For the past sixteen years, Americans have enjoyed the luxury of a perfect comic binary: Letterman versus Leno. Seldom do the cultural stars align so neatly—two ambitious peers, with opposite sensibilities, installed in seats of roughly equivalent power. Their fortunes seemed to seesaw, over the decades, hundreds of times. Early on, Leno was the better stand-up, but Letterman won the favor of Carson. (Leno got himself temporarily exiled from The Tonight Show after a string of mediocre performances.) When Letterman got his own show, Leno became one of his favorite guests. When Carson stepped down, Leno famously sneaked into the master’s chair. Letterman, at CBS, trounced his rival so thoroughly that Leno’s incompetence became a national joke—until, of course, the tables inexplicably turned and Leno ended up flogging Letterman mercilessly in the ratings for the rest of his Tonight Show career. The whole thing felt less like a question of programming than an elaborate social experiment designed to measure, very precisely, some fundamental aspect of the American soul. On one side—Los Angeles, duty, convention, comfort, brightness, professionalism, and the friendly smirk. On the other—New York, rebellion, innovation, elitism, darkness, self-sabotage, and the scowl.
Now we have to adjust to a new binary: Letterman versus Conan. (Leno will take his show to prime time, where he enters into a new binary with a bunch of sausage-grinder franchises like Law & Order and CSI.) On the surface, Letterman-Conan is infinitely less dramatic than Letterman-Leno; the intensities have all dropped out of the equation. They are not peers—when Letterman started his first late-night show, O’Brien was at Harvard studying Faulkner and writing Lettermanesque humor for the Lampoon. There’s no obvious bad blood—Letterman was an early Conan supporter, and, just as Letterman once paid tribute to the retiring Carson (“Thanks for my career”), Conan spent much of his recent Late Night farewell speech gushing over Dave (“David Letterman invented this Late Night show … He set the bar absurdly high for everybody in my generation who does this”). Their stylistic differences will create very few rifts between friends and neighbors. Conan speaks fluently in the late-night language Letterman invented: cerebral non sequiturs; field trips in search of real-world absurdities; forays through the bowels of the studio to interrupt other shows. Both hosts morph into clingy nerds when faced with beautiful actresses. (Conan once screamed like a linebacker and threw his chair after Rebecca Romijn kissed him.) Conan is in many ways a mini-Letterman: tall, lanky, red-haired, stunty, smart. If Letterman-Leno felt like a decades-long slow-motion death match, Letterman-Conan threatens to be its opposite: sweet, cute, possibly even boring.
Really great rivalries, of course, end up nurturing both rivals. Letterman and Leno changed each other’s shticks in all kinds of subtle ways. Dave had to become less abrasive and more committed to his monologue; Leno had to sprinkle a little absurdity over his apple-pie humor and become more human with guests. In a Rolling Stone interview last year, Letterman seemed confused and disappointed that Leno was actually leaving. (“I don’t know why, after the job Jay has done for them, why they would relinquish that.”) All of which raises a fascinating existential question: What does David Letterman mean in the absence of Jay Leno?
The most surprising thing about Letterman, these days, is his familiarity. He’s now the second-longest-running late-night host of all time, which means he’s playing out an impossible paradox: the rebel who won the revolution, the clockwork springer of surprise. We know everything about him. We know his mom, his son, his announcer, his bandleader, his cardiologists, his assistant, and his deli guy. We’ve seen him with and without glasses, with and without a beard. We’ve been with him through national tragedy (9/11), professional tragedy (hosting the Oscars), personal tragedy (his stalker, his quintuple-bypass surgery). He is, in short, as familiar as a cultural icon can get.
The most tantalizing possible outcome of the Letterman-Conan binary is that it will force Letterman, at this late stage in the game, to get better. To stand out against the background of Jay, Dave just had to be Dave. To compete with a younger, hungrier version of himself, he might have to do more than that, for the first time in years. The similarities might turn out to be a blessing: Their stunts will cross-pollinate, their jokes will play against each other. To differentiate themselves, they may even have to launch an arms race of total absurdity.
The most glaring difference between Letterman and Conan is temperament. More than any stunt or recurring skit, Letterman’s signature has always been his attitude: an antisocial aggression that adds real danger to even his silliest jokes. He has a devilish talent for eliciting crazy behavior from guests and then reacting in whatever way will maximize the tension. When Joaquin Phoenix recently went full-bearded weirdo on Dave’s couch, Letterman let the conversation run its slow, uncomfortable course while making it clear that his mighty dignity had been offended (“I’ll come to your house and chew gum”). It’s impossible to imagine Conan, who is polite like Leno, publicly shaming John McCain for blowing off an appearance. Conan is the cartoon version of his angry hero. He wields the Letterman tool kit (the meta-wrenches and irony hammers) to inspire love and affection rather than respect. He wants to disarm people, not put them on notice.
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.