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Conan on the Couch

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The third of six kids—his father is a microbiologist and his mother a retired lawyer, and despite such professions, they are apparently very funny—O’Brien discovered late-night television at 10, when his dad, who never missed a night of Johnny, let him stay up for the monologue on Friday nights. “I was interested in this guy who made my dad laugh,” says O’Brien. “I remember watching Carson the day after Don Rickles hosted for a week. He noticed his pencil box was broken. McMahon said it was broken when Rickles was there. Carson walked off the set to where Rickles was filming C.P.O. Sharkey. I think my eyes melted: ‘He can walk off one show and go onto another show?!’ ” Shortly thereafter, “I was one of these kids who really paid attention to what was happening on TV—‘Alan Thicke is going to have a show? Let me check it out and see if it’s going to be any good.’ ”

“Apparently, there’s a new Paris Hilton sex video. Hilton said, ‘I feel the first one left a lot of unanswered questions.’ ”

O’Brien’s other comedic touchstones are Saturday-morning Warner Bros. cartoons (he loved the coyote and how all those jokes had to work silently); an SCTV skit in which John Candy, as Yellowbelly, a cavalry officer kicked out of the Army for cowardice, shoots a mother and child for saying his name; the Eiffel Tower–is–in–D.C. episode of Green Acres; the Batman episode where the villain Shame insults Batman with the line, “Your mother wore Army boots,” and Batman responds, “Yes, she did, and she found them quite comfortable.”

“Anything ridiculous and apropos of nothing, I responded to,” says O’Brien. He was 16 and leaving for school when his sister called him back inside the house to see David Letterman on his morning show. “He had a photo of a dog behind him and a gap in his teeth and he looked completely strange,” says O’Brien. “At that moment I realized things were going to be different.”

As a college sophomore, O’Brien made a pilgrimage to Rockefeller Center to see Letterman. Now he works in the same studio and wishes he could stay. But Rock Center forever may turn out to be a pipe dream for O’Brien—Letterman, whose contract is up in 2007, might end up staying longer than Leno, just to win the last battle of the late-night war. If Letterman’s still kicking around, O’Brien will most certainly need to take his show to Burbank (NBC moved Last Call With Carson Daly, the show that follows O’Brien’s, to Burbank this summer). “Well, there’s a lot of television history in Burbank,” says O’Brien, over dinner at Lattanzi, an Italian Jewish joint in midtown apparently popular with the ranks of the comedy elite—Lorne Michaels is in the back “Lorne’s Here Room” with new Saturday Night Live cast members, and everybody meets awkwardly on the stairs of the restaurant. The new kids tell O’Brien they love the way he reinvented late night. “Why did you say that with a question mark?” drones O’Brien.

He settles in his seat. “I’m open to going to L.A.,” he says. “Mostly because it won’t be my choice.”

In many ways, O’Brien is unscarred by his celebrity. I asked him if he enjoyed himself at the Emmys two weeks ago: “I like the presenting, but I don’t like the sitting,” he says. “I really liked hanging out with Will Arnett and Sacha Baron Cohen—being with people like that is why I got into this business. Will and I walked into the Governor’s Ball, and we were just acting like asses. I kept explaining to him that a lot of people were going to be asking me for my autograph, and he was saying, ‘That’s terrific, Conan. I’m going to use this candlestick to rip my throat open now.’ It was stuff you’d be doing to amuse your friends if you were 8. I love that.”

“Donald Trump said if he were president, he would’ve caught Osama a long time ago. Then somebody explained to him that Osama and Omarosa are not the same person.”

He’s a Harvard boy, and not everyone likes those. O’Brien, two-time editor of the Harvard Lampoon, an honor shared with Robert Benchley in 1912, doesn’t make fun of himself all the time. He spends an enormous amount of time explicating jokes, and there is nothing funny about that. (He should perhaps heed Michaels’s advice: “I don’t want to get into any theoretical ideas about comedy,” Michaels says to me. “Anybody who talks about comedy for more than two minutes is not funny.”)

O’Brien does have some sharp edges, mostly stemming from his differentiation between dumb people and smart people—he sneers at the writers from time to time and calls out to his assistant in a tone of voice that gave me chills (he makes free use of a button he can press on his desk to slam his door shut, too). Oh, the villainy! And he goes on and on about his own work ethic and has little respect for guests he deems not worthy of his show—his highest praise is calling them “likable.”


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