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Jon Stewart Drops First Look Trailer for New Apple Show

The Hollywood Reporter logo The Hollywood Reporter 9/21/2021 Lacey Rose

In a matter of weeks, Jon Stewart will be back on your TV.

His new entry, The Problem with Jon Stewart, is set to roll out globally on Apple TV+ beginning Sept. 30. The series, a single-topic public affairs show that’s drawing early comparisons to John Oliver’s Last Week Tonight, will tackle issues, or “problems,” including the struggle for comprehensive veteran care to better ways to support the American working class. And unlike his previous Comedy Central entry, which earned Stewart 22 Emmys and cult-like status among Hollywood liberals, he is hopeful the biweekly offering allows for the kind of deeper dive that he’s after at this stage of his career.


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“I got burnt out on the pace of The Daily Show and also just my inability to evolve it to another satisfying place,” he told THR as part of a September cover story. “I knew that I could play out the string, but that didn’t feel particularly satisfying for me or for the audience, and wouldn’t it be nice to give people a chance to fall in love with the show again in a different way? And then of course get disappointed with it in a different way because that’s the cycle.”

The just-released 30-second teaser for his new series attempts to give viewers a sense for what’s in store, including a glimpse at a lively producers meeting, at least one panel featuring those impacted by the “problem” being explored that episode and two different sit-down interviews, one featuring U.S. Secretary of Veterans Affairs Denis McDonough (set for episode one on vets) and another with U.S. Secretary of the Treasury Janet Yellen (for episode two, on the economy). On-location interviews were formerly the territory of his Daily Show correspondents, though Stewart insists his Problem sit-downs require “a much lower level” of difficulty.

“It’s not what the correspondents had to go through. I’m not plopped into, like, a parade of people against vaccines, and then I just got to fight my way out to the side,” he explained, mere hours after sitting with Yellen in late August. “No, it’s a quite gentlemanly one-on-one. So far, there’s no fisticuffs, and any interview that doesn’t end in fisticuffs has to be considered a positive.”

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