The Real Problem With Jon Stewart

It wasn’t too many years ago that Jon Stewart was the king of political comedy. When he hosted The Daily Show, his monologues were water-cooler talk for a generation of urban sophisticates.

“Before he retired from Comedy Central, The Daily Show was one of the most-watched shows on TV,” recalled Nellie Bowles of the New York Times on a recent podcast episode. “This guy was amazing. I remember I watched it every night; I loved it.”

Even though he could sometimes be an equal-opportunity offender and make digs at the left, his milieu was making fun of the right. But the thing was, even when he was making conservatives angry, he could be funny.

Stewart quit The Daily Show right before the Trump era, which means he missed out on a golden opportunity for his brand of comedy. Post-Stewart, left-wing late-night comedy these days is unfunny and full of cheap shots and low blows aimed at conservatives. Lesser comedic commentators like Stephen Colbert, Seth Meyers, Trevor Noah, and John Oliver are insufferable, and they don’t even have occasional moments of genuine humor. Saturday Night Live goes woke and unfunny more often than not these days too.

Stewart has become one of those lesser comedians too, or at least that’s what his post-Daily Show career seems to suggest these days. His new show on Apple TV+, The Problem With Jon Stewart, garners a fraction of the viewers that The Daily Show did under his watch. To be fair, a streaming service is bound to bring smaller numbers, and the sparse, bare-bones production of the new show isn’t winning over critics or fans.

But the controversy he generated for his critical-race-baiting of Andrew Sullivan on the eighth episode of the show may be more representative of the real problem with Jon Stewart. It turns out that Trump may have broken Stewart as much as he broke others on the left.

Related: The DOT’s Twitter Meme Doesn’t Just Offend Comedy — It May Also Be Illegal

“The Trump era seemed to have rocked his faith in his former profession,” writes Devin Gordon about Stewart at The Atlantic. “He used to believe in the power of comedy to hold politicians and billionaires to account, and in his own power to at least make a dent. But he’s not so sure anymore.”

Another staff writer at The Atlantic lumps Stewart in with the cheap-shot comic pundits.

My theory of Jon Stewart: in the Daily Show era his core audience tolerated making fun of the left sometimes so long as he mostly made fun of Bush and Fox News, but now, to be liked by folks he wants-needs?-to like him requires unfunny ideological solidarity. See also Colbert.

— Conor Friedersdorf (@conor64) April 22, 2022

The problem with The Problem With Jon Stewart may be generational as well, as Stephen Miller points out at Spectator World.

“Stewart’s show has failed to catch on after seven months, attracting only about 180,000 viewers for its premiere,” Miller writes. “No one is watching, and more importantly, the media at large, which now skews younger, thinks of Stewart as an out-of-touch Boomer.”

Miller later notes that Stewart’s attempt to attach himself to the white-guilt zeitgeist backfired.

“Stewart, of course, tried to adjust to the new culture of wokeness with an episode titled ‘Race’ and a segment called ‘The Problem with White People,'” he writes. “It involved a struggle session with guest Andrew Sullivan and came off like some Upper East Side rich white liberal book club anguishing over Robin DiAngelo. Stewart’s problem is that all this could have been funny, but he chose instead to play the scold.”

Canadian journalist Tara Henley hit the nail on the head in her newsletter this weekend, which actually inspired me to write this article.

“Stewart is an elite liberal. Elite liberals these days are woke,” she summarizes. “And, as many before me have observed, wokeness has a tendency to implode things — institutions, careers, shows, ratings. And, critically, senses of humour.”

Last year, Donald Trump famously said that “everything woke turns to s**t.” Maybe that’s what happened to Jon Stewart’s career. It’s a shame because even when his point of view infuriated me, I still used to find him funny. Now he’s just another wokescold.