The Late Conan
O'Brien
The strange story of how an odd-looking, oddly named regular
guy raised his show from the talk-show dead by learning to be himself.
By James Kaplan �-- �New York Magazine �-- �September 21, 1998
The summit of the talk-show mountain is strange territory. Among other things, it is a notoriously solitary place. A story Conan O'Brien tells me about David Letterman underlines this.
When I -- somewhat na�vely -- ask him whether he's friendly with the man he succeeded as host of NBC's Late Night, O'Brien shakes his head. "I really don't know Dave very well," he says. "When I first got the show, he called me up. There's a formality about him. Sort of an old-world gentility. He said, 'I'm not sure we've met. Have we met?' And I said, 'No, we haven't really met, Dave.' He was very nice. And at the end of the conversation -- I just couldn't help it, because he's such a big influence and everything -- I said the thing you're not supposed to. You know, 'It meant so much to me that you called; I'm a huge fan of your -- ' and I don't think I even got to finish the sentence. �He said, 'Well, that's not why I called.' "
It's a late-summer Thursday evening, and we're sitting in a restaurant off Columbus Circle. O'Brien looms in his banquette. With his big, chiseled cranium, sizable triangular nose, small, slightly upturned eyes, and incipient gut, the 35-year-old talk-show host can, from certain angles, bear a weird resemblance to the young John Wayne. But -- when he's not grinning his incandescent grin -- there's another resemblance: to a lost, sort of goofy-looking kid.
"It's funny," O'Brien says, a little wistfully. "Actors hang out together. Even stand-up comedians hang out together. Talk-show hosts -- none of them hang out. I wish there was, like -- at the end of Quincy, every episode, Jack Klugman would go to his bar, and the police detective and everyone -- the murder victim -- everybody would be there, laughing. I've always longed for a place like that in my life. We'd go at the end of the day and" -- he goes into jolly talk-show-hosts-letting-their-hair-down voices -- " 'When you asked Tony Danza if he was going to keep up this tap-dancing shit, I thought I was going to die.' 'Can we get more Buffalo wings over here, Luigi?' Letterman walks in. 'Dave!' 'Hiya, fellas.' 'Who did you have tonight?' 'Oh, don't even ask.' 'Who was it?' 'Alicia Silverstone.' 'Oh, my God. I'm sorry.' "
O'Brien smiles -- faintly. Still, the thought intrudes: What does he have to be wistful about? After all, over the past half-decade, he has taken NBC's Late Night from a bring-out-the-defibrillator-paddles start to a resoundingly successful fifth anniversary (to be celebrated with a prime-time special on September 16); last year, he signed a five-year, $2 million-per-annum contract with the network.
"Once your profession is being upbeat, you're screwed," O'Brien says. "There are two things that people say to me more than anything else. One is 'My God, I didn't know you were this tall.' " (He's six four.) "And the other is 'What's wrong?' Well, nothing's wrong. I'm 100 percent Irish. I'm depressed. You know? I'm genetically supposed to be living, like, in some marshy bog. Eating roots. In Ireland."
Yes and no. The mystique of Jack Paar and Johnny Carson and David Letterman has stemmed, in successive eras, not only from each man's comic genius but from our deep sense of the remoteness, the essential personal untouchability, of each. Garry Shandling's lacerating portrayal of Larry Sanders drew its power from this archetype.
But Conan O'Brien diverges from it. "My theory is that you had Carson, then Letterman came along and did the anti-talk show," he says. "I've always said that Letterman was like the Viking that found North America. And the rest of us are trying to carve out some virgin territory in northwest Oregon."
Letterman trumped Carson's slick if slightly cynical agreeability with an accelerating aesthetic of discomfort and showbiz deflation that made for fascinating viewing, yet ultimately lost him the job as Carson's successor on the Tonight Show. And O'Brien knew better than to try and take Letterman head-on.
"I think, because of Larry Sanders and everything, people love to see the inner workings. When you used to watch Johnny Carson and Charles Grodin would come out there and deconstruct it, it was hilarious, because you hadn't seen that done before. And when Letterman used to be self-conscious about there are cue cards here, and he started grabbing cue cards, it was fun at first.
"The problem was that once you do that, it's over. When guests come on sometimes and they talk about how they did a pre-interview and wink at the audience, and they grab the blue card and say, 'Yeah, yeah, we did these questions,' it's a dead end. That's all been done. And so the whole attempt of our show is, we're not going to deconstruct the talk show anymore. We're going to really do it. This isn't Larry Sanders -- as much fun as it is to watch Larry Sanders. This is the real thing."
"But also," I feel obliged to point out, "Garry Shandling's character on the show is this incredibly bitter, angry, insecure guy. Which is not you."
Conan O'Brien raises his eyebrows. "Well," he says. "You hit a few."
On the face of it, he is the most affable of men, spectacularly undefensive and continually, hilariously, generously funny. Unlike many other comedians, O'Brien doesn't sit around in his off-hours looking as though he'd just as soon strangle you as tell you a joke; and unlike virtually every other professionally funny person in the world, he gets almost no comic mileage from meanness. How he brings this off is a reasonably deep mystery. His humor is neither insipid nor sentimental. It has plenty of bite. It simply lacks bile. "I'm not the king of beautiful one-liners," he says. "The biggest thing that's in my family, that I think is in our bloodline almost -- it's very Irish -- is visual. That's what my brothers and sisters do, too. It's sort of absurd imagery. And I always like the show to be visual."
From the start of his tenure on Late Night, and with the essential collaboration of his friend and former head writer Robert Smigel, the show's best bits have always had a giddy, visual lift, as well as a certain wholehearted directness: "In the Year 2000" (in which O'Brien and sidekick Andy Richter don black cowls out of a cheesy science-fiction movie and make ridiculous predictions); the Clutches (blown-up photographs of news figures speaking with "Clutch Cargo"-like, computer-superimposed mouths); the Staring Contests between O'Brien and Richter; and many others.
Call it millennial anti-cynicism. The success of Late Night is built on having struck a chord with 15-to-25-year-olds who want no part of their elders' bitterness at the demise of sixties ideals, seventies sex and drugs, and eighties materialism. And while O'Brien may have made a smart artistic decision, it works because it's him. With Carson and Letterman one has always had the feeling that each man considers personal happiness fundamentally impossible; with O'Brien you get the sense that he thinks he has a shot at it. Maybe.
What else, after all, is to be made of an improbably pleasant childhood, in an upper-middle-class family on the edge of a blue-collar neighborhood in Brookline, Massachusetts? O'Brien was the third of six children in a household where humor and intellectual achievement were valued equally: His father, Thomas, is a renowned microbiologist; his mother, Ruth, is a retired lawyer.
"If you looked through our family history for thousands of years, you'd never see anybody remotely connected to show business or entertaining," he says. "I mean, we were as far as you could get from it.
"So I used to get attention for writing plays in school and being funny and everything. But I just remember thinking, You don't do that for a living. I sort of make fun of the idea of people saying, 'I always wanted to be a talk-show host.' Because who would really say, 'I always dreamed of interviewing B-level celebrities. And then going to commercial. And working for General Electric'? I mean, that's kind of a sad ambition." He smiles.
"My dad once said that being funny is probably some sort of neurological deficit," O'Brien says. "Your brain is making connections that aren't supposed to be there. He said probably at some point they're going to run people through a CAT scan and go, 'Yeah, you see, there's a problem here.'
"But the flip side of making those connections quickly is, you can think yourself into a depression really quickly. The same thing that allows me during the show to hear what they say and go, Wait a minute, but -- and come at it from a completely different angle, and make everyone laugh, also, when I go� home, enables me to see when a glass is falling over and go, Broken glass -- I could have cut myself and then I wouldn't be able to do the show. But at some point, I won't be able to do the show anymore because people will get sick of me. Why are people getting sick of me? Dammit, why is it over? I can't believe we got canceled. Next thing I know, my girlfriend's shaking me. 'You didn't. Everything's fine.' "
Anxiety, compression, and decompression, four nights a week, 45 weeks a year. How long can a human being live with this?
"Well, that's where alcohol comes in," he says. �
O'Brien appears utterly uninterested in the trappings of money and fame: He dresses from the Gap. He lives in a rented Upper West Side apartment with Lynn Kaplan, a former talent coordinator for Late Night. He seems optimistically intrigued by the possibility of having children. He has a new golden-retriever puppy named Hudson ("After my favorite movie, Hudson Hawk"). He owns an octagonal house in the Connecticut countryside and is erudite enough to drop the name of Orson Fowler, the nineteenth-century eccentric who invented the octagonal house and believed the structures possessed sexuality-enhancing powers. "That doesn't apply to me," O'Brien says.
He takes a sip of wine. "Jerry Seinfeld said something that I thought was very true -- people that think they're good-looking aren't funny," he says. "The thing I liked about that quote was that now I'm six four and 190 pounds, and they put some makeup on me for TV, and they put me in these nice suits, and occasionally women will write in and say, 'You're really good-looking.' That's not my self-image. Because in adolescence I was six four, 155 pounds, and had bad skin. "I don't say that in a self-pitying way. I wasn't a great athlete. I didn't really know where I fit in, or what it was I did well. People hear I went to Harvard, and they think, Oh, he must have been such a smart guy. But I actually think I ended up in Harvard because I was one of the winners of this national creative-writing contest -- I was kind of an interesting guy to them. I wasn't some SAT jock.
"I'm not the best-looking guy in the world. I'm not the most gifted. The only thing that ever really came easily to me was comedy. I could always make people laugh."
For almost a decade after he graduated from college, those people were primarily other comedy writers. "There are writers who are really good in the room, and then there are writers who don't say anything in the room, and then you send them off and they'll write a brilliant script," O'Brien says. "I was always known as a room guy. I would stand up on furniture, and I would perform. The analogy I always use to explain to people who don't know that world is, I was Buddy Sorrell in The Dick Van Dyke Show."
But the distance from Buddy Sorrell to Alan Brady -- between being a room guy and being host of a nationally televised broadcast -- is a chasm. There are a lot of room guys out there. And even as cable outlets proliferate, and more and more people become talk-show hosts all the time, most of them are certified performers, almost always stand-up comics. Quite simply, this is the easiest buy for executives to make. Johnny and Jay and Dave and Arsenio were stand-ups, the logic goes. The clubs are crucibles. This is what works.
Conan O'Brien's April 1993 audition to replace David Letterman took place, poignantly enough, on the Tonight Show set at NBC's Burbank Studios. Poignantly because, in the spring of 1993, there may have been about a half-dozen people in the world -- and that's being generous -- who thought that a gangly, red-haired comedy writer with next to no performing experience, a man who had never done stand-up in a comedy club, had a snowball's chance in hell of taking over the East Coast counterpart of this venue, NBC Studio 6A at 30 Rockefeller Plaza.
And in fact there is about the taped proceedings a strong whiff of let's-put-on-a-show, as though the tall young man in linen jacket and rumpled jeans, who was just about to turn 30 but looked much younger, had just stepped off the stage of some college talent extravaganza. O'Brien's tie looked as if it had been tied too tight, by someone else. (It had been.) His hair hung over his forehead in a sassy quiff. He walked out into the bright lights grinning, blinking, and chewing gum, and said, "Let me explain why I'm here. � This is the result of a drunken wager between [the new Late Night executive producer] Lorne Michaels and [NBC West Coast president] Don Ohlmeyer . . ."
He didn't stop there. He hit the note again and again, as if to emphasize to the NBC executives who would watch the tape how inappropriately unafraid he was. "It's very important to me that I get this job -- and I will say that right to camera," he said, staring straight into the camera. "I have to get this job because in a few years, like most Irish-Catholic people, my head is gonna get very wide, and fat, and red . . ." He paused as the studio audience, composed mostly of friends, laughed appreciatively. Then he gazed into the lens once more and sighed: "Oh, I like it here."
The line wasn't scripted. Before the audition, he'd had roughly the same opinion of his chances as everyone else. But all at once, the one person who believed most deeply in Conan O'Brien, in contravention to all good sense and industry opinion, was O'Brien himself. He may not have been a stand-up comedian, he may have made his name as a writer, but what he remembered at that moment was how strongly he had known since the age of 10 -- when he'd announced to his startled parents, utterly out of the blue, his desire to take tap-dancing lessons -- that he wanted to perform in front of an audience.
He knew it at Harvard, where, while he served as president of the Harvard Lampoon (the first person to do so two years in a row since another writer-comedian, Robert Benchley, 70 years before), he emceed rock concerts with wry repartee. He knew it when he moved to Los Angeles after college and studied improv (then performed with a troupe called the Groundlings), even as he worked a day job writing for HBO's Not Necessarily the News. He knew it when, after the 1988 Writers' Guild strike interrupted his work as a writer for SNL, he went to Chicago and helped write, and performed in, a comedy stage production called Happy Happy Good Show.
"The show wasn't a really big success," O'Brien says. "But I was so happy. I loved going out in front of people. I loved being in a show."
What Late Night producer Jeff Ross remembers most sharply about the early auditions for the new host is a persistent sense of surrealism. "There was a night at the Improv when they were auditioning every comic known," says Ross, a small, tan, natty man with a deep voice. "You knew who most of these guys were -- and they were all guys -- and nobody had any real strong opinion about anything. And Lorne, to his credit, his attitude was, let's get somebody who's smart, who's funny, who has a point of view. And if the network gives them a chance, it might work."
But who was that somebody? "I felt you had to drop down a generation," Lorne Michaels says. "The people who are up at 12:30 -- the core of it is ages 15 to 25. It's easier for them to relate to someone who's 30 than to someone who's 50. Just as Dave had been interesting because the model was Johnny Carson, you had to go younger and find someone who was really interested in doing an original show. And once I began thinking about who was that age, there were no qualified people."
Michaels did, however, have someone in mind to be the show's writer-producer: Conan O'Brien. "He was the only person I talked to," � Michaels says. "I was looking for a creator more than a host. I thought, If I can put the team together, we'll do a show that's not an imitation."
O'Brien was living in Los Angeles at the time -- early 1993 -- and putting his life back together. Nineteen ninety-one had been his annus horribilis: In quick succession, an engagement to be married fell through; a sitcom pilot he created with Robert Smigel wasn't picked up; and, burned out, he quit Saturday Night Live. His self-esteem was so shot that when The Simpsons called, he wasn't sure he was up to the job.
But after a year, he was happy again. He was doing his best writing ever in The Simpsons's best season; he had become a supervising producer of the show. With the help of an old Groundlings friend, Lisa Kudrow, he'd found a nice apartment. And then he and Kudrow became involved. He liked L.A.; he felt he could stay there.
When Michaels called about the producer-writer job, O'Brien remembers, "I had a big anxiety attack -- it just didn't feel right. I'd gone through this chaotic period, then done The Simpsons and gotten happy. Why would I jump into this situation when I knew whatever replaced Letterman would be in for a bumpy ride?"
After he backed out, he felt an immediate sense of relief. Then, a couple of weeks later, Michaels called again. Did O'Brien want to audition as host of Late Night?
"I wasn't thrilled," he recalls. He phoned Smigel, back in New York, to ask his advice. "Robert said, 'Ooh, boy, that'd be a really tough way to get into show business.' "
Lisa Kudrow disagreed. "He's the smartest person I've ever met, the funniest person I've ever met, and he's also the best conversationalist," she says. "At any party, you can seat him with any group of people and get them talking. So the more we would talk about how these [stand-up comics] weren't right, the more I started to say, 'You should be doing this -- you're the one.' But he wouldn't allow himself -- he felt like, 'No, I'm a writer, I just have to be happy with that; they won't want me.' "
"I thought, That's the girlfriend who's being overly flattering," O'Brien says. "My reaction was the same that America would have a few months later -- what business does this guy have hosting a talk show? So I've always understood that reaction."
Jeff Ross had roughly the same reaction. Until his first meeting with O'Brien. "I was living at the Four Seasons, and Conan lived nearby, so he walked over. We met in the lobby. They had this room with couches and an unused desk, and when I came in, he was standing behind the desk with a big grin on his face. 'Whaddya think?' he said. It was the craziest thing I've ever seen."
"What was so crazy about it?" I ask.
"That he had this confidence. That was the craziest thing."
Late Night with Conan O'Brien, show no. 1, on Monday, September 13, 1993, began with a very funny remote sequence of a breezily nonchalant O'Brien walking through Manhattan to his first day on the job as everybody -- his doorman, the guy at the newsstand, schoolkids, even a horse pulling a hansom cab -- says the same thing, over and over: "Better be as good as Letterman! Lot of pressure!" Smiling, whistling, O'Brien strolls into his dressing room -- and rigs up a noose. The on-air call comes just as he's about to slip it around his neck.
"I gotta admit that this is a little unusual," he said at the top of his first monologue. "I mean, let's face it -- most guys who are in this spot, they came up here in a different way. A lot of guys -- they spent years and years and years in the clubs, working very hard, and finally they get here on TV. My plan is to start here on TV, claw my way into the clubs" -- a big laugh from the audience; O'Brien smiled and teed off the capper. "Ten years from now, I wanna be in high school."
But there was something wrong on the first show, a faint but pronounced change from the audition. "Just before I went out onstage for the audition, I remember thinking, What the hell do I have to lose?" O'Brien says. "But auditioning for the show was much easier than doing the show for the first six months. Because then I worried about losing my network TV show."
He had good cause for worry. His nerves translated, on the first broadcasts, into a forced, fast, showbizzy style; he somehow resembled Steve Martin playing a talk-show host. Suddenly, O'Brien was doing something he'd never done before -- trying too hard.
Almost nobody, at the beginning -- not O'Brien, not Lorne Michaels, not Jeff Ross, certainly not the network -- was filled with glowing confidence that the show would last very long. Michaels saw one bright side: "Since it was also my ass, if my choice ended up just being a sorbet between a pro and another pro, it would be over quickly."
It was like the tale of Scheherazade: At first, the network would renew the show only in thirteen-week increments. The audience numbers at 12:30 a.m. are minuscule to begin with; Late Night was gasping for tenths of ratings points. "A couple of months into the show," O'Brien recalls, "Don Ohlmeyer did something that I actually thought was cool. He said, 'If your show climbs two tenths of a point in the next sweeps period, you will stay on the air. If you don't, I have to move on.' I'll never forget it. But I didn't mind that. Because I thought, All right, you're telling me. People I don't respect are the people who tell you to your face that you're doing a great job, and are secretly trying to replace you."
There were plenty of those, too. At the very first, Lorne Michaels recalls, "some of the press were empathetic." A lot of this had to do with Chevy Chase's widely reviled, short-lived talk show, which had come on the week before and taken a lot of the pounding. "Conan wasn't important enough to be destroyed, just dismissed," Michaels says. "But then the reviews got vicious, and there was a lot of intrigue on the West Coast. People were saying we should get rid of Andy [Richter], and all of it."
O'Brien somehow managed to be the calm eye of the storm. "What's funny is that I was oddly suited to all the trouble that I went through the first two years," he says. "That might be Catholicism. Maybe some sort of self-flagellating -- you know, 'I deserve to have a difficult time.'"
He laughs. "I was an unusual kid in that way. In the third grade, I kind of felt like I was under the gun for some reason. I had this feeling of, like, 'You gotta be good, you gotta be good.' Even my little crappy papier-m�ch� volcano -- you know, 'It's gotta be good, it's gotta be good.' When I was on the Lampoon, 'It's gotta be good, it's gotta be funny.' At Saturday Night Live, I was behind the scenes, but I felt a lot of pressure. Like, 'Oh, Tom Hanks is here. I've got to think of a really good idea for Tom Hanks.' Replacing David Letterman, who had influenced me, who I had such respect for -- that was such a surreal amount of pressure that at a certain point you kind of don't feel it anymore. It's like the needle doesn't go any higher, and that's kind of liberating, almost."
Almost. "I was a guy trying to do a good talk show," O'Brien says. "A smart guy, and a nice guy, but trying to do a good talk show. And you don't ever want to watch somebody trying to do a good job at comedy. That's not fun. That's never what made me funny. What was always funny about me was just stuff that I said when I was happy and enjoying myself. I just had to make all that other stuff become mundane -- the lights and the people and the network and the advertisers. And that took a little time."
By most accounts, it took a year and a half. In the meantime, the comedy, though scintillating, felt overbearing. O'Brien spent so much time rehearsing the bits that sometimes he wasn't prepared for guests. Routines were occasionally designed to interrupt interviews. It didn't feel respectful, and O'Brien didn't feel totally in control. The souffl� wasn't rising.
Slowly, he figured it out. "After a while, he began to stop doing what made him look uncomfortable," Michaels says. "He started letting guests talk, not letting bits go on too long. More and more, he made it his show."
Meanwhile, though, "the network was less than supportive, and the network was behind the curve," Jeff Ross says. "I believe for the first year, year and a half, they were consistently looking around to see what they could do [to replace O'Brien]. We had to survive by scratching and clawing." They bargained for their lives by settling for shorter renewal intervals. "We had to go work the press, we had to go get publicity, we had to go to the people who thought the show was good and have it written about."
Lorne Michaels remembers a dinner with Ohlmeyer "when the show was stalled -- things were flat, and there wasn't enough [ratings] growth for anybody to be cheerful about. And I said if it wasn't gonna happen, we were owed like three months, because it'd be very abrupt to cancel right away. And Don said, 'Come on, he's our guy.' "
Ohlmeyer had taken note of an interesting phenomenon. "Michael Zimberg, who was an executive at NBC Productions on the West Coast, went up to see his kid at college in Boston, and they were all talking about Conan in the dorm," Michaels says.
The show was finding its audience. Late Night went through a temporary wobble in January 1995 when Robert Smigel, feeling burned out, quit as head writer. Two other writers, Alec Berg and Jeff Schaffer, left around the same time to go earn bigger bucks on Seinfeld. But the departure of Smigel was double-edged. "Conan and Robert were peers when the show began," Michaels says. "But more and more, Conan moved into a much clearer sense of command. By the time Robert left, it was very much Conan's show."
By nature as a writer and a nice guy, O'Brien was a consensus-builder. But it's a show-business clich� -- and axiom -- that no matter how good the support staff is, everything comes down to the host. And -- even though he was no less a writer or nice guy -- Conan O'Brien had finally become what he was meant to be.
Noontime in Conan O'Brien's office: O'Brien, in his offstage uniform of Gap khakis and polo shirt, strolls around, noodling on a Gretsch guitar. He's a pretty good guitarist: He plays a convincing Ventures lick as his assistant microwaves him a special low-fat lunch. "I had my cholesterol tested, and the nurse offered to walk me back to my car," he says. "It's an occupational hazard. Comedy writers are the only people that think eating General Tso's chicken and pork fried rice is healthy."
O'Brien's smallish office, a corner with sweeping views down Sixth Avenue and out to the Hudson, is prodigiously cluttered with objects and memorabilia both funny and sincere: A giant pickle. A small statue of George Burns. A model parade float containing Uncle Sam and a beer mug, reading DRUNK IS GOOD. A large photo of O'Brien on the set, looking pleasantly stupefied that his guest is Ted Williams. A huge nineteenth-century lithograph of Abraham Lincoln's deathbed. A basketball backboard with a horror-movie flayed head, wearing a coonskin cap, stuck upside down in the net. An autographed eight-by-ten glossy of Andy Richter, reading, "To Conan -- your bitter jealousy warms my black heart. Kisses, Andy." Photos of his girlfriend. A picture of his new puppy. A panoramic photo of his octagonal house. A framed letter from Jack Paar, thanking O'Brien for his introduction at a tribute to Paar.
"I hear good things about your program and I am sure that one day you will inherit the 'Paar, Carson spot,' " the letter reads, in part. "I was impressed by your manner, never lose that natural, intelligent speech pattern. I really think you will go all the way. Save your money, marry a nice girl, get a dog, and buy only blue shirts. . . . I could have gone even farther if I had your hair. . . ."