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Playboy Interview: Conan O'Brien
  • December 12, 2010 : 07:12
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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.

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