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Letterman, typically, managed to turn the comedian's predicament itself into the joke. For months after Obama's Inauguration, the Late Show host trotted out a nerdy staff writer to read his latest attempts at coming up with Obama jokes — all of which turned out to be lamely repurposed Bush jokes. ("Barack Obama is so dumb, when he was governor of Texas, someone asked him what the capital of Texas is, and he said, 'Capital T.' ") Still, the edge that crept into Letterman's comedy during the Bush years has, if anything, only gotten sharper. (Yes, he was forced to apologize for a joke about Palin's daughter, but his obvious distaste for the former Alaska governor is evident in the wisecracks that have continued ever since.) In fact, Letterman's monologues have doubled in length — from eight jokes a night to 16 or more — in the past year. "Sure, we'd love to see Obama trip on an Oriental rug," says Letterman writer Bill Scheft. "But there's plenty there. Have you seen those town-hall meetings?"
Jon Stewart's Daily Show too has seemed even more energized in the Obama era. Stewart's great discovery, of course, was that political satire in the 2000s no longer requires actual jokes. All that's needed is merely to present the hypocrisy and pomposity of political leaders in their raw, unvarnished form (Republicans denouncing Sonia Sotomayor on the floor of the U.S. Senate, say, before her inevitable confirmation) and append it with a sarcastic exclamation point or simply a mugging reaction shot. And if conservative politicians and talk-show hosts still bear the brunt of most of Stewart's barbs, Obama has hardly come away unscathed — from Stewart's early lampooning of Obama worship (in one video, the Democratic candidate was presented to the world like the royal cub in The Lion King) to his impatience with the friendly interplay between Obama and audience members at his first health-care town-hall meeting: "Is this a town hall or a Tom Jones concert?"
Indeed, the Obama era has helped clarify an often overlooked dichotomy in late-night TV comedy: the divide between the political satirists (Stewart, Stephen Colbert, Letterman much of the time) and the topical jokesters (Leno, Conan O'Brien and Jimmy Fallon). O'Brien's middle-of-the-road, Carsonesque wisecracks in particular ("President Obama's approval ratings have slumped to an all-time low, which explains Obama's new Secret Service code name: NBC") are looking comparatively tame now that he's opposite the increasingly politicized Letterman — whose contempt for Bush-era politics comes through in his interviews as much as his gag lines. (It may not be a coincidence that Letterman is beating O'Brien in the ratings.) Letterman may have wimped out in apologizing for his Palin joke, but it's hard to imagine O'Brien even cracking a Palin joke worth apologizing for.
The Bush presidency, it turns out, may have had a more lasting impact than comedians appreciate. As it opened up a bitter divide in the country, it forced stand-up comedians to take notice — and take sides. Even with a President who's no longer a ready-made joke, for comedians, there's no going back. As for Obama, he'll need to watch his step. Those White House rugs can be dangerous.