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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