Playboy Interview: Conan O'Brien

By Kevin Cook

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Playboy Interview: Conan O'Brien:

He was polite. He was funny. He gave us a communicable disease.

At 34, Conan O'Brien is hotter than the fever he was running when we met in his private domain above the Late Night soundstage. A gangly, freckle-faced ex-high school geek, he is “one of TV’s hottest properties,” according to People magazine. The host of Late Night With Conan O'Brien has become his generation’s king of comedy.

Uneasy lies the head that wears a crown. Congested, too, but O'Brien has far more to worry about than this head cold. A perfectionist who broods over one bad minute in an otherwise perfect hour of TV, he worries he might be anhedonic. “I have trouble with success,” he says. “I was raised to believe that if something good happens, something bad is coming.” Sure, things look good now. Rolling Stone calls Late Night “the hottest comedy show on TV.” Ratings are better than ever, particularly among 18- to 34-year-olds, the viewers advertisers crave.

But O'Brien only works harder. Despite his illness, he taped two shows in 26 hours on three hours' sleep. He smoothly interviewed Elton John, then burst into coughing fits during commercials. Later, in his cramped corner office overlooking Manhattan traffic, Conan the Cool gulped DayQuil gel caps. He coughed, spewing microbes.

“Sorry, sorry,” he said. Of course, O'Brien can’t complain. He came seriously close to failing, to being banished behind the scenes as just another failed talk show host.

At his first Late Night press conference he corrected a reporter who called him a relative unknown. “Sir, I am a complete unknown,” he said. That line got a laugh, but soon O'Brien look doomed. His September 13, 1993 debut began with O'Brien in his dressing room preparing to hang himself, only to be interrupted by the start of the show. Before long his career was hanging by a thread. Ratings were terrible. Critics hated the show. Tom Shales of The Washington Post called it as “lifeless and messy as roadkill.” Shales said O'Brien should quit.

Network officials held urgent meetings, discussing the Conan O'Brien debacle. Should they fire him? How should they explain their mistake?

In the end, of course, he turned it around. The network hung with him long enough for the ratings to improve, and the host of the cooler-than-ever Late Night now defines comedy’s cutting edge, just as Letterman did ten years ago.

Even Shales loves Late Night these days. He calls O'Brien’s turnaround “one of the most amazing transformations in television history.”

O'Brien was born on April 18, 1963 in Brookline, Massachusetts. His father, a doctor, is a professor at Harvard Medical School. His mother, a lawyer, is a partner at an elite Boston law firm. Conan, the third of six O'Brien children, became a lector at church and a misfit at school. Tall and goofy, bedeviled with acne, he tried to impress girls with jokes. That plan usually bombed, but O'Brien eventually found his niche at Harvard, where he won the presidency of the Harvard Lampoon in 1983 and again in 1984 – the first two-time Lampoon president since humorist Robert Benchley held the honor 85 years ago.

After graduating magna cum laude with a double major in literature and American history, he turned pro. Writing for HBO’s Not Necessarily the News, O'Brien was earning $100,000 a year before his 24th birthday. But writing was never enough.

He honed his performance skills with the Groundlings, a Los Angeles improv group. There he worked with his onetime girlfriend Lisa Kudrow, now starring on Friends. But Conan was not such a standout. In 1988 he landed a job at Saturday Night Live – but as a writer, not as on-air talent. In almost four years on the show O'Brien made only fleeting appearances, usually as a crowd member or security guard. His writing was more memorable. He wrote (or co-wrote) Tom Hanks' Mr. Short-Term Memory skits as well as the “pump you up” infosatire of Hanz and Franz and the nude beach sketch in which Matthew Broderick and SNL members played nudists admiring one another’s penises. With dozens of mentions of the word, that bit was the most penis-heavy moment in TV history. It helped O'Brien win an Emmy for comedy writing.

In 1991 he quit SNL and moved on to The Simpsons, where he worked for two years. His urge to perform came out in wall-bouncing antics in writers' meetings. “Conan makes you fall out of your chair,” said Simpsons creator Matt Groening. O'Brien’s yen to act out was so strong that he spurned Fox’s reported seven-figure offer to continue as a writer. He was dying for the spotlight.

By then David Letterman had announced he was jumping ship – leaving NBC, taking his top-rated act to CBS. Suddenly NBC was up a creek without a host. The network turned to Lorne Michaels, O'Brien’s Saturday Night Live boss. Michaels enlisted Conan’s help in the host search, planning to use him in a behind-the-scenes job. But when Garry Shandling, Dana Carvey and almost every other star turned down the chore of following Letterman, Michaels finally listened to Conan’s crazy suggestion: “Let me do it.” Michaels persuaded the network to entrust its 12:30 slot, which Letterman had turned into a gold mine, to an untested wiseass from Harvard.

O'Brien was working on one of his last Simpsons episodes when he got the news. He turned “paler than usual,” Groening recalled. Then Conan moseyed back to where the other writers were working. “I’ll come back with the Homer Simpson joke later. I have to go replace Letterman,” he said.

NBC executives now get credit for their foresight during those dark days of 1993 and 1994. They spared the ax and now reap the multimillion-dollar spoils of that decision. In fact, the story is not so simple. We sent Contributing Editor Kevin Cook to unravel the tale of O'Brien’s survival, which he tells here for the first time. Cook reports:

“His office is chock-full of significa. There’s a three-foot plastic pickle the Letterman staff left behind in 1993 – perhaps to suggest what a predicament he was in. There’s a copy of Jack Paar’s ‘I Kid You Not’ and a coffee-table book called Saturday Night Live: The First 20 Years. His bulletin board features letters from fans such as John Waters and Bob Dole, and an 8"x10” glossy of Andy Richter with the inscription: ‘To Conan – Your bitter jealousy warms my black heart. Love and Kisses, Andy.’

“Of course it’s all for show. From the photos of kitsch icons Adam West and Robert Stack to the framed Stan Laurel autograph, from the deathbed painting of Abraham Lincoln to the ironic star taped to Conan’s office door – they’re all clever signals that tell a visitor how to view the star. Lincoln was his collegiate preoccupation; stardom is his occupation. Somewhere between the two I hoped to find the real O'Brien.

"As a Playboy reader, he wanted to give me a better-than-average interview. I wanted something more – a definitive look at the guy who may end up being the Johnny Carson of his generation.

Playboy: Here’s hoping we succeeded. If not, I carried his germs 3000 miles and infected dozens of Californians for no good reason.

O'Brien: Yes, this is how to do the Playboy Interview – completely tanked on cold medicine. I’ll pick it up and read, "Yes, I’m gay.”

Playboy: We could talk another time.

O'Brien: [Coughing] No, it’s OK. I memorized Dennis Rodman’s answers. Can I use them?

Playboy: You sound really sick. Do you ever take a day off?

O'Brien: No. The age of talk show hosts' taking days off is over. Johnny Carson could go to Africa when he was the only game in town – “See you in two weeks!” But nobody does that now. I will give you a million dollars on the first day Jay takes off for illness.

Playboy: Do you ever slow down and enjoy your success?

O'Brien: If anything, the pace is picking up. Restaurateurs insist on giving me a table even if I’m only passing by, so I’m eating nine meals a night. Women stop me on the street and hand me their phone numbers.

Playboy: So you have groupies?

O'Brien: Oh yes. And other fans. Drifters. Prisoners. Insomniacs. Cab drivers, who must watch a lot of late-night TV, seem to love me lately. They keep saying, “You will not pay, you will not pay, you make me happy!”

Playboy: How happy did your new contract make you?

O'Brien: Terrified. The network said, “We’re all set for five years.” I said, “Shut up, shut up! I can’t think that far ahead.” Tonight, for instance, I do my jokes, then interview Elton John and Tim Meadows. We finished taping about 6:30. By 6:45 my memory was erased and my only thought was, Tomorrow: John Tesh. And I started to obsess about John Tesh. Sad, don’t you think?

Playboy: Not too sad. You got off to a rocky start, but now you’re so hot that People magazine recently said, “That was then, this is wow.”

O'Brien: I try not to pay much attention. Since I ignored the critics who said I should shoot myself in the head with a German Luger, it would be cheating to tear out nice reviews now and rub them over my body, giggling. Though I have thought about it.

Playboy: Tell us about your trademark gag. You interview a photo of Bill Clinton or some other celeb, and a pair of superimposed lips provides outrageous answers.

O'Brien: We call it the Clutch Cargo bit, after that terrible old cartoon series. They saved money on animation by superimposing real lips on the cartoons. I wanted to do topical jokes in a cartoony way – not just Conan doing quips at a desk. TV is visual; I want things to look funny. But we’re not Saturday Night Live; we couldn’t spend $100,000 on it. Hence the cheap, cheesy lips. You’d be surprised how many people we fool.

Playboy: Viewers believe that’s really the president yelling, “Yee-ha! Who’s got a joint?”

O'Brien: It’s strange. You may know intellectually that Clinton doesn’t talk like Foghorn Leghorn. Ninety-eight percent of your brain knows the president wouldn’t say, “Whoa, Conan, get a load of that girl!” But there are a few brain cells that aren’t sure. When Bob Dole was running for president we had him doing a past-life regression: “My cave, get away.” And then back further: “Must form flippers to climb onto rocky soil,” he says. There may be people out there who believe that Bob Dole was the first amphibian.

Playboy: Do you ever go too far?

O'Brien: The fun is in going too far. It’s a nice device because you get Bill Clinton to do the nastiest Bill Clinton jokes. We’ll have Clinton make fart noises while I say, “Sir! Please!”

Playboy: Are you enjoying your job now, with your new success?

O'Brien: Well, there are surprises. I hate surprises. Like most comedians, I’m a control freak. But I’m learning that the show works best when it’s out of control. Tonight I ask Elton John if he likes being neighbors with Joan Collins. He says he isn’t neighbors with Joan Collins. He lives next door to Tina Turner. So I panic – huge mistake! But Elton saves the day. “Joan Collins, Tina Turner, it doesn’t matter. Either way I could borrow a wig,” he says. Huge laugh, all because I fucked up. Later he surprised me by blurting out that he’s hung like a horse. The camera cuts to me shaking my head: That crazy Elton. What can I do? Of course I’m delighted that he went too far.

Playboy: That “What can I do?” look resembles a classic take of Jack Benny’s.

O'Brien: There’s an old saying in literature: “Good poets borrow, great poets steal.” I think T.S. Eliot stole it from Ezra Pound. Comics steal, too. Constantly. When I watched Johnny Carson I noticed that he got a few takes from Benny and Bob Hope. When a comedy writer told me how much Woody Allen had borrowed from Hope, I thought, What? They’re nothing alike. Then I went back and watched “Son of Paleface,” and there’s Hope the nervous city guy backing up on his heels, wringing his hands and saying, “Sorry, I’ll just be moving along.” Now look at early Woody Allen. You see big authority figures and Woody nervously saying, “Look, I’ll just be on my way.” Of course Woody made it his own, but he must have watched and loved Bob Hope.

Playboy: Who are your role models?

O'Brien: Carson. Woody Allen. SCTV. Peter Sellers. When Peter Sellers died I felt such a loss, thinking, There won’t be any more of that. There’s some Steve Martin in my false bravado with female guests: “Why, hel-lo there!” And I won’t deny having some Letterman in my bones.

Playboy: You were a surprise as Letterman’s successor. At first you seemed like the wrong choice.

O'Brien: I didn’t get ratings. That doesn’t mean I didn’t get laughs. Yes, I had a giant pompadour and looked like a rockabilly freak. I was too excited, pushed too hard, and people said, “That guy isn’t a polished performer.” Fine! But it isn’t my goal to be Joe Handsomehead, cool, smooth talk show host. Late Night With Conan is supposed to be a work in progress, and now that we’ve had some success there’s a danger of our getting too polished and morphing into something smoothly professional. Which would suck. Do you know why I wanted this show? Because Late Night With David Letterman played with the rules and it looked like fun. Here was a place where people did risky comedy every night for millions of people. We had to keep this thing alive. There should be a place on a big network where people are still messing around.

Playboy: How bad were your early days on the show?

O'Brien: Bad. Dave left here under a cloud; his fans and the media were angry with NBC. Then NBC picks a guy with crazy hair and a weird name. From Harvard. And the world says, “Harvard? Those guys are assholes.” I sincerely hope that the winter of December 1993, our first winter, was the worst time I will ever have. I’d go out to do the warm-up and the back two rows of seats would be empty. That’s hard to look at. I would tell a joke and then hear someone whisper, “Who’s he? Where’s Dave?”

Playboy: You had trouble getting guests.

O'Brien: Bob Denver canceled on us. We shot a test show featuring Al Lewis of The Munsters. We did the Clutch Cargo thing with a photo of Herman Munster. Unfortunately Fred Gwynne, who played Herman, had recently died, and Al Lewis kept pointing at the screen, saying, “You’re dead! I was at your funeral!”

Playboy: For months you got worried notes from network executives. What did they say?

O'Brien: They were worried. The fact that Lorne Michaels was involved bought me some time. But Lorne had turned to me at the start and said, “OK, Conan. What do you want to do?” Now television critics were after me and the network was starting to realize what a risk I was. Suggestions came fast and furious. I kept the note that said, “Why don’t you die?”

Playboy: Did they suggest ways to be funnier?

O'Brien: They were more specific and tactical. The network gets very specific data. Say there was a drop in the ratings between 12:44 and 12:48 when I was talking to Jon Bon Jovi. I’ll be told, “Don’t ever talk to him again.” Or they’ll want me to tease viewers into staying with us: “You should tease that – say, ‘We’ll have nudity coming up next!’”

Playboy: You did come close to being canceled.

O'Brien: We were canceled.

Playboy: Really? You have never admitted that.

O'Brien: This is the first time I’ve talked about it. When I had been on about a year, there was a meeting at the network. They decided to cancel my show. They said, “It’s canceled.” Next day they realized they had nothing else 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 says, “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 [NBC West Coast president] 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.”

Playboy: What did you say to Ohlmeyer?

O'Brien: There wasn’t time. I had to go out and do a monolog. But I will always be indebted to Don because he told me the truth. Wait a minute – you have somehow 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 hear he killed someone.”

O'Brien: Then I pick up the paper and he’s saying he thinks I’m going to make it. “They do some interesting, innovative stuff over there,” he says. “I think Conan will prevail.” And then he came on my show 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 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 about 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 costs 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 monolog. 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, hee-hee. 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 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 altar boy?

O'Brien: I wanted to be an altar 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 time 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 bedcovers 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 fumes build up? Should you shut off the engine?

Playboy: For all your talk of 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 an 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 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.

Playboy: Praise from Seinfeld must cheer you up.

O'Brien: [Shaking his head] I worry that we have hit our stride and must be headed for a fall. Because every show has an arc. The Honeymooners had an arc. People forget, but at the beginning The Honeymooners was mean and depressing. Art Carney wasn’t fun and cuddly yet. Even successful shows take time to find their rhythm. Then they get self-indulgent and fuck it up. Look at late Happy Days episodes. They quit shooting on location, Mork keeps visiting, and it’s an excuse to spin off new shows.

Playboy: Will you fuck it up, too?

O'Brien: Eventually my only consolation may be that I get paid a lot. I’ll say, “I know it sucks, but I’m getting $65 million a year!”

Playboy: Letterman said almost exactly that not long ago. When a joke died he admitted it sucked. “But I’m making a fortune!” he said. Do you really worry about losing your edge?

O'Brien: I want a living will for my career. I want the people around me to pull the plug when I become a self-parody, an old blowhard like Alan Brady. Remember him, the television star Rob Petrie worked for on the Dick Van Dyke Show? Pompous, over-the-top, over-the-hill. I don’t want to be Alan Brady.

Playboy: Letterman paid you an odd compliment. “When I see that show it withers me with exhaustion,” he said.

O'Brien: That’s our new slogan. “Watch Late Night – We’ll Wither You.” But I think Dave was saying that he knows how hard it is to make a show like this every night.

Playboy: Suppose Leno left The Tonight Show. Would you like to duel Dave at 11:30?

O'Brien: Our best slot would be eight a.m. We have puppets, cartoons, lots of childishness. I think I’m doing an OK late-night show but a great kids' show.

Playboy: This from Mr. Hip?

O'Brien: No. When someone says this or that sort of comedy is hip and alternative – “Yes, these are the cool people” – I hate that. Because at the end of the day, funny is funny. People get fooled about me because I went to Harvard. “He’s cerebral.” But I love Green Acres. I love how Green Acres bends reality.

Playboy: Sounds cerebral.

O'Brien: It isn’t. In one episode Oliver Douglas has to go to Washington, D.C. His wife says, “Darling, take a picture of the Eiffel Tower.” He says, “Lisa, the Eiffel Tower —- ” Then Eb comes in. “Mr. Douglas, git me an Eiffel Tower postcard!” Now Oliver is terribly frustrated. He keeps sputtering about Washington, D.C., but nobody listens. At the end, he goes to Washington, looks up and there’s the Eiffel Tower. That is the kind of thing that made me love TV.

Playboy: As a TV-mad college kid you cooked up scams to meet celebs.

O'Brien: I wanted to meet Bill Cosby, so my friends and I offered him some fake award. We took a bowling trophy and called it the Harvard Comedy Award, something like that, and Cosby, thinking it was the Hasty Pudding Award, accepted. So I drive out to meet his private plane. “Over here, Mr. Cosby!” And I chauffeur him in my dad’s secondhand station wagon. Cosby sits in the backseat, picking old McDonald’s wrappers off the floor, and says, “This is about the Hasty Pudding Award?” “Oh no, nothing like that.”

Playboy: You tricked Bill Cosby into letting you drive him around?

O'Brien: I didn’t realize that one does not pick up a famous person in a 1976 station wagon. They like to fly first-class, to be picked up in a Town Car and put up in a nice hotel. Fortunately I am not directly involved in celebrity care anymore.

Playboy: Did you bring other comics to Harvard?

O'Brien: Yes. John Candy’s people warned me that John was on the Pritikin diet. They gave me strict dietary instructions. John immediately ran into a bakery on Harvard Square to get pastries. He said they were Pritikin eclairs.

Playboy: You once stole a famous television costume.

O'Brien: When Burt Ward visited Harvard there were fliers all over campus: Burt Ward to Appear With Original Robin Costume (Insured by Lloyd’s of London for $500,000). In fact, Burt Ward was said to keep a bunch of them in his car; he’d pass them out to impress girls. Naturally, I wanted to screw with him. A few friends and I attended his speech at the science center. We went dressed as security guards. I said, “Mr. Ward, I’ve been sent by the dean to safeguard the costume.” As if it were the Shroud of Turin. But the guy is humorless. “Yes, very good. That costume is very valuable,” he says. That’s when we hit the lights. Which works great in the movies. In the movies, the lights go out and suddenly the jewel is gone. In real life, though, what you get is some dimming. You hit the lights and people can see a little less well.

Playboy: Did you grab the costume?

O'Brien: We grabbed it and the chase was on. Some Burt Ward admirers – young Republicans, I guess – took off after us yelling, “Stop them!” But we escaped in a waiting car. We proceeded to torment Burt Ward for hours on the phone, saying, “This is the Joker, hee-hee-hee. I’ve got your costume.”

Playboy: How did Burt react?

O'Brien: Robinlike. He said, “Return it or you will feel my wrath!”

Playboy: Burt Ward used to tell reporters he had an IQ of 200.

O'Brien: He may be delusional.

Playboy: Were you always starstruck?

O'Brien: Stars are fascinating. When I was a writer for Saturday Night Live, Robert Wagner did the show. One day he was sitting offstage, talking on the phone. He had on a camel-hair jacket, silk scarf and of course his perfectly arranged Robert Wagner hair. “Very good, goodbye,” he says, and hangs up. Suddenly his hand shoots up and touches the right side of his head, where the phone receiver may have disturbed a few hairs. At that point you know he has done this smooth move every day since 1948.

Playboy: You seem to prefer goofy celebs – Jack Lord, William Shatner, Robert Stack. There are photos of Stack and Adam West, TV’s Batman, here in your office. Do those guys know you’re making fun of them?

O'Brien: I’m not. I have real affection for those men. To me, meeting Andy Griffith is just as interesting as interviewing Allen Ginsberg. I’m interested in Martin Scorsese and Gore Vidal as well as Jaleel White, TV’s Urkel.

Playboy: How do Gore Vidal and Urkel compare?

O'Brien: I’d say Jaleel White’s prose style is not taken as seriously. But then the same is true of Vidal’s nerd character.

Playboy: As one of the writers on The Simpsons you helped create some memorable characters.

O'Brien: What I loved about The Simpsons was that it wasn’t a cartoon for kids. A cartoon might look like the friendliest thing in the world, but we were subversive. I loved it when we had Lisa write a patriotic essay in school: “Our country has the strongest, best educational system in the world after Canada, Germany, France, Great Britain… .” It was this great sugarcoated cutting remark. I loved her for it.

Playboy: Tell us a Simpsons secret.

O'Brien: When Dan Castellaneta started doing Homer’s voice, he was doing Walter Matthau. Like I said, it takes time to find your rhythm.

Playboy: Are you satisfied with your work?

O'Brien: Intellectually, yes. The show works. Advertisers like to buy time on it. Young people really like it. But I was a moody, driven, self-critical person before I got this show, and that hasn’t changed. It’s just that I now have something even more frightening than a Saturday Night Live sketch or a Bart Simpson joke to worry about. I have an hour of comedy broadcast every night. My anxiety has finally met its match.

Playboy: Will you and Lynn get married?

O'Brien: The core idea of being a comic, particularly a comic with a talk show, is control. Marriage is a leap of faith, a giving up of control. I’m not sure I can make that leap.

Playboy: What about kids?

O'Brien: What sort of dad would I make? Maybe this job and a normal family life are diametrically opposed. Dave, Jay, Bill Maher, Arsenio – where are your kids? Jack Paar seems to have had a normal life with a wife and child, but you don’t see much of that. And I believe that your kid should be the most important thing in your life. I may not have room, at least not now. I have Pimpbot to think about.

Playboy: Another foulmouthed Late Night character.

O'Brien: Half-robot, half-Seventies street pimp. He’s got a feathered hat and a metallic voice: “Gotta run my bitches. Run my ho’s. I’ll cut you.” Right now my life revolves around Pimpbot.

Playboy: We need you to settle a fashion question. You, Leno and Letterman seldom wear suits offstage. Leno likes flannel shirts, Letterman prefers jeans and sweatshirts. You wear T-shirts. Why wear a suit and tie on the air?

O'Brien: There are two schools of thought on that. The Steve Martin approach says you’re putting on a show, so dress up for the people. The George Carlin approach says all that old showbiz stuff is over, this is the new way, so wear a T-shirt. I chose a jacket and tie because that’s the uniform people expect talk show hosts to wear. If I came out in a mesh T-shirt and chains it might distract people from the comedy.

Playboy: How would you describe your show?

O'Brien: It’s a hybrid. If Carson defined the talk show and Letterman was the anti-talk show, where do you go next? That was the question we faced. What we did was make a show that has the visual trappings of the classic Tonight Show – the desk, the band, the sidekick – but with everything else perverted. When it works well I’d say my show is one part Carson, one part Charlie Rose and one part Pee-Wee’s Playhouse.

Playboy: Do you have any advice for future talk show hosts?

O'Brien: You had better love the job. Some hosts don’t. You can see it in their eyes. Chevy Chase’s talk show – he did not want to be there. And if that’s in your eyes you’re finished, because there’s another show tomorrow and next week and the week after that. You can’t conquer it. You can do two or three or ten good shows in a row and still want to punch a wall when you slip up.

Playboy: Can you ever conquer your repressed childhood?

O'Brien: It’s always there. I still believe in moral absolutes. Murder, for instance, is wrong, unless it helps the show.

Playboy: Still, talk show hosts have perks most guys can only dream of.

O'Brien: It’s great to be “played over” to the desk. You finish your monolog, then the band kicks in as you cross the set. Fortunately, we have a great band. Even when people didn’t like anything else about the show, they loved the Max Weinberg Seven. The music heightens everything. Now you are more than just a guy in a suit, you’re Co-nan O'Bri-en! I think every guy should have that – if a band played you over to your rental car at the airport, you’d have a cooler day.

Playboy: Is Andy Richter your Ed McMahon?

O'Brien: He’s Andy. When we were getting started and the network wasn’t sure of me, they kept asking, “Who’s that Andy guy?” I think we’ve answered that question. Part of the show’s rhythm is my energy played against the quiet steadiness of Andy.

Playboy: Is that rhythm genuine?

O'Brien: Yes. Our mentalities mesh. I’m always dissatisfied. He’s the guy saying, “Hey, relax. It’s good enough.” My girlfriend would be happy if I had a bit more of that in me.

Playboy: Who is a guest you can’t get?

O'Brien: Werner Klemperer. He refuses to revive Colonel Klink, the commandant he played in Hogan’s Heroes. Which confuses me. Is he going to come up with another character at this late date – Werner Klemperer as the aging black man or kung fu fighter? No, he’s Colonel Klink.

Playboy: You once said that as a boy you wanted to be like Bob Crane in Hogan’s Heroes, the cool guy who “wore a bomber jacket and wised off to Nazis.”

O'Brien: I asked Werner Klemperer to do some bits as Colonel Klink. He refused. Then a strange thing happened. We’re shooting a bit on the West Side when Werner Klemperer comes around the corner. Pulling his parka up to his chin, just like Colonel Klink, he walks past our film crew and says, “Hello, Conan. I must say the show is very good lately. Give my best to Andy. Farewell!” It was a cameo appearance in reality. He was there, he was gone. I wanted to shout, “Hey, Werner Klemperer just did a walk-on in my life.”

Playboy: Are you losing the boundaries between your life and your job?

O'Brien: There are no boundaries. At any minute Werner Klemperer may step in here and give me 30 days in the cooler. It’s getting surreal. Just this morning I’m going through the lobby


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