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Conan O’Brien Comes Clean

He has overcome his depression and anger. Now the comedy genius is ready for one last late-night ride

Conan O'Brien performs during 'The Legally Prohibited From Being Funny On Television' tour in Eugene, Oregon on April 12th, 2010.Conan O'Brien performs during 'The Legally Prohibited From Being Funny On Television' tour in Eugene, Oregon on April 12th, 2010.

Conan O'Brien performs during 'The Legally Prohibited From Being Funny On Television' tour in Eugene, Oregon on April 12th, 2010.

Jackie Butler/Getty

In July, shortly after his Legally Prohibited From Being Funny on Television Tour wrapped up, Conan O’Brien began visiting the set of his new talk show, at Warner Bros. Studios in Burbank, California. For various reasons, the show had not been staffed yet, nor had the set been built, so on those days, O’Brien would occasionally pause en route to his office and stand alone in a giant, empty warehouse. As career metaphors go, one could do worse: At least the warehouse wasn’t on fire, or dripping blood from the ceiling, or filled, floor to rafters, with an existentially crushing number of identical wooden crates, like the warehouse at the end of Raiders of the Lost Ark.

O’Brien had lost his dream job as host of The Tonight Show in January, at a speed (seven months!) almost as humiliating as the circumstances of his departure (oust­ed for Jay Leno, which is the comedy-world equivalent of being left at the altar for a cast member of Jersey Shore). “My wife says those first couple of months, the thing I said most often was, ‘Wait a minute, what just happened?'” O’Brien recalls.

“Those weeks after the tour, where not much was going on, Conan was misera­ble,” confirms his wife, Liza Powel, a blunt and dryly funny former advertising ex­ecutive with whom O’Brien has two chil­dren. “That was when he was the most de­pressed.” Powel says she had “all sorts of grand designs” about keeping her idled spouse busy: He would be responsible for camp drop-offs, he would cook dinner at least one night a week. None of which ended up happening. O’Brien did go for long bicycle rides, and read lots of histo­ry books. At a parents’ night at their son Beckett’s preschool, there was a stack of volunteer sign-up sheets, and O’Brien, who still had too much time on his hands, became overly ambitious and started sign­ing up for everything: “Oh, I’d love to come talk to the kids about natural history!”

“He was in the house all the time,” Powel recalls. “I said, ‘This can’t last – it’ll drive us crazy!’ Literally every 10 minutes, he’d poke his head in the room and say, ‘I don’t wanna bother you, but do you know where the Band-Aids are?’ ‘I don’t wanna both­er you, but do you know how to use the phone?’ He was so sweet about it, and I felt like such a jerk. But seriously, I almost rented an office for him.”

The morning after O’Brien’s final Tonight Show – his second-highest-rated episode ever, quadrupling his average nightly viewership – he and Powel drove up to a resort in Montecito. “I felt like I’d just been in a car accident,” O’Brien says. “Like a crazy mix of elation, anger, sorrow. Con­fusion was a big one.” That night, when they entered the dining room and the other guests stood up and applauded, O’Brien says, “It almost made me cry.”

An overachieving golden boy since high school (where he was class valedictori­an), on through college (Harvard, where he was twice voted president of The Har­vard Lampoon, something that had only happened once before in the history of the venerable humor magazine) and his early career (staff gigs at Saturday Night Live and The Simpsons, the twin Holy Grails of the comedy world for the aspiring writ­er), O’Brien had been plucked from ob­scurity to host a major-network talk show – at a time when people still watched net­work television – when he was a preposterously young-looking 30 years old. Los­ing The Tonight Show was the first time he had ever failed so publicly, and in such epic fashion. His longtime sidekick, Andy Richter, has said, “It was traumatic for Conan.”

“I hated to see him in such a state of ten­sion and unhappiness,” Powel says. “It was very painful for him to let go of this hal­lowed ground that he’d finally got a chance to stand on.” But, she goes on, “There were so many factors at work, such a confluence of change that had to do with so much more than him. The truth is, The Tonight Show was the definition of cultural rele­vancy for decades. And all of a sudden, it’s not. That’s not Conan’s fault. It’s not any­body’s fault. It just happened. And it’s no longer a show he should be pinning his life’s hopes on hosting.”

Indeed, the spontaneous pro-Conan In­ternet campaign generated by fans in January – complete with Shepard Fairey-style iconography and its very own slogan, “I’m With Coco” – was driven largely by young people for whom the venerable institution of The Tonight Show meant little or noth­ing. For some, the show might have even made O’Brien less cool by association. The Tonight Show had been unhip for a very, very long time, not just for the past 17 years it has been hosted by Jay Leno, but for (let’s be honest) pretty much all of the Eighties – really, the last time it was hip, Johnny Car­son and his guests were still chain-smoking on the air – and so watching O’Brien move behind the desk of desks felt less like an ascension and more like a loss, a co-opt­ing of our guy. Conse­quently, when O’Brien was undone by NBC’s fecklessness and Leno’s treachery, it only affirmed what we knew all along: He’d thrown his lot in with the wrong crowd.

Overnight, O’Brien not only regained the underdog status he’d held for much of his ca­reer, but actually found himself in a wholly new position: rebranded as an indie icon. In the months that followed, he grew a beard, played Bonnaroo and cut an improvised spoken-word single and a rock covers album for Jack White’s label. (“Conan’s was the only late-night show I ever wanted to play,” White says. “Letterman is so cold to people, and Leno is for senior citizens. I played a live guitar solo on Conan’s desk once. If I did that on Letterman, he’d probably have had a coronary.”) When O’Brien announced his 30-city comedy tour via Twitter, with­out any traditional promotion whatsoever, it sold out in hours.

Of course, the soaring ratings during the last week of O’Brien’s Tonight Show can be attributed to morbid curiosity. Sudden­ly, celebrities who normally only show us their public personas were openly display­ing real emotions, live on TV. Had we ever seen O’Brien look genuinely hurt or angry before? Or, for that matter, Leno squirm like the night Jimmy Kimmel mocked him to his face? Or David Letterman display-such unadulterated schadenfreudean de­light as with his belittling impersonations of his old rival? It was reality television writ large, and riveting to watch.

But something else happened to O’Brien once he’d been denied his stay of execution. He got better: funnier, more confident, the sort of Tonight Show host fans always hoped he’d be. “When Conan took over, I thought he was doing a really good job, but I felt, sitting on the couch, that it wasn’t as intimate as the old show,” says his friend Garry Shandling, who regularly guest-hosted The Tonight Show in the Eighties and brilliantly played a fictional late-night host on The Larry Sanders Show. “Merely by cir­cumstances: It’s a bigger stage, a slightly different crowd. These dynam­ics are subtle.” Shandling says he noticed “something shifted” in O’Brien’s work once he knew he was leaving. “He got very loose those last weeks,” Shandling says. “He was more present, more honest. My acting teacher used to say, ‘Do you have the cour­age to discover something about yourself while the camera is running?’ That’s what makes great performances. And I think the reason Conan got so much attention at the end, and lit up the screen like that, is because he was discovering something about himself while the camera was on.”

When O’Brien left NBC, it was widely assumed he would take his show to Fox, which wanted to create its own late-night fran­chise and began courting him heavily. But when unlikely candidate TBS entered the picture, the network promised “the biggest promotional campaign in television history,” O’Brien’s manager told The New York Times. (TBS broadcasts professional-basketball and major-league-baseball play­offs, and has already unveiled a number of lavish promo spots and a Conan blimp.) TBS would also be giving O’Brien a strong lead-in for his demographic with reruns of The Office and Family Guy.

How, exactly, to capture the elusive spark of O’Brien’s Tonight Show swan song and subsequent tour and funnel it into anoth­er talk show is the challenge Team O’Brien now faces. When I met O’Brien at Warner Bros, in late September, his show, Conan, was a little more than a month away from its debut on November 8th, and there was a hivelike energy around his offices (still largely unfurnished) and on the set (still very much under construction). “This is the second stu­dio I’ve designed in 15 months,” O’Brien says. “I’m thinking I might get into build­ing studios instead of comedy. You know, I’ll be like a consultant: I can meet with you, get your vibe.”

O’Brien, who is 47, is primarily known as a verbal comic. But at six feet four, he has a physical comedian’s body: O’Brien is so long-limbed and gan­gling, it’s not a huge jump for him to transform himself into a giant puppet, as he does at the start of most shows, and his gaunt, expressive face possesses a clownish elasticity. (His sidekick, Richter, is short and stocky, rounding out their classical fatty-skinny comedy team in a way that O’Brien surely appreciates.) O’Brien loves to joke about his pasty complexion, and these jokes are not exaggerations. In per­son, when the light hits his skin the right way, it can look alarmingly, just-north-of-translucently pale, calling to mind a freckly parchment. His hair remains sculpt­ed in its signature half-pompadour, and he’s also held on to the beard, and wears it well, along with, this afternoon, a black leather jacket, black jeans, a tight navy-blue T-shirt and black Adidas sneakers, looking less like a guy who used to wear a suit to work every night than like a guy looking to score an extra Pavement tick­et. (O’Brien plans to keep the beard for his show, at least initially: “I think if I come back cleanshaven, it’s almost saying, ‘OK, that fun ride is over.'”)

O’Brien enters Stage 15, where his set is being built, striding past a couple of workmen laying down a wooden floor. No seats have been installed yet, and there’s no stage, either, just the beginnings of a curved backdrop and a cluster of oversize lights hanging from the rafters. O’Brien wants the new set to be tighter, with his desk in the middle, flanked by the band. “It’s almost like physics: The smaller the space, the greater the pressure,” O’Brien says. “Which is better for comedy. Those wide, arcing shots that make your set seem like a Leni Riefenstahl rally, with thou­sands of fans, those are OK for the first five seconds of a show. But then what you’re re­ally trying to do is something that’s quite small. Comedy is delicate. You’re chatting with people and creating funny little mo­ments.” We wander through the green­room into his dressing room, where anoth­er door leads directly to the set. “In case I don’t like the guest,” O’Brien says. “I call it the Pauly Shore Door.”

Then O’Brien, a cinephile who con­stantly references old films, excitedly leads me to the front of the building, where a bronze plaque lists all of the movies filmed on this very set: The Petrified Forest (one of O’Brien’s all-time favorites, starring Hum­phrey Bogart as a hostage-holding killer), Mildred Pierce, The Big Sleep, Strangers on a Train, Giant, The Music Man (an­other favorite, and the inspiration for one of O’Brien’s best-known scripts for The Simpsons, the one where an unscrupu­lous traveling monorail salesman attempts to hornswoggle the people of Springfield). “Look at this: It’s like the Vietnam Wall,” he says, grinning as he runs a finger along the list. “Some of the greatest films ever made, and then——” His finger stops at 1985, and his voice rises. “The Goonies! Did they really have to put that one on here?” He shakes his head. “People young­er than me love this movie. It’s their Cit­izen Kane.” At some point on the show, O’Brien hopes to reunite the cast.

The first time O’Brien lived in Los Angeles, he was 22. He’d moved out with his college friend and writing partner Greg Daniels, who would later create the American version of The Office. They’d worked together at The Harvard Lampoon. In L.A., they wrote for the HBO sketch-comedy show Not Necessarily the News and shared an apartment; if one of them had a date, they had to give the other a heads-up, because they also shared a car. (Though O’Brien says that this problem didn’t come up very often in those days.) O’Brien hated L.A. then, having what he calls “a stereo­typical Woody Allen reaction” to the city. He likes it now, and felt ready for a change after years in New York. “Is L.A. less edgy? Yeah,” he says. “A comedian said, ‘I used to hate L.A. Then one morning I woke up and something inside me had died.’ Maybe that’s happened to me.”

At the moment, we’re in Hollywood, en route to O’Brien’s first solo apartment. O’Brien is driving a gray BMW, wearing tortoiseshell sunglasses and a long-sleeve navy-blue shirt. He’s a careful driver, keep­ing both hands on the wheel. He’s also a nonstop talker. In the first years of Late Night With Conan O’Brien, he would occasionally cut off his guests, mid-anecdote, unable to resist injecting his own (admit­tedly, much funnier) joke.

O’Brien, noting how much cleaner Hol­lywood looks these days, launches into one of his long riffs. “I’m really good at living in a place eight years before it’s safe and cool,” he says. “In the Eighties, I lived in Williamsburg. That was when they just shot people in the head and took their under­wear. They stole things from you that they didn’t even need. ‘I wanna take his under­wear.’ ‘You have underwear.’ ‘I know.’ Blam. So a friend of mine said, ‘I have a space for you in my place in Williamsburg.’ And I remember thinking, ‘Ah, Colonial Wil­liamsburg.’ I actually had this image of cobblestones and gas lamps and people churning butter. But I was disabused of that notion really quickly. There was no hipster stuff at all yet. They have to para­chute hipsters into an area 15 years ahead of time, and many of them die, but they lay the groundwork. And I think that’s prob­ably what happened in Brooklyn. There’s a while where they’re pouring hipsters in and it’s like Gallipoli. It’s just troops get­ting mowed down. Just battalions of guys wearing Buddy Holly glasses and bowling shoes getting chewed up. But then eventu­ally they take over.”

We turn onto a residential street lined with stucco apartment complexes and pull over. O’Brien leads me to the gated alley of one of the shabbier buildings, point­ing out the window of his old room at the far end. “It was the kind of place,” he says, “where when someone takes a shot at the president and the Secret Service jumps on him and finds his address and 20 minutes later they kick down his door – that’s what my apartment looked like. ‘What kind of sick mind…?’ It had that kind of vibe. Criminologists would study it and say, ‘We should’ve seen it – he was a powder keg!” O’Brien lasted three years in L.A. dur­ing that first stint, and earned enough of a rep to get a job at Saturday Night Live. He would return in the early Nineties, when he was hired to work on The Simpsons.

When we drive past his Simpsons-era apartment in West Hollywood, it’s clearly an upgrade. “It was the second floor of that place,” he says, slowing down. “You can tell things are getting better now. And here’s the best thing. On the first floor, these two models lived there who were gorgeous. And I’m not even lying about this. I had the top floor, they had the bottom floor. And one day I’m in my apartment, and they’re taking photos of each other in the back­yard. And they have the silver reflectory thing, and they’re wearing string bikinis and giggling. I’m not even making this up. It sounds like Animal House or something. And I just happened to look out the win­dow and see them doing this, and sudden­ly I’m frozen like a deer. And they look up, and they see me looking down at them, and I’m so fucked. It’s like I’m Boo Radley. I’m the pervert on the second floor.”

It’s true: There are few ways to recov­er from that.

“No! I started shouting, ‘I’m not masturbating! I’m really not masturbat­ing!’ Which, I’ve found, is never a good sentence.”

Even if true, probably not the best thing to yell.

“First of all, it wasn’t true. Second of all, yes, it’s like Nixon’s ‘I am not a crook.'”

O’Brien calls his publicist to let him know our whereabouts. “It’s going terribly,” O’Brien says. “I’ve been telling him about my racial theories.”

“Oh, no,” the publicist says.

“I will be proved right one day!” O’Brien shouts.

There’s a famous magazine profile of Johnny Carson, which O’Brien loves, in which the writer Kenneth Tynan describes Carson as chatting at a cocktail party “with impersonal affability, making no effort to dominate, charm or amuse.” Tynan goes on to quote an acquaintance of Carson’s who says, “Socially, he doesn’t exist. The reason is that there are no television cam­eras in living rooms. If human beings had little red lights in the middle of their fore­heads, Carson would be the greatest conversationalist on Earth.”

O’Brien is not like this. Onstage or off, he’s always on, his mind racing several steps ahead of the conversational topic at hand to scout for possible bits. Which is not to say he’s a self-absorbed monologuist, like certain performers who grow used to doting audiences hanging on their every word. In fact, he’s unusually inquis­itive for an interview subject, and clear­ly enjoys having a two-sided conversation. But the joking does have a compulsive, al­most Tourettic quality, as if the only way for O’Brien to process the world around him is to incessantly, fanatically catalog its absurdities.

Another surprising detail about O’Brien: One of his closest friends happens to be a Catholic priest. “As much as I hate to give him credit, I think he is one of the few most uniquely funny people I know,” says the Rev. Paul O’Brien, the pastor of St. Patrick’s Parish in Lawrence, Massachu­setts. O’Brien and O’Brien (no relation) lived in the same house at Harvard (along with future NBC president Jeff Zucker, who presided over O’Brien’s ouster from The Tonight Show and was recently fired himself), reconnecting sever­al years after graduation when they bumped into each other at midnight Mass one Christmas.

“He loves entertaining the five people he’s just met,” Rev. O’Brien continues. “When we’ve been on vacation together and he’s relaxed and doesn’t have to worry about whatever show he’s on, it’s actually amazing how much funnier he is.” And how much of his comic sensi­bility is drawn from his Irish Catholicism? “Oh, everything,” Rev. O’Brien says. “Everything about him. Whether we like it or not, that’s what we’ve turned out to be. He has a dark humor that can be traced back to the Irish, and a respect for human beings where, while he may be lampooning them, he’s not hurting them. And like most of us who are Irish, he has an in­finite capacity for vengeance. The Irish-jihad potential is enormous! But if you channel it into something like comedy, it’s very powerful.

“The negative side of being Irish is that a Jewish person might say, ‘Oh, Conan, I knew him in high school, and now look how well he’s done.’ Whereas an Irish person might say, ‘Yeah, I knew him when he was in a cold-water flat in Somerville. He was nothing.’ That neg­ativity gives you the strength of humility. You’re not supposed to be the most impor­tant person in the world, and you don’t ever think that you are.” Rev. O’Brien laughs, and then says, “If his grossly misshapen head has ever become inflated, it wouldn’t stay that way for long.”

O’Brien’s office is modest and, like his set, still almost entirely undecorated. There’s a turntable, a couple of phones on the floor, nothing on the freshly painted walls. As O’Brien rein­vents himself for the second time in as many years, his surroundings seem set-designed to reflect the blankness of the slate he’s facing.

At the moment, Sona Movsesian, O’Brien’s assistant, is seated at his desk, attempting to load some backstage pho­tographs from his comedy tour onto his computer.

“I’m still waiting for it to identify the hard drive,” she explains.

“Oh, you failed us,” O’Brien says. Turn­ing to me, he adds, “Sona’s an Armenian immigrant.”

“I was born here,” she says.

“She came to this country weeks ago,” O’Brien says. “It’s not her fault. She learned to speak English by watching old episodes of Dynasty.”

“I was born in Montebello,” she says.

“That’s an island off Bulgaria,” O’Brien says.

O’Brien’s first months on Late Night were famously awkward. He was 30 years old, but looked like an intern wearing his only suit, and his caffeinated performance style came off as nervous and twitchy. “Conan’s a wired-up guy, and unless a performer has a-thousand-percent confi­dence, which he didn’t at that point, you can’t force his persona on the public,” says the writer Robert Smigel, who worked with O’Brien on SNL and later became the first head writer at Late Night. Still, al­most from the beginning, it was clear that O’Brien and his team were bringing a new, appealingly bent sensibility to the genre. Smigel wanted the show to have more of a sketch-comedy energy, and he and O’Brien shared a love of musty show-business con­ventions, which they updated to surreal, hilarious effect. And so one of the most forward-looking comedy shows on televi­sion featured a profane hand puppet (Tri­umph the Insult Comic Dog), a tribute to the Sixties animated series Clutch Cargo (in which moving lips were superimposed onto still photographs of people like Bill Clinton, who, as voiced by Smigel, became a hooting hillbilly), recurring characters (the Masturbating Bear! The Coked-Up Werewolf! Tomorry the Ostrich!) and a giant lever straight out of the era of live children’s television (only in this case, pulling the lever triggered random clips from Walker, Texas Rang­er). In the very first episode, O’Brien also passive-aggressively debuted “Actual Items,” a much funnier parody of Leno’s signature wacky-newspaper-headlines bit.

It’s unclear if NBC will be fighting O’Brien for intellectual-property lights on certain bits and characters created on the old show. “If there’s something we did for a long time that we’ve established as ours, we’ll figure out a way to do it,” O’Brien says. “I won’t be denied my Mastur­bating Bear! What I really wanna do is be sued over the bear and then appear in court with the Masturbating Bear. ‘Your Honor, this bear can’t help himself!'”

O’Brien’s humor is so re­lentlessly self-deprecating, it’s easy to overlook the fact that he also has a serious ego. He comes from a family of overachievers: the third of six children, father a prominent microbiologist, mother a prominent lawyer. Unlike, say, Letterman, whose comedy seems to come from a place of deep self-loathing, O’Brien acknowledges that underneath “layers of questioning, doubting, double-checking, worrying,” he possesses a “solid adamantium core of confidence.” He knows he’s generally the funniest guy in the room.

Which isn’t to say that he lacks a work ethic (once described by O’Brien himself as “almost humorless”) that borders on the obsessive. “I was very whatever adjective you come up with for the opposite of laid-back,” acknowledges O’Brien. “My natu­ral tendency is to overthink, often to my detriment.” He has been in therapy for de­pression, and despite a tendency, in Smigel’s words, to “never want the audience to feel like he’s not their friend,” a darker streak will occasionally emerge from that goofy, crowd-pleasing exterior. The cold opening of O’Brien’s very first episode of Late Night ended with him preparing to hang him­self. “On Saturday Night Live, Conan and I got along right away because we had this work ethic in common, and we both have a melancholy side,” says Smigel. “We would go out to dinner a lot, but we wouldn’t enjoy ourselves.”

Working 12- to 16-hour days, O’Brien eventually became more comfortable in front of the camera, and the audience got used to the odd rhythm of his perfor­mance style.

“I look at other people – Letterman’s a perfect example – and I think, ‘Oh, he’s a precision instrument,'” O’Brien says. “And I mean that as a high compliment. But my­self, I’m not a precision instrument. I go out there and I try stuff and I move and I do things, and when I hit a rich vein, I jump into it and really go for it. And I let people in on my vulnerability. People know when something isn’t going well, or if there’s an awkward moment, and when I get excited and happy I move around a lot. There’s that famous Marshall McLuhan quote where he said, ‘Television’s a cool medium.’ And I always thought, ‘If televi­sion’s a cool medium, I’m fucked.’

“But,” O’Brien continues, “as badly as things went in the beginning – and this sounds weird – but I always wanted to be there more than anybody didn’t want me to be there. You know what I mean? I’m very aware when I’m not right for something. So let’s say I had somehow been made the quarterback for the New England Patriots, replacing Tom Brady. I would ask to be taken out of the game after my first hit. But no matter how hard I got hit on late-night television, I never want­ed to be taken out.”

After taking over as host of The Tonight Show, O’Brien began having troubles right from the start, as he simultaneously attempted to make a play for Leno’s older-skewing, more conventional audience while stay­ing true to his fans with weirder bits like the unsubtitled, all-Spanish Telemundo satire “Conando.” He ended up not entire­ly pleasing either demographic, and the show began regularly losing to Letterman in the ratings for the first time in more than a decade. “I think I started out being very cautious about taking good care of this amazing franchise,” O’Brien acknowl­edges. “I would think, ‘Is this a good To­night Show bit?'”

In the end, with the ratings for Leno’s prime-time show cratering and local affiliates demanding stronger lead-ins for their lucrative evening-news programs, O’Brien’s fate was sealed. “As a producer, you’re talking to all of the finance and sales guys, and everything on our end meeting all projections,” insists Jeff Ross, O’Brien’s longtime producer. “That was not the problem. The Leno disaster was the problem. And then it became, ‘Who’s cheaper to get rid of?'”

O’Brien prefers not to say much about the end of his Tonight Show, referring only obliquely to “the events of the last nine months.” He certainly emerged as the classiest actor in the affair, person­ally writing a heartfelt final message to his audience (in which he even thanked NBC) and paying additional severance to his staff out of his own pocket. (With the exception of bandleader Max Weinberg, O’Brien managed to retain his entire staff to work on Conan.) But an interview he gave to 60 Minutes in May came off as self-pitying to some. “Time and again he talked about his departure in the agonized terms of someone suffering a fatal illness,” noted The Hollywood Reporter. “Displaying zero of the antic charm that makes him such a great comic in late night…[O’Brien is] be­coming the very person he usually mocks, just another egocentric Hollywood type.” In a headline, Gawker advised, IT’S TIME FOR CONAN TO MOVE ON.

“Knowing what I know, I’m quite con­fident that what happened really didn’t have much at all to do with what I was doing,” O’Brien says carefully. “That’s not to say that my show was perfect. There were things that we did that I really liked and there were things that we did that I thought, ‘Ehhh.’ But given the situation, I don’t think, even if I had done a radically different show, anything would have been different. I honestly believe that. And I’m fairly hard on myself.

“In some ways, I planned and worked for five years toward this one thing that was supposedly the epitome of my tele­vision dreams,” O’Brien continues. “And then the still-kind-of-unthinkable hap­pened. But one of the advantages of that experience is to really feel like, ‘OK, I’m going to go for broke. I have got nothing to lose.’ Let’s face it: I’m not going to do an­other television show after this one.”

When O’Brien moved his family to Los Angeles for The Tonight Show, they bought a five-bedroom colonial home in Brentwood. It’s white and columned and un-flashily decorated, like a tasteful suburban New England residence airlifted into one of the most exclusive neighborhoods in Southern California. One afternoon, in his bright, airy kitchen, O’Brien pours me a Sierra Nevada into a pint glass and, less happily, pours himself a glass of water. To get into the spirit of California living, he’s been on what he calls a “very L.A.” diet that bans, among other things, sugar, caffeine and alcohol. His wife, who has just arrived, and who is petite and blond, asks if he’d like some hummus, a snack not forbidden by the diet. “No, I’m good,” O’Brien says, turning to me and adding, “She’s on the same diet. We’re both ready to kill somebody.”

We move into O’Brien’s home office, a dark-paneled den decorated with photo­graphs of his family, an original I’M WITH COCO poster, framed architectural render­ings of the set of The Tonight Show and a punching bag covered by his writing staff with the phrases most commonly heard in sketch meetings (i.e., “No, Conan, the joke makes fun of racists – the audience will get it!”). There’s also a rack of guitars, in­cluding an exact replica of the Epiphone Casino John Lennon played on Let It Be, down to the nicks and scratches and re­placement knobs. “Backstage at the show, I thought it would be cool to show this one to Elvis Costello,” O’Brien says. “But he just shook his head and said, That’s sick,’ and walked away.”

On another wall, there’s a framed note from Jack Paar, the second host of The Tonight Show, predicting O’Brien will “some­day get the Paar-Carson talk-show slot.” “It’s like, ‘Hmm, didn’t he leave a name out?'” O’Brien says.

This is the only mild moment of criti­cism of Leno that O’Brien allows himself. When I ask if he felt gratified by the sav­aging Leno received at the hands of other comics, O’Brien says, “I think this was an­other instance where NBC chalked it all up to me. If you look at the tapes, I probably made three jokes about him. Which I think I was entitled to do. But I was very careful not to go to town.”

We settle into leather chairs on either side of a stone-topped coffee table. There are books everywhere: Roberto Bolano’s The Savage Detectives, the collected poems of John Berryman, collections of Chekhov, Barry Hannah, George Saunders, Lorrie Moore. O’Brien’s wife, who has an MFA in creative writing, is always trying to turn him on to fiction, but O’Brien most­ly reads history – most recently, a biogra­phy of Mark Twain and a book paralleling the capture of Jefferson Davis with Abra­ham Lincoln’s funeral. O’Brien calls Lin­coln “my ultimate human being,” insist­ing, “Most people that you read about in history, the more you study them, the less impressive they become. Lincoln is one of the only ones where the more you find out, the more impressive he is. He was also our funniest president by far.”

O’Brien’s seven-year-old daughter, Neve, enters the room with her hands on her hips and asks, “Where’s Mommy?”

“Oh, Mommy?” O’Brien says. “She went to China, I believe.”

“Daddy!” Neve shouts, mock-exasper­ated. Theatrically stomping her foot, she marches out of the room.

O’Brien turns to me and says, “She’s like a sitcom kid. I scream at them at night, ‘You’ll have a good blow [sitcom jargon for a joke funny enough to end a scene] and then out!'”

The final episode of O’Brien’s Tonight Show ended with a raucous, valedictory cover of “Freebird,” featuring Beck, Billy Gibbons of ZZ Top, Ben Harper, Will Ferrell on cowbell (and handling the apt lyrics) and O’Brien on guitar. “It was sort of like an Irish wake,” O’Brien says. Since part of his $32 million settlement with NBC in­cluded a noncompeting clause forbidding him from performing on television or radio before September, O’Brien began thinking about putting together a band and play­ing a few low-key club shows, “in an Andy Kaufman kind of way, wearing a silly cow­boy outfit, where people would eventually figure out it was me.” But one of O’Brien’s agents at the touring arm of William Mor­ris got wind of the idea. “They fed my name into a computer, like, ‘Conan does a show,’ and apparently whipped cream came out, or the computer blew up,” O’Brien says. “My producer told me, ‘There’s a really strong interest in this.”

The shows featured different guests at each stop, everyone from Vampire Week­end to Jim Carrey. O’Brien discussed his eight-step recovery process (which includ­ed Blame Everyone Else, Blame Yourself, and 36 Hours of Red Bull and Halo), covered Radiohead’s “Creep” in the voice of the chimney sweep from Mary Poppins, wore the purple leather suit from Eddie Murphy’s Raw and inflated a giant bat purportedly from Meat Loaf’s Bat Out of Hell tour. (Though, actually, O’Brien admits, it was a knockoff: “We asked Meat Loaf if we could use his bat, and he suddenly got all squirrelly and said, ‘I don’t know.’ Then he said, ‘I’m busy. I’m using it.’ And then we checked out his tour schedule, and he wasn’t! Like, what are you using it as – a bouncy castle at a kid’s party?”)

O’Brien found the shows exhilarating and therapeutic. “The best experience I’ve had in show business in my entire life was that tour,” he says. “My whole career has been an attempt to get close to that red-hot core of real show business. That’s what I loved about Saturday Night Live, and then the Late Night show: I’m back­stage, people are running around, there’s cameramen, people in horse costumes. But this tour was the final extension of that, where I’m putting on my own make­up in some dingy dressing room, with the old lights around me, and the band’s playing the warm-up. You know, I went back in time. I was in vaudeville.”

As the debut of Conan nears, the man­tra of Team O’Brien remains clear: Con­tinue to harness that vibrant, ineffable quality that made the final weeks of The Tonight Show and the subsequent live tour so thrilling to watch. The problem, of course, is that part of what made those performances so special was their rarity. It’s not every day that you get to see a major star spend a week mocking his employer after he’s been shafted, or see that same star perform a relatively intimate show in your hometown with all sorts of surprise guests. The tour dates were unique, un-reproducible moments, desirable precise­ly because you couldn’t conjure them on-demand on the screen in your pocket.

Add to that the problem of standing out in the increasingly clotted modern-media landscape. When O’Brien debuted on Late Night in 1993, he faced no talk-show competition whatsoever for two years in his time slot. (And after that, the com­petition was Tom Snyder.) Today, at any given moment, you can watch new con- tent from Letterman, Leno, Kimmel, Craig Ferguson, Jimmy Fallon, Bill Maher, Jon Stewart, Stephen Colbert, Chelsea Han­dler, George Lopez, Saturday Night Live, Between Two Ferns With Zach Galifianakis and, via YouTube, pretty much any clip filmed by any comic ever in history. “All of the ratings are a disaster now,” admits Ross. “Leno’s doing worse than we were doing a year ago. Letterman’s doing terri­bly. A lot of it has to do with the fact that there’s too much out there.”

O’Brien worries about all of these fac­tors, in part because he is a congenital worrier. “I remember, he would always say, years ago, ‘Is everything going to work out with my career?'” Powel tells me. “And it would be like, ‘What are you talking about? You’ve had the Late Night show for 10 years already!” To capture the energy of the live shows, he’s considering blend­ing more music into Conan, as well as in­corporating more interactive, online ele­ments, though what exactly that means is vague. O’Brien says he’s on his computer all the time, but that he’s basically “looking up weird facts about Bess Truman,” and ac­knowledges that when someone first sug­gested he begin Twittering, his response was, “I’m the person who makes fun of ce­lebrities on Twitter.”

(And, in fact, his daily tweets have felt somewhat lackluster, like concoctions of a street-team marketing department.) “With the new technology, what we’re losing track of a little bit in en­tertainment is mystery,” O’Brien says. “The big trick is to let the fans in, but also still surprise them. That’s the tightrope act of the modern era. Everybody wants to shoot a behind-the-scenes. And then somebody else wants to shoot a behind-the-scenes of the behind-the-scenes. Every day, my Web people come to me and say, ‘We want to show…’ If they could, they would re­lease my first show online 48 hours before it aired. They don’t understand when you tell them, ‘Yeah, but who would tune in to my show?’ ‘But it’s so cool! It’s going to go viral! We’ll get so many hits!'”

As for specifics, O’Brien and his writers are mulling the idea of titling each night’s show like an old crime series from the Sev­enties (“And tonight’s episode…’A Time to Kill'”), or having a big seven-month-anniversary special when they surpass the number of episodes they did for The Tonight Show. But O’Brien knows his greatest strength as a comic performer is reactive, improvisatory, and so can never entirely be preplanned. “The really great moments that have happened to me over the years in late-night television have al­ways been a mistake,” O’Brien says. “Some­thing happening in the moment, where things go off the rails, but it’s beautiful.”

In a sense, it’s suggested, the past nine months have been an epic version of just such a moment, with O’Brien, in free fall, forced to take his improv game to a whole new level.

“Yeah, exactly,” O’Brien says. “The most classic moments in late-night television, like with Carson, when Ted Ames throws the tomahawk at him and almost hits him in the crotch? Those were mistakes. And you are right. I hadn’t thought about it that way, but the last nine months has been one giant tomahawk in the crotch. But it has been fascinating.

“There are times when I’ve told myself, ‘Maybe I could have gone on and done The Tonight Show for 15 years, but never had the impact that I had doing those last six shows’ – so maybe that moment’s a gift, you know?” O’Brien continues, sound­ing as if he’s still trying to convince him­ self. “The crazy thing about this business, the thing that keeps you going, is you’re al­ ways greedy. You can get into a funk, and beat up on yourself. Because you’re always thinking, ‘Maybe I can get one more mo­ment like that out of my career.’ And you’ll walk across glass to get it.” He means “broken glass,” of course. But for a mo­ment, it’s hard not to picture O’Brien, like some silent-film clown, gingerly stepping onto an endless glass surface, smooth as ice, where the possibilities for a flawless pratfall are infinite. 

In This Article: Conan O'Brien, Coverwall


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