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'