'The Problem With Jon Stewart' Is Stuck in the Past

Jon Stewart’s new Apple TV+ series The Problem With Jon Stewart opens with him meeting with his producers to discuss the topic of their first episode: military veterans enduring severe health problems from their exposure to burn pits — literal trash fires filled with toxic chemicals and other waste that shouldn’t be burned — during their deployment overseas. Head writer Chelsea Devantez recalls that Stewart got the idea from a Daily Show episode where he interviewed 9/11 first responders suffering similar effects from being around the hazardous fumes emanating from Ground Zero.

It is the first, but far from only, time that Stewart and his colleagues will reference his previous TV job. When Stewart goes to interview Dennis McDonough, the Secretary of Veterans Affairs, he observes that he never once on The Daily Show went out into the world to interview someone. Periodically in each episode, a segment will end with Stewart looking at the camera and promising, “We’ll be right back,” even though The Problem runs on a streamer that doesn’t insert commercials, as if it’s a hard habit for him to break even after six years on the sidelines.

That Stewart keeps invoking The Daily Show, both explicitly and with many of his creative choices, will be a feature rather than a bug to those who missed his sardonic voice while he sat out the Trump years as a public voice. But the problem with Jon Stewart is that he hasn’t changed since we last saw him rocking out to Bruce Springsteen in his Daily Show finale, while the world has — both on television and outside of it.

First, there’s the fact that many of his former co-workers now have their own programs covering territory that was once The Daily Show‘s sole domain. Last Week Tonight With John Oliver and Full Frontal With Samantha Bee in particular have spent years perfecting the kind of show The Problem aspires to be: largely devoting each episode to a single issue, with a more serious, at times furious, atmosphere even as the hosts crack jokes.

Stewart’s aware that he’s arriving to a flooded marketplace; in another behind-the-scenes segment, he glances at the writers room white board and quips, “That’s the problem with the comedy-hybrid shows: The whole time we’re talking about this, I’m looking at number one with an asterisk: ‘snake penis.’” And in the early going, he’s struggling to figure out the balance that his old friends have long since mastered. The first episode includes a roundtable of vets who were exposed to burn pits. Their stories — particularly that of one vet who speaks bluntly about how he’s going to die soon and leave his son to grow up without a father — are raw and powerful, but they also leave Stewart palpably adrift in his attempt to mix in even gentle humor. As the roundtable gets darker and darker, he feels the need to remark on the lengthy silence of the studio audience, noting, “I think people are stunned!” (Though even earlier, when he’s doing self-deprecating jokes about how much he’s aged since the mid-2010s, he can’t help commenting on the crowd’s muted response, asking, “I thought you people liked me?”)

The second episode takes on the broader topic of freedom — both the ways it’s in peril around the globe, with the rise of authoritarian governments, and the ways the concept has been invoked by anti-vaxxers and anti-maskers throughout the Covid-19 pandemic. Again, there’s a lot to talk about here — too much, really, to deal with even in a 44-minute episode (or slightly twice the length of The Daily Show once you subtract the ad breaks). In the midst of a roundtable discussion on the state of affairs at home and abroad (featuring, among others, Egyptian comedian Bassem Youssef), Stewart acknowledges how impossible the problems they’re discussing are to untangle, joking, “Everybody wants freedom, and everybody wants to ban shit that they don’t agree with. How do you square that? Good night!” Meanwhile, the rise in anti-democratic voter suppression laws in America is alluded to only in passing, despite being among the most pressing domestic threats to freedom we face right now.

Earlier in the freedom episode, Stewart presents a montage of clips of people talking about how freedom comes with a cost, with members of the Greatest Generation discussing the personal sacrifices they made when America entered World War II. He follows that up with recent clips of people comparing mask and vaccine mandates to Hitler, which leads him to laugh incredulously and introduce a fake game-show segment called “What’s More Hitler?” The tone of that segment will feel familiar, for good or ill, to anyone well versed in Stewart’s Daily Show run. Though Stewart developed a reputation for speaking truth to power — and, to some younger demographics, for being a more trusted news source than non-satiric reporters — there was often a sense of smug dismissal coming from his Daily Show, as if merely pointing out the absurd hypocrisy of someone like a Devin Nunes were enough to defuse him(*). Just look at how delighted he was to skewer Trump’s announcement that he was running for the presidency, clearly believing that relentless mockery would derail that campaign in a hurry. That philosophy has very obviously been proven ineffective in the time since Stewart stepped away, yet that tone still informs his humor on The Problem.

(*) There was also a degree of Both Sides-ism to Stewart’s comedy, made most obviously manifest in 2010 when he and Stephen Colbert hosted the Rally to Restore Sanity and/or Fear. When one of the freedom panelists alludes to it as the “march against insanity or whatever,” Stewart quips, “We won.”  

There’s a lot of well-meaning material in the two Problem episodes critics were given to review. Stewart’s interview with McDonough feels more probing than we often get from straight newspeople who have to worry about future access, even if his questions ultimately hit a bureaucratic brick wall. (Stewart then patronizingly tells McDonough that he believes his concerns for the troops are sincere, prompting the secretary to retort, “The beauty is, I don’t give a shit [what you believe].”) But none of it quite comes together, especially compared to the work done in this area while Stewart’s been absent.

Stewart is fond of joking about how much time has passed not only with regard to his appearance but in terms of how people consume TV. At the end of the premiere, he thanks the audience for watching, then acknowledges that few people will actually watch the show on Apple TV+ versus those who look at aggregated clips online. With its more serious tone and long-planned, single-topic focus, The Problem feels like Stewart’s attempt to evolve what he used to do for a new era. He just hasn’t figured out how to do it yet, and may be too entrenched in his old approach to succeed for anyone beyond the most die-hard Daily Show With Jon Stewart fans.

The premiere of The Problem With Jon Stewart is available now on Apple TV+, with new episodes releasing every other week. 

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