In spite of his rebellious aesthetic, Letterman has always cared deeply about ratings. After all this time, he was just beginning to accept the idea of losing to Leno. “I think more people are responding to Jay than will ever respond to me, and after a while you have to face that,” he told Rolling Stone. “It seems unlikely that now, after years and years of trying under a wide variety of circumstances and advantages and disadvantages, that suddenly I’m going to prevail. You can’t go through life fooling yourself.” It felt, at least, like a gentlemanly loss, tempered by the fact that the cool kids, the comedy snobs, and the showbiz insiders were always going to be on his side. There was something in Letterman’s losing that made him more lovable. Victimhood softened his aggression.
But now—or at least once Conan’s initial curiosity bump passes—Letterman is going to be expected to win again. For the first time since the mid-nineties, he will be the ratings favorite. If he still loses—if the Tonight Show brand turns out to be strong enough to draw more viewers regardless of its host, or if Conan manages to just be flat-out funnier—Dave will have to get used to the idea, all over again, of coming in second. It’s hard to say if going out as the underdog would be horribly depressing or if it might be, in some anti-celebrity, Lettermanesque, renegade way, the most triumphant possible ending to his career: the final affirmation that he stuck to his style at all costs.