PLAYBOY Interview With Conan O'Brien
Interview by Kevin Cook For Playboy Magazine February 1998
Part 2
Playboy: Really? You have never admitted that.
O'Brien: This is the first time I've talked about it. When I had been on for about a year, there was a meeting at the network. They decided to cancel my show. They said, "It's cancelled." Next day they realized they had nothing to put in the 12:30 slot, so we got a reprieve.
Playboy: Were you worried sick?
O'Brien: I went into denial. I tried hard not to think, Yes, I'm bad on the air and my show has none of the things a TV show needs to survive. We had no ratings. No critics in our corner. Advertisers didn't like us. Affiliates wanted to drop us. Sometimes I'd meet a programming director from a local station where we had no rating at all. The guy would show me a printout with no number for Late Night's rating, just a hash mark or pound sign. I didn't dare think about that when I went out to do the show.
Playboy: Are you defending denial?
O'Brien: How else does anyone get through a terrible experience? The odds were against me. Rationally, I didn't have much chance. Denial was my only friend. When I look back on the first year, it's like a scene from an old war movie: Ordinary guy gets thrown into combat, somehow beats impossible odds, staggers to safety. His buddy say, "You could have been killed!" The guy stops and thinks. "Could have been killed?" he says. His eyes cross and he faints.
Playboy: How did you dodge the bullet?
O'Brien: There were people at NBC who stood up for me. I will always be indebted to Don Ohlmeyer, who stuck to his guns. Don said, "We chose this guy. We should stick with him unless we get a better plan." He was brutally honest. He came to me and said, "Give me about a 15 percent bump in the ratings and you'll stay on the air. If not, we're going to move on."
Playboy: Ohlmeyer started his career in the sports division.
O'Brien: Exactly, his take was, "You're on our team." Of course, it wasn't exactly rational of Don to hope I'd be 15 percent funnier. It was like telling a farmer, "It better rain this week or we'll take your farm away."
Playboy: What did you say to Ohlmeyer?
O'Brien: There wasn't time. I had to go out and do a monologue. But I will always be indebted to Don because he told me the truth. Wait a minute -- you have tricked me into talking lovingly about an NBC executive. Let me say that there were others who were beneath contempt -- executives who wouldn't know a good show if it swam up their asses and lit a campfire.
Playboy: Finally the ratings went your way. Hard work rewarded?
O'Brien: Well, I also paid off the Nielsen people. That was $140,000 well spent.
Playboy: Ohlmeyer plus bribery saved you?
O'Brien: There was something else. Just when everyone was kicking the crap out of the show, Letterman defended me.
Playboy: Letterman had signed off on NBC saying, "I don't really know Conan O'Brien, but I heard he killed someone."
O'Brien: Then I pick up the paper and he's saying he thinks I am going to make it. "They do some interesting, innovative stuff over there," he says. "I think Conan will prevail." And then he came on as a guest. Remember, this was when we were at our nadir. There was no Machiavellian reason for David Letterman, who at the time was the biggest thing in show business, to be on my show.
Playboy: Why did he do it?
O'Brien: I'm still not sure. Maybe out of a sense of honor. Fair play. And it woke me up. It made me think. Hey, we have a real fucking television show here.
Of six or seven pivotal points in my short history here, that was the first and maybe the biggest. I wouldn't be sitting here -- I probably wouldn't even exist today -- if he hadn't done our show.
Playboy: The Late Night wars were hardly noted for friendly gestures.
O'Brien: How little you understand. Jay, Dave and I pal around all the time. We often ride a bicycle built for three up to the country. "Nice job with Fran Drescher!" "Thanks, pal. You weren't so bad with John Tesh." We sleep in triple-decker bunk beds and snore in unison like the Three Stooges.
Playboy: You talk more about Letterman than your NBC teammate Leno.
O'Brien: I hate the "Leno or Letterman, who's better?" question. I can tell you that Jay has been great to me. He calls me occasionally.
Playboy: To say what?
O'Brien: (Doing Leno's voice) "Hey, liked that bit you did last night." Or he'll say he saw we got a good rating. I call him at work, too. It can be a strange conversation because we're so different. Jay, for instance, really loves cars. He's got antique cars with kerosene lanterns, cars that run on peat moss. He'll be telling me about some classic car he has, made entirely of brass and leather, and I'll say, "Yeah, man, I got the Taurus with the vinyl." One thing we have in common is bad guests. There are certain actors, celebrities with nothing to say, who move through the talk show world wreaking havoc. They lay waste to Dave's town and Jay's town, then head my way.
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.
Copyright Playboy Magazine 1998