Over the last few decades, the Leno-Letterman dialectic has grown from a humdrum tussle over ratings into one of our all-time great pop-cultural binaries, right up there with Lennon-McCartney, Zeppelin-Floyd, and Faulkner-Hemingway. It’s more than a clash of styles—it’s a deep existential rift, a fracture running the length of America’s funny bone. The differences are obvious and visceral. Letterman is the sour, gap-toothed renegade devoted to absurdist conceptual comedy—non sequiturs, impromptu Dada street theater, suffocating irony. Leno is the bland, slab-faced, corporate-friendly panderer with the comedic temperament of an eighth-grade boy circa 1989: Blondes are dumb, gay men are silly, and Michael Jackson is hilarious in every single context the human mind could ever hope to imagine. To anyone with even minimal comedy standards—those who don’t, e.g., hyperventilate over the riddles printed on Popsicle sticks (a Jelly-copter!)—Leno’s long-standing dominance of the ratings must rank as one of the world’s inexplicable cultural tragedies. The last moment of late-night sanity came way back in 1993, when Letterman, having been denied his rightful place as heir to Johnny Carson’s Tonight Show, decided to thrash his usurper by defecting to CBS, where his victory was both instant and total, critical and popular. It was also short-lived. Within a couple of years (critics usually finger, as the tipping point, Hugh Grant’s 1995 apology on the Tonight Show for soliciting a prostitute), Leno owned every major demographic.
One of the great promises of the writers’ strike was that it would correct this injustice. The strike knocked both hosts off the air for two months, and they returned on opposite sides of the karmic fence. Letterman had worked out a separate peace with the strikers, so he came back with a full writing staff, all-you-can-eat access to a buffet of suddenly underexposed A-list guests, a fetching gray beard, and the moral high ground. Leno, meanwhile, hobbled back onstage with his comedic kneecaps broken: starved of picket-conscious Hollywood stars, forced to write his own monologues, and if not exactly a scab, then at least a slightly discolored skein of flesh growing over the surface of an open wound. Letterman got Denzel, Stallone, and Katherine Heigl; Leno had Bill Maher, the judges from Dancing With the Stars (opening line of interview: “I don’t know anything about you”), and a comedian discovered five years ago on Star Search. Everything was in place for Letterman to reclaim his stolen throne.
Except, as it turns out, none of that mattered. Leno won, despite the handicaps, as handily as he always has, by more than a million viewers a night. This raises a series of difficult questions. How has the prince of pandering attained such a chokehold on the American viewer? What dark magic does he wield? After all these years, is it time for comedy snobs to accept that Leno’s reign is not a fluke—that his combination of skills and style is, in some baffling but real way, better than Letterman’s?
To find out, I watched, more closely than I ever wanted to, a recent week of strike-era Leno. Some of his jokes were so bad they made me flinch like I’d just downed a strong shot of liquor (“It was so windy, on Hollywood Boulevard I saw a guy take the chain out of his nostril and tie it to a lamppost just to keep from blowing away”); others made me shake my head gravely like you do when you see someone mistreating a pet (people thought Huckabee’s admission that he ate fried squirrel in college would hurt him in the polls, “but in South Carolina he went up 30 points!”). Leno didn’t seem to mind, though: He just put his hands in his pockets, waggled his head, chuckled to the band—and immediately told another joke. One night, Bill Maher called Leno “virtually the only person I know … who could write an entire monologue by himself”—which sounded ridiculously overblown at the time, but on further reflection might actually be true.
By all accounts, Leno works on monologues obsessively—seven days a week, in the middle of the night, in comedy clubs, and on his days off. More than any other comic, he has devoted his life to that opening blitz of rapid-fire topical groaners. It’s his signature achievement. The Leno monologue is always impressively long and covers lots of ground. On a recent night, before he sat down at his desk, he told jokes about 24 different subjects, from botany to Britney to the production of Japanese electricity. Letterman covered only five.
Pundits who thought the strike would cripple Leno misunderstood something fundamental about his art: His act is already essentially crippled. Real stand-up comedy is famously time-intensive; it converts months of solid work into minutes of material, and its tiniest successes depend on superhumanly precise calibrations of tone, pace, and gesture—a discipline antithetical to the relentless, workaday schedule of a talk show. A monologue is, by definition, wounded comedy. We should assess late-night hosts, then, not by their rare bursts of excellence but by how they cope with mediocrity. Leno and Letterman both, at this point, deal mainly in terrible jokes. The question for viewers is what attitude—what existential garnish—do you want on top of them?
Letterman seems to loathe his monologue. He performs it grumpily, as a duty, and most of the humor comes out of his apparent disdain for the jokes, half of which seem to send him into acute liver failure—he squints, grimaces, chokes back vomit, very nearly dies. This irony insulates him from the material: He didn’t write the jokes, he wants us to understand, and he’s not really behind them, he’s just the one stuck up there reading them. He’s a failed idealist; it can be painful, night after night, to watch him betray his own high standards.
Leno, on the other hand, is a realist. He doesn’t pretend to be better than his material or his audience. He’s a virtuoso of the mediocre, resigned to the staggering failure rate of late-night comedy and proud of whatever success he manages to bring off. Unlike Letterman, he tells his jokes straight, with the implication that they are actually funny and worthwhile. His only protective mechanism is his legendary work ethic: Since striving for quality in a late-night monologue is hopeless, he invests all his talent in quantity. This is the secret of Leno’s success: He’s not trying to be the funniest guy in the world; he’s trying to be the most dependably serviceable at monologuing—an equally difficult task that carries almost none of the turkey-cocking street cred of revolutionary art comedy. Like many Americans, Jay Leno works as hard as he can under impossible conditions (he even knows he’s losing his job next year), and he refuses to beat himself up for it—a position that is, in the end, riskier, more vulnerable, and easier to identify with than that of his nearest rival. And, if you can manage to think about it without irony, very nearly heroic.