Playboy: Aren't you tempted to live it up?
O'Brien: I always imagined that if I were a TV star I would live the way I pictured Johnny Carson living. Carousing, stepping out of a limo wearing a velvet ascot with a model on my arm. Now that I have the TV show, I drive up to Connecticut on weekends and tool around in my car. I could probably join a free-sex cult, smoke crack between orgies and drive sports cars into swimming pools, and my Catholic guilt would still be there, throbbing like a toothache. Be careful. If something good happens, something bad is on the way.
Playboy: Yet you don't mind licking supermodels.
O'Brien: At one point a few of them lived in my building, women who are so beautiful they almost look weird, like aliens. To me, a woman who has a certain unapproachable amount of beauty becomes almost funny. It's the same with male models. They look like big puppets. So while I admire their beauty I probably won't be "romantically linked" with a model. I'd catch my reflection in a ballroom mirror and break up laughing.
Playboy: The horny Roy Orbison growl you use on gorgeous guests sounds real enough ----
O'Brien: Oh, I've been doing that shit since high school. It just never worked before.
Playboy: Your father is a doctor, your mother an attorney. What do they think of their son the comedian?
O'Brien: My dad was the one who told me denial was a virtue. "Denial is how people get through horrible things," he said. He also cut out a newspaper article in which I said I was making money off something for which I should probably be treated. So true, he thought. But when I got an Emmy for helping write Saturday Night Live, my parents put it on the mantel next to a crucifix. Here's Jesus looking over, saying, "Wow, I saved mankind from sin, but I wish I had an Emmy."
Playboy: Ever been in therapy?
O'Brien: Yes. I don't trust it. I have told therapists that I don't particularly want to feel good. "Repression and fear, that's my fuel." But the therapists said that I had nothing to worry about. "Don't worry, Conan, you will always be plenty fucked up."
Playboy: When a female guest comes out, how do you know whether to shake her hand or kiss her? Is that rehearsed?
O'Brien: No, and it's awkward. If you go to shake her hand and her head starts coming right at you, you have to change strategy fast. I have thought about using the show to make women kiss me, but that would probably creep out the people at home. I decided not to kiss Elton.
Playboy: Do you get all fired up if Cindy Crawford or Rebecca Romijn does the show?
O'Brien: I like making women laugh. Always have, ever since I discovered you can get girls' attention by acting like an ass. That's one of the joys of the show -- I'm working my eyebrows and going grrr and she's laughing, the audience is laughing. It's all a big put-on and I'm thinking, This is great. Here is a beautiful woman who has no choice but to put up with this shit. But it's not always put on. Sometimes they flirt back. Occasionally there's a bit of chemistry. That happened with Jennifer Connelly of The Rocketeer.
Playboy: One guest, Jill Hennessy, took off her pants for you. Then you removed yours. Even Penn and Teller took off their pants.
O'Brien: Something comes over me. It happened with Rebecca Romijn -- I was practically climbing her. Those are the times when Andy and the audience seem to disappear and it's just me and this lovely woman sitting there flirting. I keep expecting a waiter to say, "More wine, Monsieur?"
Playboy: Would you lick the wine bottle?
O'Brien: It's true, there is a lot of licking on the show. I have licked guests. I have licked Andy. Comedy professionals will read this and say, "Great work, Conan. Impressive." But I have learned that if you lick a guest, people laugh. If I pick this shoe off the floor, examine it, Hmmm, and then lick it, people laugh. I learned this lesson on The Simpsons, where I was the writer who was forever trying to entertain the other writers. I still try desperately to make our writers laugh, which is probably a sign of sickness since they work for me now. Licking is one of those things that looks funny.
Playboy: Johnny Carson never licked Ed McMahon.
O'Brien: We are much more physical and stupid than the old Tonight Show. Even in our offices before the show there's always some writer acting out a scene, crashing his head through my door. A behind-the-scenes look at our show might frighten people.
Playboy: One night you showed a doctored photo of Craig T. Nelson having sex with Jerry Van Dyke. Did they complain about it?
O'Brien: I haven't heard from them. Of course I am blessed not to be part of the celebrity pond. I have a television show in New York, an NBC outpost. I don't run with or even run into many Hollywood people.
Playboy: You also announced that Tori Spelling has a penis.
O'Brien: I did not. Polly the Peacock said that.
Playboy: Another character you use to say the outrageous stuff.
O'Brien: Polly is not popular with the network.
Playboy: You mock Fabio, too.
O'Brien: If he sues me, it'll be the best thing that ever happened. A publicity bonanza. Courtroom sketches of Fabio with his man-boobs quivering, shaking his fist, and me shouting at him across the courtroom. I'm not afraid of Fabio. He knows where to find me. I'm saying it right here for the record: Fabio, let's get it on.
Playboy: Ever have a run-in with an angry celeb?
O'Brien: I did a Kelsey Grammer joke a few years ago, something about his interesting lifestyle, then heard through the network that he was upset. He had appeared on my show and expected some support. At this point my intellect says, "Kelsey Grammer is a public figure. I was in the right." Then I saw him in an airport. Kelsey didn't see me at first; I could have kept walking. But there he was, eating a cruller in the airport lounge. I thought I should go over. I said hello and then said, "Kelsey, I'm sorry if I upset you." And he was glad. He looked relieved. He said, "Oh, that's OK." We both felt better.
Playboy: Now that you're doing so well, do you worry about losing your edge?
O'Brien: I fear being a victim of success. It's seductive. You have new choices. "Conan, Sylvester Stallone wants to be on, but we're already booked." My feeling is that I must say no to Stallone. "Sorry, Sly. Bob Denver's on that night."
Playboy: How's your relationship with NBC executives now that the show is a success?
O'Brien: Better. But I have not forgotten the bad old days. Let me tell you about one executive. He's no longer with the company. I had him killed. But in our darker days he came to the set one night when we did a great show. I come off after the show and this guy says, "Wow, that was terrible." He thought the show should look like MTV. "Run into the audience and tell jokes. Run up to a guy, have him shout his name, get everybody cheering."
Playboy: You didn't agree, apparently.
O'Brien: Too much of television is energy with no purpose. People going "Whooo!" But that's just empty energy. That's American Gladiators. I often try to lower the energy, especially when school is out and college kids are here. They're huge fans, they're psyched, but we're a quirky weird comedy show, not MTV Spring Break.
Playboy: Were you thrilled when the Marv Albert sex case hit the news?
O'Brien: Oh man, was I into Marv. I would love to trick you into thinking I'm high-minded, but that story made me think, My God, yes, I'll use this, and this . . . But it bothered me the way he was publicly vilified. People were getting off on the kinky stuff; they condemned Marv for wearing women's clothes, which isn't a crime.
Playboy: Yet tonight you did a Marv Albert joke. You said Marv had a new job as a mannequin at Victoria's Secret.
O'Brien: You can be uncomfortable with it and still use it. Isn't that what guilt is all about?
Playboy: What comedy bits do you regret doing?
O'Brien: We did one with a character called Randy the Pyloric Sphincter. Now, the point of the joke is that this is not the sphincter that excrement passes through. The pyloric sphincter is at the top of the digestive tract. It basically keeps acid from going up into the esophagus. We had a guy in a sphincter costume and a cowboy hat. He says, "Hi kids, I'm Randy the Pyloric Sphincter. No, not that bad sphincter! When food passes through me, it isn't digested yet." He then proceeds to squeeze foods that look like shit whether they're digested or not. Chocolate. Picture a sphincter exuding a huge chocolate bar. We were grossing people out.
Playboy: So why put Randy on the air?
O'Brien: I just loved the fact that he wore a cowboy hat.
Playboy: What sorts of bits do you refuse to do?
O'Brien: Arbitrary humor. A writer says, "Here's the sketch: Conan jumps into a barrel of wheat germ." I'll ask him where the joke is. "It's crazy, that's all." Look, I was a comedy writer. I've been through this before. If the joke is that there is no joke, the writer gets no check.
Playboy: Jumping into wheat germ sounds like Letterman.
O'Brien: My show began with me and everyone involved with the show doing all we could to avoid being anything like Letterman. Which is difficult. He invented a lot of the form. He carved out a big territory. He's the Viking who discovered America, and now I have my little piece of northwestern Canada that I'm trying to claim as my own.
Playboy: So how do you avoid being Dave-like?
O'Brien: We have always scrupulously avoided found comedy. You never see me going up and talking to normal Joe on the street. The real world of people, dogs, cabbies -- Letterman is great at that. His genius, I think, is playing with the real world around him. Which is not my forte at all. My idea is more about creating a fake, cartoony world and playing with that.
Playboy: Are you goofy in real life?
O'Brien: My private life is boring. I have been with the same woman, Lynn Kaplan, for four years, and there ain't nothing crazy going on. Lynn is a talent booker on our show. We go to my house in Connecticut on weekends. I sit around playing guitar.
Playboy: Gossip columns have placed you in Manhattan with other women.
O'Brien: One of them had me with Courteney Cox. Lisa Kudrow and I did improv together years ago and we went out for a while. Maybe that's why I can now be romantically linked to the entire cast of Friends. I may be thrilled with that, but my girlfriend is one of those people who believe everything they read in the tabloids. She's sitting at the table in Connecticut when she opens a tabloid and says, "What the hell?" There's a big photo of me with Courteney Cox. The story says, "Courteney's moving in with Conan."
Playboy: Did Lynn believe it?
O'Brien: No, because the story went on to say, "Conan and Courteney were seen at the Fashion Cafe munching veggie burgers." That sentence ended her faith in tabloids. Lynn knows that I would never (a) go to the Fashion Cafe and (b) eat a veggie burger. I'm an Irish Catholic kid from Boston; I'll eat red meat until my heart explodes out of my chest.
Playboy: Do you still drive an old Ford Taurus?
O'Brien: When I got my five-year contract I moved up. Bought a Range Rover. Now I drive the Range Rover to Connecticut for the weekend, park it and tool around in the Taurus all weekend. I can't let go of that Taurus. It's an extension of my penis.
Playboy: Can you forget about the show all weekend?
O'Brien: I drive around playing Jerry Reed tapes, fantasizing that I'm some backwoods character. But even then -- you know, it's probably not an accident that people who do these shows tend to be depressive. You want so badly for it to be right every night, but mounting an hour-long show four times a week -- the pace will kill you. One night I put my fist through a tile wall. Another night I walked off the stage, pulled an air-conditioning unit out of the wall and kicked it. This is stuff I can't explain. Nor can I excuse it. But there may be something maddening about these shows. The pace is . . . I forget shows we did last week. That's why I can't imagine doing this for 30 years. I bet you could show Johnny Carson footage of how he shrieked as his body was lowered into acid and he'd say, "Hmm, don't remember that one." I saw Jerry Seinfeld at the Emmy Awards. He said he liked the show, then he paused and said, "How do you do it?" "Do what?" "Do what you do every night for an hour?" That shocked me. This is Jerry Seinfeld, the master. A man everyone can agree is funny. And I really have no answer.