's just reality that people respond to. "Oh, look, the professional comedian/talk-show host is in a little bit of trouble out there." I think people like to see me work my way out of a situation.


O: It's honest reaction versus a Pavlovian reaction.

CO: Exactly. But when you're out there and they just hear, "I don't know if you heard, but a woman in San Antonio was arrested with 800 pounds of marijuana in her truck…" "Yeah! Woo!" I get sad, because I think, "Oh, I'm just the host of American Gladiators." There are crowds that think you want a standing ovation or something, because they see that on other shows, and they think that's what you're supposed to do. The ladies of The View get a standing ovation every day on their show, and I think, "How much have we devalued the standing ovation? That's just ridiculous." Johnny Carson got one standing ovation, the last night he did his show, and it was really cool. It was like, "Wow, he did 30 years and then ended it on a classy note, and he got a standing ovation." And then you realize that Maury Povich is getting a standing ovation every day on his show. I don't like that. I don't like that stuff. Sometimes I think audiences are too… They've picked up bad habits from watching these things on shows. I like people to just be honest, and if I'm funny, laugh. If you're not so sure, don't laugh. I'll try and win you back. But let's have it be honest. If I wanted to get "woos," I'd have become the dictator of a South American country.


O: At what point was the decision made to bring in Abe Vigoda?

CO: It's called making your weaknesses strengths. When we were starting out, we couldn't get… David Letterman on CBS, back in '93, was such a big deal that he could have Tom Brokaw run out and throw crackers at the audience. He could have anybody walk on. He could have J.D. Salinger come out, pour fudge on himself, and do a dance, you know what I mean? And we were a new show, so we would have to sort of be creative about finding people. And at the time, Abe Vigoda was the guy you didn't really see. Everyone knew who he was and liked him, but hadn't seen him around. So we had him on the show as a guest, and then we started using him, and we realized he's got this great face and really good comic timing. It was a happy surprise. He became this person of ours, so we started developing our own repertory company of Nipsey Russell and Abe Vigoda and the Masturbating Bear. It became our own over time, and became part of the identity of the show.


O: Do you think people have forgotten the difficulties you had early in your career?

CO: You know what, it's funny. Definitely. Four years ago or five years ago on the show, I could have still gotten a laugh from, "Oh, my early days were a piece of cake." Everyone would laugh, because they would still kind of remember. What's fascinating is that young fans have no clue. I spoke at U Penn a couple years ago, and I started telling the kids about our early reviews, and reading really mean things they said about me and Andy, and the audience was like, "What are you talking about?"


O: They weren't around then.

CO: They weren't around, and to them the show is this established old chestnut that's, "Ah, that old…" They grew up with it. There are kids who started watching it in high school, and now they work for me. I ask them, "When did you start watching it?" "Oh, I was a freshman in high school." "I was a sophomore." "I was 16." And now they're working here. I gave this speech at Harvard last year that got sent all around the Internet. I had a lot of jokes in it, and then I tried to make a point by reading them the meanest review that anybody wrote of me, because I wanted them to understand. I think all of them saw me as just… Once people get established and have success, people tend to think they were always like that. The most important thing you can tell young people is that there's this process, and it's never over. You never really feel like you've made it. You never really feel… There's a lot of difficulty getting anywhere, and once you're there, you never feel like you're there. I'm always feeling like, okay, now we've got to get this show to the next place, whatever that is. If tonight was a good show, we've got to try really hard to make sure tomorrow's a good show. If tonight was not a good show, I'm depressed. I'm as depressed as I was seven or eight years ago when we had a bad show.


O: That's probably a healthy approach.

CO: I think so, yeah. I think it's just the way everybody feels about their work. I think that's been a good quality the show has had. It's always had a humble attitude about, "Let's really try and do a good show tonight."


O: Do you think you brought the show around, or that people came around to the show?

CO: I think it's both, because I think with the writing, it's people coming to us, because the writing was always there and always, I thought, pretty strong. If you go back and look at a tape of the first show on Sept. 13, 1993, it's a good show. What wasn't as strong was, I hadn't figured out a way to be myself on TV yet. I hadn't figured out a way to be Conan O'Brien completely. If you went back and looked at an old show, you would see, "Oh, yeah, that's Conan, but he's not… He's a little more rigid." I was real earnest and trying to do a good job, which nobody really wants to see. To answer your question, I think people came around to our sense of humor, but initially, I don't think all the criticism was wrong. Maybe in the severity, but I wasn't nearly as good a TV performer as I am now. I got a lot better, and I learned how to just be myself and do all that, whatever, muttering, and those asides, and make those observations. I learned how to just do that and be the way I am with my friends in a very unnatural situation. I think that's the part of doing these shows that no one understands. The trick to them is not to become a funny guy. You have to just be that from the beginning. The trick of these shows is figuring out how to be the person you always were in an unnatural situation, with five cameras staring at you, and with an audience sitting there, and lights, and celebrities you've never met coming out.


O: When you have someone on whose work you just don't respect at all, how do you deal with that?

CO: We won't name names. You can usually tell. I'm just a little more reticent. If someone's being really hack-y, you can just tell. I think if you watch the show a lot, you can tell. I take the title "host" seriously. I'm there to try and show these people off at their best, not rip them apart. And we've invited them, so I'm not a big believer in, "Let's get Carrot Top in here and rip him a new asshole." If you have someone here, just find what you like about that person. Find what you think is good about that person, and try to get to that. If there's someone whose work I really don't like, I probably wouldn't have them on the show unless they… Sometimes it's a really big star, and you've got to have them on. I think you can probably tell. I'm not a really good liar, so I'm not going to stand up there and say I think someone is the greatest genius in the world if I can't stand them. I'll just try and find what I like about that person.


O: It would spoil the mood you've created with the show.

CO: Yeah, the mood of the show is very much… I don't know. One of the best observations about me I ever heard was, a long time ago, some reporter was calling friends of mine to ask about me, and they got hold of one of my college roommates. And he said, "Conan's funny with people. He's not funny at their expense." That's not a moral choice; that's just how I've always been. Hey, if I was a really great insult artist, and I was really good at ripping people apart, I might be doing that, but it's just not my… If Fabio comes on, try and have a really fun time with Fabio. Yeah, I'll walk the line of giving him a hard time about his man-boobs or something, but… I'm not going to kiss their ass, but at the same time, I'm not there to judge them. I don't actually feel better than these people. We're all making a living somehow, so I don't know. I like to have a really funny interview with Fabio, but not at his expense. I think that's part of the mood of the show, which is a really silly, weird show. It can be mean-spirited at times, but I don't think that's us at our best.


O: How seriously did you consider bringing in another sidekick after Andy Richter left?

CO: Well, we really didn't know what we were gonna do.

O: He gave you plenty of time.

CO: Yeah, we knew like a year beforehand, but I remember thinking, "We can't do anything about this while he's still here, we just can't. It's just not right." I don't want to be like, bringing in other… Like, "Oh, Andy, this is Chip. He might be the new you. This is Chip Wexler. Andy Richter, Chip Wexler. We're just measuring him for the sidekick chair." [Imitates Richter's voice.] "Oh, hi, Chip." That would feel weird. I just thought the best approach is the honest one, which is, "Let's enjoy Andy as much as we can while he's here. And then, let's not even think about what we're going to do until after he leaves. And then, if someone really good comes along…" The Andy decision was an organic one. We didn't set out to have a sidekick, ever. I just met him the summer I was putting the show together, and he seemed really funny. He just seemed perfect. He's really funny, and he kind of looks like a young Ed McMahon, and this would be this new thing of a sidekick who's not just there to laugh at stuff I say. He's there to give off his attitude and be funny in his own right. He's a good improviser, and he's a actor, so he can really commit to bits. Like, if I get shot, he can really cry and act like I've been shot. He's not winking at the audience and fake. Finding Andy in the first place was this organic thing, so I thought, "Only replace Andy if somehow I meet or come in contact with this really great person. But, if not, let's not force it. I'm not going to marry somebody else just because the first wife I really loved passed away." See, I've made it sexual now. Andy was my wife. That was the idea. And I remember saying, "The major point is, I'm not going to replace Andy Richter with somebody who's not as funny." So we started getting the show off to a faster start, and I use the audience more, and I'll sort of talk to the camera about my life, but usually just get right into something with a smaller piece of comedy. It's changing around a little bit, just to make it different.


O: Pretty soon, you'll have fans who don't remember Andy Richter, too.

CO: I don't know if that's possible, but I like… The thing that I've liked the most is that Andy is still part of the show, because he still lives in New York, and he'll come by, and we're still all really friendly. He was here last week at rehearsal, and he was sitting next to me and making jokes, and it was really great. It's not some weird show-business thing of, "Oh, my God! Dean Martin and Jerry Lewis are in the same room."


O: Did you always want to be a talk-show host?

CO: I never really knew. It was more like process of elimination with me. I knew that I'm not an actor. It wasn't something I was ever that interested in, like going and getting a head shot and reading stuff that other people wrote. Stand-up comedy… I never wanted to just memorize a routine and tell it to people. I admire stand-up, I admire what they do, but I always thought what I like is much more interactive than that. Which is why I did improv for years in the '80s. That's kind of the thing that got me into performing: It could use my writer's head, but I could also get up in front of people and be physical. It was more just process of elimination. I never really knew what I wanted to be until… I remember in the '80s, when I was in college, staying up late and watching Letterman, and just thinking, "Oh, that thing he's doing…" I didn't think I could ever be as good as him, but I remember thinking, "I could do that kind of thing," where you get to tell a couple jokes and do stand-up for a second, but then you can also present really weird comedy, which was something I always liked. But you can also talk to people, and improvise, and try and be spontaneously funny in an interactive way. You can have cool music on. And it just hit some nerve with me. I used to talk about someday having a show, when I was in college, and I used to tell people about my show, and "Someday I'm gonna have a show." I'm sure a lot of people do that, and they seem delusional. But did I ever expect that Letterman would leave, and through 50 crazy events I would replace him? No, I wasn't that crazy.


O: It was very odd when you were named.

CO: It was just… I've had certain people credit me with being a genius for manipulating events so I could get the show, and I'm not that smart. It was literally a series of events that could not be duplicated. I was very, very lucky. I think, in retrospect, that I have some ability in this area, and I'm glad I got to do it, and I think I've done a good job, but to this day I still can't believe sometimes how I got the job. People ask me, "I want to do what you're doing. What advice can you give me?" And I just think, it's like you're asking someone who got hit by a meteor, "I want to be hit by a meteor, how do I do it?" I don't know. I was walking in a field and the meteor hit me. I don't know what to tell people. I was very fortunate.


Andy Richter on Conan O'Brien
Andy Richter: He's a brilliant man. He's a brilliant, brilliant man who I hope doesn't become as fucked-up as other talk-show hosts. Because there's something about that job that seems to make people weird. There's a part of doing that job that really makes him happy and is very fulfilling, but then I think that that fulfillment seems more substantial than it actually is… But he's happy doing it. I just was by there. I'd been in L.A. for six weeks, and I came back home [to New York] for three days, and his birthday just happened to fall on one of those days, so I went and hung out there. I was just talking to somebody about how glad I was to see him, and they were asking if I miss doing the show in front of the audience. I was like, "Hell, no. I don't miss performing for tourists, most of whom are mad that we're not Rosie. I don't miss that at all. They're despots, those studio-audience people." And Conan was saying, "I still love it. I still love dancing like a monkey in front of people who came in on a bus." He really, truly is a rare mind. He has a wonderful, wonderful comedic mind.