Late Night With Conan O'Brien experienced one of the most dramatic reversals in recent pop-culture history when it morphed from a near-fiasco to a critic's darling and popular success. Perhaps it's fitting that O'Brien's early career alternated between huge successes and public failures. Twice elected president of the Harvard Lampoon, O'Brien graduated from Harvard and moved to Los Angeles, where he wrote for Not Necessarily The News and The Wilton North Report. He also performed on the latter, though it was notoriously short-lived. O'Brien rebounded as a writer for Saturday Night Live, the writer-producer of the Adam West detective-show pilot Lookwell, and a writer-producer for The Simpsons.
O'Brien was still largely unknown to the public when his old Saturday Night Live boss Lorne Michaels unexpectedly picked him to succeed David Letterman as the host of Late Night. O'Brien's early years were famously rocky, but the show steadily evolved into an oddball delight. When Jay Leno announced his planned retirement, O'Brien was named to replace him on The Tonight Show as of 2009. While preparing to host the Emmys (which air Sunday, August 27), O'Brien spoke extensively with The A.V. Club about his colorful early misadventures in show business, taking over The Tonight Show, and the oft-overlooked upside to agonizing failure.
The A.V. Club: At the first show you did in Chicago, there was a five-minute standing ovation when you came on. What's it like to experience that?
COB: I like to live my life like I'm Mussolini. That always ends well. Hung upside-down with your mistress in a gas station. But, no, it was really fun. There was such a nice feeling in that room, because people were enthusiastic, but they also sort of listened to things. They seemed to be paying attention to the comedy, which was good.
AVC: Does it rejuvenate you to take the show on the road and get a change in scenery?
COB: Yeah, Cincinnati is where I'm hitting next. Raleigh, North Carolina. What I want to do is just malls. It's a mall in a city no one is thinking about. It's a surprise Late Night with confused heavy people.
AVC: It worked for Tiffany.
COB: It's following the Tiffany model.
AVC: Tiffany and Mussolini are your two touchstones.
COB: Well, think about it. Both of them had their own talents. Tiffany and Mussolini have never been mentioned in the same sentence. I'm thrilled we've achieved that. If nothing else, we have that.
AVC: You'll be taking over The Tonight Show in 2009. Will that give you enough time to prepare?
COB: I asked them if 2015 is possible. It's like a term paper. It's like calling your professor the night before, and saying your mom is sick. I'm going to call NBC the night before and say, "Can we make it 2015?" I'm going to keep trying to get an extension over and over again until it's around 2020, when the president of the U.S. is an aluminum cyborg. I think that's the appropriate time to take the 11:30 slot.
AVC: How did you find out about the Tonight Show gig?
COB: Ed McMahon came to my door. It was shocking. He had a large check. And he seemed confused. I don't think he's well. He had two medical attendants with him saying "No, Mr. McMahon, no. Finish your pudding." I got the call that NBC was curious if I was interested, so I said "You betcha!"
AVC: Will you be doing The Tonight Show from New York, or L.A.?
COB: No one said specifically. The Tonight Show has been in Los Angeles since 1972. So someone please do the math. Upward of 30-something-odd years. It's such a strong franchise that I can see them maybe feeling like the mountain doesn't go to Mohammed. I should get my ass out there to L.A. I can see it going that way, but no one said specifically. Which is why I keep pushing for Tampa.
AVC: Do you think you'll be able to do the same show an hour earlier?
COB: I don't know. I look at our show sometimes, and I don't know what the appropriate time for it is. I don't necessarily think it's 12:30. Sometimes I think it's a children's show. You can run huge portions of my show on Nickelodeon. We have everything but green slime coming down on the guests. So I don't know. I honestly think yes. I've done my share of things in prime time, I've done my share of things earlier in the evening, and you still find the way to do your sense of humor or execute your sensibility in front of a slightly different audience. You're always adjusting to what that specific situation is. If you're hosting the Emmys, you adjust a little. If you're doing a week of shows in a 4,000-seat theatre in Chicago, you make certain adjustments, but still, it's basically you. I have to feel it's the same thing at 11:30. Will the Masturbating Bear still be there? Who can say?
AVC: The best parts of your show tend to be the weird bits.
COB: There's no way my show is going to stop being weird. There will always be an inherent weirdness to anything I'm a part of. Any party I attend, or any family function, I bring a certain weirdness with me that's in my DNA.
AVC: Do you wonder how the archetypal Tonight Show viewer—who's probably a 55-year-old woman in Dubuque, Iowa—will respond to the Walker: Texas Ranger clips, or the screaming raccoon in the jetpack? Are you worried it'll be like The Dana Carvey Show, where you'll be in this very mainstream context, doing this off-the-wall bizarre stuff?
COB: One hope would be that the people who've been watching me for 13 years might come along for that 11:30 ride. It's not like I'm saying goodbye to fans of Late Night. We have a lot of people who have literally grown up with my show. And they tell me it's hard for them to see it now unless they buy TiVo. They started watching it in high school or college, but now they have jobs or a kid, and they aren't up at 12:30. But they have fond memories of the show, and they really want to see it. So I think maybe that's a good time for me to move. There's some hope, clearly, that some of the Conan people will come with me. It won't be a complete introduction to a swath of the country that has me confused with Donny Most from Happy Days.
AVC: Do you see your audience as similar to Jay Leno's?
COB: There's a temptation to overthink the whole thing. I've had a Field Of Dreams philosophy to this: If you build it, they will come. I still have no idea. I don't look at research. I don't look at who's watching, or when they're watching. I've never been interested in any of that. I'm interested in doing what I think is funny. For the last 13 years, that seems to have worked for me. If I go to 11:30 and do what I think is funny, and someone comes and tells me it isn't getting enough people in the tent, I'd say, "Well, that's all I can do." If I'm looking at spreadsheets and time-lapse studies of viewing patterns, I think I'm wasting my time. What I should be worried about the first night I host The Tonight Show is, "How can I make this a funny show?" The second night, "All right, let's make another funny show doing some different stuff." You do it one show at a time. And if you're lucky, eight years later, you've alienated a nation.
AVC: One of your running gags on Late Night has you singing, "I'm going to go to hell when I die!" when you make mean jokes about celebrities.
COB: It wasn't even a running gag. That's just something I spontaneously do at some point. Someone sent me an Internet link. Someone actually put it to music.
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AVC: Is there a part of you that secretly worries that Clay Aiken is in some room sobbing uncontrollably because of all the mean jokes you make about him?
COB: I don't think so. He's getting his reward. I think if Clay Aiken called me up and said, "It really hurts my feelings when you do that, don't do it any more," I'd probably stop. I'm thin-skinned, and as crazy as this sounds, I'm not out to hurt people's feelings. I think I turn the gun on myself a lot. That's part of the world we live in. Who can say? That's between me and my God.
AVC: You're hosting the Emmys again, and it does seem like celebrities at award shows have unusually thin skin. Are you worried that if you go one step too far, they're going to cut to Eva Longoria glaring at you?
COB: I would love it if Eva Longoria glared at me. I'm not that worried about that. I'm going to try and do things that I think might be fun or entertaining. I try to put myself in the audience for these things. I think, "What would be fun to see?" So I don't know. I'm going to try and entertain people. Keeping in mind it's not the television salute to Conan O'Brien, it's the Emmys. It's actually not even about me that much. They need someone to get up there and move it along and get some laughs and try do a little comedy here and there. No, I'm not going to worry too much. It's television. It's not the meeting of the Nobel community. You have to have a sense of humor about it. If someone later on said to me, "The cast of Queer Eye For The Straight Guy is very upset with you," or "Joe Rogan is very hurt," I think I'd live.
It used to be that there was Johnny Carson and there was Bob Hope, and they hosted everything, and no one thought about it. They came out and did their jokes, and they moved it along, and the next day, there weren't articles about how Bob Hope and Johnny did. It changed at some point. And when I hosted the Emmys last time, I remember someone going, "How do you think it's going to go? Are you worried?" People were acting like I was trying to jump Snake River Canyon on a rocket sled.
AVC: It's easy to overanalyze it.
COB: There are 60,000 entertainment publications and websites now. We have a huge, huge volume of opinion to fill. Everyone has got to break down everything. Tale of the tape. I think all you can do is put all that stuff out of your head and try and do something that is funny. And I'll be talking to reporters, and they're like, "How are you going to handle this and that? What's your strategy for getting viewers 18-21 to watch"? You're putting more thought into this than I am. What I do is what you do with your friends. I've somehow scammed my way into getting paid for it. I might think about it a little more, but I'm just someone who is trying to be funny, and sometimes it works great, and sometimes it doesn't, and that's the job. So when you host the awards show, it's the same thing, except you have to be prepared for, "What's your opinion on what he did? What did you think when he turned slightly to the left as opposed to slightly to the right?"
AVC: In a way, you have to be glad that Late Night isn't premièring today, because it seems the scrutiny would be so much more vicious.
COB: I don't know. It was rough in '93, but you're absolutely right. I wake up every morning and think, "I'm so glad I got on the air 13 years ago." It's nice to get to the point where people have pretty much made up their minds, and you do your work and do your thing rather than everyone wildly interpreting what it means. Now I can take a trip to Finland, and people can look at it as a funny thing. I think if I did it in 1993, people would say, "What does it mean, is Conan trying to save his show by going to Finland? Is Conan fleeing to Finland?" You're right. I got in. I'm glad I opened my restaurant 13 years ago.
AVC: That's a crazy thing about television criticism: So much is based around the first episode of any show. But television is a marathon, not a sprint.
COB: Especially these kinds of shows. The point I'm always trying to make is that any TV show that is any good is organic, it's a living thing. If you watch the first Simpsons,it's very different from the 30th Simpsons, or the 80th Simpsons. Dan Castellaneta's voice on the first Simpsons episodes sounded like Walter Matthau. It took a little while for it to come together. This is a show that was pretty much hitting on all cylinders from the beginning, and it nevertheless had to evolve. That's what I think few people understand: A good TV show happens over a period of time. I really like The Office, and I'm not just saying that because I'm friends with [writer-producer] Greg [Daniels]. I really think it's an interesting show, and I think they did a good job with a next-to-impossible task. I've watched that show evolve. They found these different rhythms that they didn't have on the first five or 10 episodes. They found it. You're absolutely right. My show keeps changing. My show is not a finite thing. It's not an iron horseshoe that I can hold up and put on display. It changes from night to night and it's changed over the years. I couldn't have done the Finland thing 5 years in. It would never have happened. If I went to Chicago in 1998 it would not be the same thing as in 2006. When I do The Tonight Show, I'll be a different person, naturally.
AVC: When you delivered your 2000 commencement speech at Harvard, you quoted Tom Shales' review of Late Night, where he said that he hoped you would soon be heading into Conan O'Blivion. And this is the dean of television critics speaking. Did he ever change his tune?
COB: He totally turned around. There's a lot to find fault with [in the early Late Night episodes]. I was green in 1993 and I was replacing Letterman, one of the best people to ever do it. He was at the peak of his skills, and then I jumped in, and the TV critics weren't entirely wrong. If I was a TV critic, I would have found fault with the show. Tom Shales paid attention—he didn't have to do it, but he kept watching the show as it evolved, and it was good enough for him to go back and revise his take.
AVC: The last time you spoke with The A.V Club, you said you never feel like you've really made it. Is that still true now that you're going to host The Tonight Show?
COB: The problem is, you don't. I'm always postponing gratification. If anyone tries to congratulate you, see how you do. See what happens next week. Gee, Jay did it for 20 years, and Johnny did it for 30. If you have this idea in your head that there's a finish line that you can cross, then you'll probably get hit by a bus. But I get gratification for, like, eight minutes, and then I start thinking that what we did is already gone. It's always been my personality. I think the people I really like and admire are probably the same. They're probably always trying to get it right. You never get it quite right. You just don't take it too far, because you'll be miserable. I have the feeling that if I live to be 80 and they throw a banquet celebrating my contributions to television, I'll just be thinking "I've fooled them again!"
Next week at avclub.com: Part two of this interview, in which O'Brien reminisces about his career, including his performance at a 7-year-old's birthday party and a gig at Wilson's House Of Suede And Leather. Oh yeah, and also his work on Saturday Night Live and The Simpsons.