Why Jon Stewart is flopping

His new show missed the bus — now he’s just an out-of-touch boomer

jon stewart
Jon Stewart on his Apple TV+ show (YouTube screenshot)
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Jon Stewart made one of the biggest career follies in the history of infotainment when he walked away from the Daily Show in 2015, removing himself from the Donald Trump presidency. It’s a mistake from which he’s never recovered.

The Daily Show itself became irrelevant almost immediately thanks to a then-unknown replacement host (Trevor Noah), while just about every late-night comic adopted Stewart’s model of faking the news (Late Night with Seth Meyers, the Colbert Report, Last Week Tonight with John Oliver, Jimmy Kimmel Live! and a dozen others).

Stewart has now managed to destroy the credibility…

Jon Stewart made one of the biggest career follies in the history of infotainment when he walked away from the Daily Show in 2015, removing himself from the Donald Trump presidency. It’s a mistake from which he’s never recovered.

The Daily Show itself became irrelevant almost immediately thanks to a then-unknown replacement host (Trevor Noah), while just about every late-night comic adopted Stewart’s model of faking the news (Late Night with Seth Meyers, the Colbert Report, Last Week Tonight with John Oliver, Jimmy Kimmel Live! and a dozen others).

Stewart has now managed to destroy the credibility of two industries, journalism and comedy, without ever looking back. Journalists admired Stewart because he was the class clown who could say things about Republicans they all wanted to but couldn’t because of something known back then as media ethics. News websites created a cottage industry of “Jon Stewart destroys…” and “Jon Stewart obliterates…” headlines with stories that consisted of nothing except his embedded clips. Jon Stewart wanted to be a journalist and all the journalists wanted to be Jon Stewart.

Stewart might have disappeared during the Trump years but he returned last year with a streaming show on Apple TV+, The Problem with Jon Stewart. The real problem, though, is that even to this day, Donald Trump continues to drive the news cycle. The audience has moved on from political partisan whiplash and snappy one-liners to larger, more serious narratives of systemic racism and trans rights. On this, Stewart missed the bus.

As originally reported at Bloomberg, Stewart’s show has failed to catch on after seven months, attracting only about 180,000 viewers for its premiere. No one is watching, and more importantly, the media at large, which now skews younger, thinks of Stewart as an out-of-touch Boomer. They aren’t going to embed his clips if they have to pay for it. Apple TV+ is still a niche service provided by a company with a passionate product fan base, but Apple no longer dominates the market like it used to, either in technology or in cultural influence.

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.” 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.

Moreover, there’s nothing original about Stewart’s newfound white guilt. The audience he’s playing to can get this stuff in the New York Times or on CNN without having to subscribe to a new streaming service. They can also get it on TikTok or Twitter — or just put a black square on their Instagram and, bang, they’ve solved racism.

These are the sorts of things Stewart once lampooned in his own partisan way. But he’s joined the mob now, and the mob is already big enough.

The only recent occasion when Stewart made any kind of residual impact was when he appeared on his old friend Stephen Colbert’s show and seemed to concede the point that the novel coronavirus was leaked from a lab in Wuhan, China — much to the surprise of Colbert. Stewart should have learned a lesson from that: there is real ground to be made in pushing back against mainstream media orthodoxy. Instead he’s become just another voice in a culture and media echo chamber that he himself created and that doesn’t need him anymore.