Finally. We won something. While everything else in the country—and by everything, I mean, obviously, politics—is being ceded to the all-powerful Middle America, humor is now officially ours. When Jay Leno announced last Monday night on the 50th anniversary of the Tonight Show that he would retire when his contract expires in 2009 and hand his job over to Conan O’Brien, he was telling us that New York City has an impending monopoly on funny. Late Night With Conan O’Brien, Late Show With David Letterman, Saturday Night Live, and The Daily Show are all here, which is to say that soon, if an American wants to watch a television show for laughs, he will have no choice but to deal with us.
Technically, both O’Brien and Leno hail from the Boston area, but their humor is pretty much separated by a continent. While Leno has opted for a blandly reassuring style of japery, obviously pandering to the Nielsen masses, O’Brien is steeped in pure Gotham sardonicism; his sense of humor is weird, conceptual, Harvard-educated. Soon (well, soonish), Leno’s mainstream, avuncular warmth will be gone from television, like the sitcom—another dying form dedicated to sunny consolation as amusement. And people in Kansas will be forced to confront sketches like O’Brien’s self-pleasuring bear.
This is all pretty weird for Leno, the lame duck. He is not talking to the press, except for the cozy and not-super-convincing statement he issued on Monday before airtime: “I felt that the timing was right to plan for my successor, and there is no one more qualified than Conan.” The timing? He gave five years’ notice. (“It’s so far in the future I just pray there is a New York and an L.A.,” Late Night writer Andy Blitz replied when I asked if he’d move to Los Angeles in 2009 if O’Brien decides to relocate the show.) Leno went into more detail in a common-man-themed monologue during the 50th-anniversary show. He said he “sat down with the folks at NBC . . . I don’t have a manager or an agent or anything like that,” and they told him, “ ‘We don’t want to lose Conan O’Brien.’ And I said, ‘Okay, what does that mean?’ ” What it probably meant was NBC president Jeff Zucker offering Leno an enormous chunk of change to stay and then leave on a schedule acceptable to O’Brien, who’d made no secret of his intention to leave NBC for an earlier time slot on another network if he wasn’t handed the Tonight Show, but quick. Leno described his incentives as a bit more altruistic: “When I took this show over, there was a lot of animosity between me and Dave and who’s going to get it . . . I don’t want to see all the ﬁghting, and who’s better, and nasty things back and forth in the press. So right now, here it is, Conan! It’s yours! See you in five years, buddy.”
Garry Shandling, Leno’s first guest after that speech, posed the obvious question: “Are you out of your mind?” And the answer is, it’s too soon to tell. Leno may well be getting out just in time—while he is still No. 1 in the ratings—and Zucker may have been smart to bet on Conan. (If O’Brien had left for another network and become Leno’s competition, who knows? A third candidate can really throw off an election.) Shandling, for his part, looked as if he’d recently risen from the crypt, and it was depressing to watch those two dinosaurs of Los Angeles discuss their situation. “I feel old,” said Shandling. “You just can’t wait till they drag you out by the heels,” said Leno. When I asked former Conan writer Demitri Martin how he thought the subversive, youthful comedy of Late Night would play with Leno’s audience, he said, “I think in ﬁve years a lot of Leno’s audience may have died off.” Of course, there’s the possibility that when O’Brien is installed at the Tonight Show, when he’s in the Oval Office of comedy, he may water it down—become preoccupied with reelection. It is also possible that he will move his operation to Hollywood after the transition to gain the proximity-to-the-stars advantage Leno currently enjoys over Letterman. Who knows? Perhaps his friendliness and authenticity will become so much shtick—and then who will the joke be on? “I’m very happy for Conan, as I imagine he’ll be doing the Tonight Show from L.A.,” says his former sidekick, Andy Richter, “and I know for a fact that it’s been his dream since childhood to one day become the biggest asshole in Hollywood. Mazel to him.”