Conan O'Brien's Three-Year Overnight Success

What's he got that you don't? A Harvard degree, nearly $2 million a year, supermodel neighbors, an annoying laugh and the hottest comedy show on TV

September 19, 1996
Conan O'Brien
Conan O'Brien on the cover of Rollin Stone.
Mark Seliger

You can call it fate or you can call it breaking and entering. The differences are marginal. The time was the late '80s, a simpler period somewhere before the fall of the Berlin Wall but after Billy Squier had taught us "The Stroke," a time when the phrase "late-night wars" had yet to be invented. Back then, while David Letterman was quietly building an empire in the hours past midnight, a young Harvard grad named Conan O'Brien was making his way as a writer for the recently resuscitated Saturday Night Live. Every now and then, to get a break from all-night writing binges, O'Brien would sneak downstairs, pick the lock to Studio 6A, pull the tarp off the host's chair and attempt to write comedy while sitting at Letterman's desk. "It wasn't like, 'Someday I will sit here,' " says O'Brien. "It was more like, 'This is where he sits? Cool.' " He laughs – you know the sound: high-pitched, slightly braying – and continues. "Really, the point of the story is that NBC has terrible security, and I'm sure now every night there will be a different weird person sitting at my desk."

It is sunday afternoon, the day before the staff is to return from vacation, and the 33-year-old O'Brien, all 6 feet 4 inches, obsessed workaholic of him, has come into that very studio to assess the new set that has been built for his show. His show. Gone are the tacky, Ikea-style desk and cheap paneling. In their places stand a plush new couch and a kind of festive blue-and-purple wall ornamentation that suggest O'Brien is enough of a network commodity to warrant a set that looks a bit like a brothel.

O'Brien walks around the couch, idly strumming an electric guitar, telling stories and making suggestions.

"The carpet has to go," he says. He pauses, as if this has been too demanding. "Don't you think?" And then, perhaps remembering he's the boss, he answers his own question. "We need to make sure it's gone by Tuesday."

He strums some more and wanders into his dressing room, where an all-too-large picture of Robert Stack stands guard over a punching bag, a Nautilus machine and a pile of rockabilly CDs. He sets down the guitar. The studio and dressing room are still the temperature of an ice-cream truck, but that is the only noticeable nod to the Letterman legacy. These days, as O'Brien nears his third anniversary and the show celebrates its first Emmy nomination for comedy writing, O'Brien is more in competition with himself than the ghosts of talk shows past.

This is not a story of Conan O'Brien, happy accident. It is the tale of Conan O'Brien, paradox: professionally goofy but with a work ethic that he calls "almost humorless." He was the editor of the Harvard Lampoon for two consecutive years. When he left SNL to become a writer for The Simpsons, producer Lorne Michaels – who also hired him for the Late Night job – kept O'Briens office empty, his name still on it, for a full year, just in case he might return. O'Brien is both a pathologically serious soul and a pointedly funny writer and performer. He has always been focused – working 12- to 16-hour days, decompressing just enough to enjoy a Saturday evening off, then setting his mind to worrying again by Sunday night – but now the show is reaping the benefits of his neuroses.

"Until now, all my life, professionally, it felt half-right, but it wasn't exactly what I wanted," says O'Brien. "So when this show eventually stops and is replaced by an hour of country & western music, it'll be difficult for me to do something different. I don't know what I could do to make me this happy."

He falls silent for a moment.

"Fortunately I didn't think about it too much when things were real rocky," he adds.

The first time we ever saw Conan O'Brien on the air, he was strolling cheerily to work for his debut while every passer-by taunted him with, "You better be as good as Letterman." Children, old ladies, even horses: "You better be as good as Letterman." When he finally arrived at the studio, O'Brien sauntered happily to his dressing room, took out a noose and started to hang himself, only to have a stage manager show up.

"You're on, Mr. O'Brien," the stage manager said.

O'Brien looked at the man and asked, "Now, or do I have a minute?"

The man was emphatic: "Right now." O'Brien shrugged, removed the noose and took to the air.

It didn't take long, however, before NBC executives were wondering if they should have given him a little extra time to himself. That laugh. The nervous tics. That sidekick. Those ratings. The only positive attribute ever noted in the show's early daze was a daring array of musical acts, but that was not enough to quiet the rumblings. Rumors of cancellation popped up more often than high-fives at a frat party. When NBC hired Greg Kinnear to host Later, the show that follows Late Night, most people assumed that O'Brien was, at best, a seat-warmer for the snarky pretty boy. "I'm afraid to say we probably don't know how close we were to getting canceled," says Late Night producer Jeff Ross. "Part of me has a morbid curiosity. I think we got a lot closer than we think."

But all of that was nothing compared with the barrage of personal insults that awaited O'Brien and his sidekick, Andy Richter. It wasn't so much that critics didn't like the show, they just plain didn't like O'Brien and Richter.

I have heard every euphemism for fat," says Richter, a veteran of the Chicago improv scene. "It's incredible. They don't say, "The black actor Denzel Washington,' or, 'The medium-build Kevin Costner,' or, The small, Jewish Dr. Ruth.' But they say fat, chubby, portly, cherubic. All of which is fairly emasculating."

Still, the noose stayed in the briefcase. O'Brien's friends and family stress that, yes, it was a dark period, but, no, his confidence never waned. "The lows were probably as low or lower than people might think," says his sister Jane, a writer on Cybil. But what became clear is that although it's gut wrenching to read attacks in the press, at least his name is in the paper. Which means he must still be on the air.

I'm a realist," says O'Brien. "I live in America in the 1990s, and I entered the ring of pop culture. I'm not going to lie to you. The criticism hurts. But what really saves you is that you have a show to do every day. You don't have much time to sit around and say, 'Maybe my laugh is awful, and maybe I do fiddle around too much; maybe I am awkward.'"

And then a funny thing happened on the way to extinction. Several, actually. Like Devil-Bear, a sketch in which O'Brien receives advice from a devil on one shoulder and a bear on the other – except that the bear is only able to give tips like, "When scratching yourself against a tree, do not use a pine tree or you will get all gooky." And remote segments from events like 1994's Woodstock concert and the MTV Video Music Awards, in which the overweight Richter has consistently proved himself to be one of the show's most invaluable assets.

But the biggest difference is O'Brien himself. Where he once appeared more shocked than the rest of us that he was actually on television, now he is comfortable. The program was always intended to be a bizarre sketch-comedy show that just happened to include interviews – a type of alternative universe where men dressed up as flowers dance on the Brooklyn Bridge – and a large number of the show's original staple comedy pieces (In the Year 2000) continue to be used." All the plates were in the baby's skull," says O'Brien. "They just hadn't fused yet." Viewership is up 18 percent from the first year, and Late Night's audience has a higher percentage of 18- to 49-year-olds than that of Leno or Letterman; Washington Post TV critic Tom Shales, who once called for O'Brien's big-haired head on a stick, is now the show's staunchest supporter; and for the first time, NBC has ponied up the cash for an anniversary show.

Then again, Late Night draws its guests from the celebrity JV squad and is still capable of missing wildly. On any given night, viewers might wonder what cable-access staff has taken the NBC studios hostage (the recent Nerdy Guy on Pommel Horse at the Beach springs to mind). But the laugh-to-cringe ratio is high enough to warrant a little forgiveness. Not to mention that O'Brien has turned into an excellent interviewer; He actually listens.

"I think the home audience needed time to trust Conan," says original head writer Robert Smigel, a friend of O'Brien's since they were writing partners at SNL. "We had sort of a cocky attitude. We really set out to do weird stuff. We just wanted to blow people away with how different the show was. But it is really about the host and about trusting the guy."

Talk around NBC initially centered around placing that trust in Garry Shandling, but that quickly fell through. Ironically, O'Brien was asked to be the show's producer and briefly helped search for a host before executive producer Lorne Michaels finally gave in to O'Briens suggestion – "How about this Conan guy?" – and called to inquire if he'd like to audition himself. In the end, O'Brien was the only person screen-tested.

"When I got this assignment, I thought I would not be predisposed to like the guy who replaced David Letterman," says O'Brien. "So I probably wouldn't have given me high marks in the beginning."

He laughs – you know the sound – and then continues: "But now I'd really be into me."

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