The following is an excerpt of an article from the Nov. 11 issue of Rolling Stone. This issue is available Wednesday on newsstands and Friday, Oct. 29, online via Rolling Stone's premium subscription plan.
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.
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