Playboy Interview: Conan O'Brien
a candid conversation with the preppie prince of "late night" about his rocky start, his show's secret one-day cancellation and how David letterman saved the day
interview by Kevin Cook �-- �Playboy Magazine �-- �February 1998 �-- � Pgs. 51 - 58 +�
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He was polite. He was funny. He gave us a communicable disease.
At 34, Conan O'Brien is hotter that the fever he was running when we met in his private domain above the Late Night sound stage. 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 is the head that wears a crown. Congested, too, but O'Brien has far more to worry about than his head cold. A perfectionist who broods over one bad minute in an otherwise perfect hour of TV, he worries that 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 old, 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 be 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'm a complete unknown," he said. That line got a laugh, but soon O'Brien looked 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 define's 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 an on air talent. In almost four years on the show, O'Brien made only fleeting appearances, usually as a crowd member or a security guard. His writing was more memorable. He wrote (or cowrote) 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 7-figure offer to continue as a writer.
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 David 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 multi-million 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 gave him -- 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 its all for show. From the photograph 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 visitors 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.
"Here's hoping we succeeded. If not, I carried his germs 3000 miles and infected dozens of Californians for no good reason."