P A R T III

Playboy: You must be getting some good guests. Your ratings have shown a marked improvement.

O'Brien: Remember, when you're on at 12:30 the Nielsens are based on 80 people. My ratings drop if one person has a head cold and goes to bed early.

Playboy: Actually, you're seen by about 3 million people a night. Your ratings would be even higher if college dorms weren't excluded from the Nielsens. How many points does that cost you?

O'Brien: I told you I'm an idiot. Now I have to do math too?

Playboy: Do you still get suggestions from NBC executives?

O'Brien: Not as many. The number of notes you get is inversely proportional to your ratings.

Playboy: What keeps you motivated?

O'Brien: Superstition. We have a stagehand, Bobby Bowman, who holds up the curtain when I run out for the monologue. He is the last person I see before the show starts, and I have to make him laugh before I go out.

� � �It started with mild jabs: "Bobby, you're drunk again." Bobby laughs, heehee. Then it was, "Still having trouble with the wife, Bobby?" But after hundreds of shows, you find yourself running out of lines. It's gotten to where I do crass things at the last second. I'll put his hand on my ass and yell, "You fucking pervert!" Or drop to my knees and say, "Come on, Bobby, I'll give you a blow job!"

� � �"Ha-ha. Conan, you're crazy," he says. But even that stuff wears off. Soon, I'll be making the writers work late to give me new jokes for Bobby.

Playboy: Did you plan to be a talk show host or did you fall into the job?

O'Brien: I was an Irish Catholic kid from St. Ignatius parish in Brookline, outside of Boston. And that meant: Don't call attention to yourself. Don't ask for too much when the pie comes around. Don't get a girl pregnant and fuck up your life.

Playboy: Were you an alter boy?

O'Brien: I wanted to be an alter boy, but the priest at St. Ignatius said, "No, no. You're good on your feet, kid," and made me a lector. A scripture reader at Mass. He was the one who spotted my talent.

Playboy: What did you think of sex in those days?

O'Brien: I was sexually repressed. At 16 I still thought human reproduction was by mitosis.

Playboy: How did you get over your sexual repression?

O'Brien: Who says I got over it? My leg has been jiggling this whole time.

Playboy: What were you like in high school?

O'Brien: Like a crane galumphing down the hall. A crane with weird hair, bad skin and Clearasil. Big enough for basketball but lousy at it. My older brothers were better. I would compensate by running around the court doing comedy, saying, "Look out, this player has a drug addiction. He's incredibly egotistical."

� � �I was an asshole at home, too. My little brother Justin loved playing cops and robbers, but I kept tying him up with bureaucratic bullshit. When he'd catch me, I'd say, "I get to call my lawyer." Then it was, "OK, Justin, we're at trial and you've been charged with illegal arrest. Fill out these forms in triplicate." Justin was eight; he hated all the lawsuits and countersuits. He just cried.

Playboy: Were you a class clown?

O'Brien: Never. I was never someone who walked into a room full of strangers and started telling jokes. You had to get to know me before I could make you laugh. The same thing happened with Late Night. I needed to get the right rhythm with Andy and Max and the audience.

Playboy: So how did you finally learn about sex?

O'Brien: My parents gave me a book, but it was useless. At the crucial moment, all it showed was a man and a woman with the bed covers pulled up to their chins. I tried to find out more from friends, but it didn't help. One childhood friend told me it was like parking a car in a garage. I kept worrying about poisonous fumes. What if the fumes build up? Should you shut off the engine?

Playboy: For all your talk about being repressed, you can be rowdy on the air.

O'Brien: The show is my escape valve. When I tear off my shirt and gyrate my pelvis like Robert Plant, feigning orgasm into the microphone, that shows how repressed I am -- a guy who wants to push his sex at the lens but can only do it as a joke.

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 the 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 the 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 approachable amount of beauty becomes almost funny. It's the same with male supermodels. 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 the 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 John.

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. Sometimes 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's 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 look funny.

Playboy: Johnny Carson never licked Ed McMahon.

O'Brien: We are much more physical and more 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'm blessed not to be a 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 Grammar 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 Grammar 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 after 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 "Whoo!" 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 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 clothing, 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 sphinter costume and a cowboy hat. He says, "Hi kids, I'm Randy the Pyloric Sphinter. 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 spincter 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. "Here's the sketch: Conan jumps into a barrel of wheat germ." I'll ask him what 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 paycheck.

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.

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