The Left sees Bill Maher as a sell-out, the Right sees him as a useful idiot, and Donald Trump sees him as a last resort. Maher’s arc mirrors that of the Baby Boomers more broadly, who struggled to find their identities after becoming part of the system they once resisted.

On Thursday, Maher confirmed he would accept the Kennedy Center’s annual Mark Twain Prize for American Humor in June, making him the last comedian to be awarded before Trump closes the center down for two years. Beset by anti-Trump artist boycotts, the prestigious venue stumbled after the President returned to 1600 Pennsylvania Avenue and is now closing for renovations — almost certainly to sidestep further fallout.

Under ordinary circumstances, a Twain Prize would be worth crawling through glass for most comedians. But these are not ordinary times. Most A-list comics are unlikely to cross a picket line to be celebrated at the newly renamed “Trump-Kennedy Center”. Maher, however, is not most comedians.

The Real Time host is more than two decades into a run at HBO, where he decamped after ABC canceled Politically Incorrect in 2002, not long after Maher caused the network major controversy. “We have been the cowards lobbing cruise missiles from 2,000 miles away,” he said after the 9/11 attacks. “That’s cowardly.” Corporate advertisers revolted and, less than a year later, the show ended.

The proto-woke movement that reared its head in the Nineties allowed Maher to position himself as something of a bad boy at the time — at least to the extent that a broadcast network would allow. His schtick became saying the unsayable, which in the 2000s most often took the form of smugly chastising the Bush-era Right. And that was typically in front of a studio audience comprising California liberals on a show run by California liberals. Evangelical Christians and Dick Cheney were easy targets.

As the Trump era dawned, Maher gradually started to shift his focus. Most comedians were part of the hysterical overreaction to the President, leaving a lot of low-hanging fruit for jesters such as Maher, Dave Chappelle, and Shane Gillis. But it was an uneasy alliance. Maher, who now also hosts the bizarre, smoke-filled Club Random podcast, reveled in the backlash from his fellow liberals — maybe too much. The Right began latching onto his friendly fire, using clips and running headlines so frequently that it became a regular occurrence for some conservatives to urge their fellow Rightists to stop embracing him.

A large part of Maher’s audience is affluent Boomer centrists who can afford HBO and are tired of both parties. Indeed, just this year Gallup found a record number of Americans now identify as political independents, including one third of Baby Boomers. That means his audience has grown up with him. The trouble, though, is what happens when you hate the man so much you become the man?

Like many Baby Boomers raised in the heyday of the American Century, as the country climbed out of Watergate and Vietnam, Maher still sees himself as a rebel, even as he’s settled into a comfortable career. It’s what makes him the perfect Trump-era recipient of the Mark Twain Prize.

But is Trump a rebel? Now in his second term, with a soaring net worth and Silicon Valley at his beck and call, that’s harder to argue. Maher’s acceptance of the prize places him in the position he has occupied since hosting Politically Incorrect on a major broadcast network: navigating a culture that feels alternately woke, fascist, or perpetually both.

Maher, like many Americans, has no coherent identity in this climate.

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Emily Jashinsky is UnHerd‘s Washington correspondent.

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