Television

Jon Stewart’s New Show Isn’t Very Funny. That’s What Might Make It Great.

The Problem With Jon Stewart starts in a defensive crouch, but it’s better when it lets things get messy.

Jon Stewart sits at a desk and gesticulates in front of a display reading, "The Problem With War."
The Problem With Jon Stewart. Apple TV

Having inspired a huge subgenre of political comedy, Jon Stewart, who walked away from The Daily Show in 2015, has returned to television in a determined but defensive crouch. That he’s both worried about and preemptively rebelling against criticism is evident in the extremely ’90s credit sequence that introduces his new weekly AppleTV+ show, The Problem With Jon Stewart. Over grinding, Rage Against the Machine­­­–style guitars, the credits cycle through unflattering potential titles like The Money Grab With Jon Stewart before landing on a title that both sets up the show’s format—each weekly episode deals with a central problem, like “War” or “Freedom”—and preempts the title of skeptical think pieces. Stewart plays defense as host too, alluding early and often to how old he looks and to how little his audience is laughing. Concerns that The Problem’s writing staff might be too white and male, like The Daily Show’s, are staved off by literally showing us Stewart bantering with his staff, which is admirably diverse. That behind-the-scenes footage also seems to announce an intention to be less polished, messier, and more meta. In one of these brainstorming sessions, Stewart openly addresses what he sees as the show’s basic challenge, namely, that a comedy hybrid show about stuff he actually takes seriously is tricky to reconcile with the fact that one idea on the writers room whiteboard is “snake penis.”

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He’s not wrong. That is a problem for any such show, and The Problem With Jon Stewart hasn’t figured it out—which is weird, honestly, because while this could and would trip up many a TV personality, it shouldn’t be an issue for him! Stewart famously perfected an Emmy-winning formula that married comedy and serious political news. He was huge. His influence, for all that he insisted in interviews that he was a joke and a clown, is hard to overstate and of course helped bring about a flock of conceptually similar shows that differ somewhat in approach and execution, including Wyatt Cenac’s Problem Areas, Last Week Tonight With Jon Oliver, Full Frontal With Samantha Bee, and even Seth Meyers’ segment “A Closer Look.”

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It’s true that the formula may, in hindsight, have had some flaws. A generation or more of Comedy Central viewers came to consciousness about current events by watching Stewart lethally and expertly skewering political actors. He did this so successfully, with such precise and well-chosen juxtapositions, that he sometimes in retrospect—at least according to his critics—overshot the mark, transmogrifying the outrageous into the merely grotesque or absurd. Back in 2012, Steve Almond argued in the Baffler that Stewart modeled a form of political engagement that neutered political anger by creating a communal space where the bad guys were so self-evidently ridiculous that there was no real need for civic activism; complacent chuckles would suffice. He took particular issue with Stewart’s habit of emphasizing civility as a fundamental value and the facile centrism with which he insisted—and still insists—that “both sides have their way of shutting down debate.”

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By way of example, Almond describes a 2010 exchange between Stewart and Rachel Maddow in which he took issue with her referring to George W. Bush as a “war criminal.” “Now that may be technically true,” Stewart said. “In my world, a war criminal is Pol Pot or the Nuremberg trials. … But I think that’s such an incendiary charge that when you put it into conversation as, well, technically he is, that may be right, but it feels like a conversation stopper, not a conversation starter.” “This is the Stewart credo distilled,” Almond wrote. “Civility at any cost, even in the face of moral atrocity.”

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I wasn’t convinced by this at the time—I liked Stewart and was pretty pro-civility myself—but I think subsequent events have proved Almond right. Stewart was an artist, but his medium demanded round edges. He could channel his outrage hilariously and powerfully in his monologues, which were never less than crisp and perfectly timed, and pivot with ease to the interview. The effect was smooth, digestible. Even when the guest was an adversary, there was bouncy good humor to the whole enterprise; after a little sparring, Stewart would wrap up with a “Bill O’Reilly, everyone!” that genially defanged any preceding confrontation. Each half-hour was rigorously structured: The commentary had an arc; the interview had a shape. However distressing the news imparted therein might have been, a Daily Show episode felt like a fully digested thought. You could let it go.

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This is not true of The Problem With Jon Stewart. The two episodes made available to reviewers are fascinatingly unpolished. Stewart’s monologue in the first episode, “War,” gets few laughs for good reason: It’s not punchy or precise, and it lacks that Stewart rhythm we’ve all come to expect. A behind-the-scenes discussion between the writers of how the show will be structured feels necessary, if only to orient the audience, but turns out not to really hold for the second episode, “Freedom.” Whereas a typical correspondent’s interview in The Daily Show was skillfully edited to make politicians look like absolute idiots—in a way that could feel mildly comforting, if only because the segments were so definitive and irrefutable—the interviews in The Problem With Jon Stewart are sort of upsetting and shapeless.

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This isn’t exactly bad. In the first episode, Stewart interviews a number of veterans who were exposed to burn pits in Afghanistan—literal trash fires that can cover a base in toxic smoke—but were ignored by the Department of Veterans Affairs when they got sick. The episode explores how military spending, which goes almost unaudited when it comes to waging war, gets bureaucratic and slow when it comes to veterans’ health, refusing to tie the robust science that exists on how toxic substances like dioxin and benzene make people sick to the illnesses these veterans are dying from. That said, the story is messily told. (It’s hard, frankly, not to think about how much more skillfully John Oliver would have done it.) It’s also an issue Stewart has famously cared about for a long time, and the episode suffers a little bit from his overfamiliarity. The veterans and spouses he interviews speak well, but some are naturally nervous, and Stewart doesn’t direct the conversation as much as he could.

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It’s an interesting departure from the kind of aggressively architected segment that packs a point. It could almost be a podcast, were it not for the fact that Stewart is plainly conscious that the format—a panel in front of an audience—is at odds with the execution. More than once, he tries to explain away the audience’s silence as them being “stunned” by what the vets are saying. That’s possible, but they might also just be mildly confused by the tone—or trying to grasp just how badly off the assembled guests are. When Stewart says that one of them, retired Staff Sgt. Wesley Black, has Stage 4 colon cancer, for instance, I was jolted by big questions—wait, Stage 4? My god, we’re hearing from a man who’s dying? How is he now? How long does he have? The brutal stakes of his case aren’t clearly explained up front, and Black doesn’t get to speak until almost everyone else has. Stewart is so deferential and euphemistic about his condition that it falls to the man himself, at the end of the segment, to make the situation clear: “It is too late for me,” he says, twice, before talking about how his family will have to live without him, and with the memory of how much he’s suffered for five years because his symptoms were misdiagnosed.

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After that segment, in which a deeply pained Stewart tries to interject a little levity when he remembers that this is a “comedy hybrid” show, there’s another interview. This one is with Denis McDonough, the secretary of veterans affairs, and it’s awkward for a whole different set of reasons.* The interview doesn’t seem to be edited much at all and features Stewart—who points out that he never once went out and interviewed someone like this when he was at The Daily Show—doggedly asking McDonough what it will take to get these vets health care. It’s uncomfortable watching precisely because Stewart does not let civility prevent him from repeating the question, over and over, until the viewer begins to cringe. We’re used to a journalist asking a question once or maybe twice and moving on. Stewart just keeps asking, and the segment only ends when Stewart is told he can ask just one more, and does. This is not cathartic. It is frustrating and weird to watch in a possibly productive way. One comes to share Stewart’s frustration that the question doesn’t seem answerable. No laugh comes to relieve that anxiety, and Stewart’s concluding remarks don’t do much to offer any sense of resolution or closure.

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In the end, this is the same Stewart from the early 2000s. His orientation toward current events still feels rooted in a post-9/11 moment right down to his mode of argumentation, which—though Stewart is clearly liberal—is clearly pitched to a reasonable bipartisan audience he still seems to believe exists. He starts off his monologue in “War” talking about how both parties talk a good game about supporting the troops but don’t, having apparently failed to notice that neither right nor left these days talks much about the troops at all. Has Stewart noticed that the “Support the Troops” version of 9/11 patriotism has given way to other, more divisive mottos, like “Back the Blue”? His political commentary, in short, feels a tad Rip Van Winkle–ish. He’s still showing clips of Reagan saying something Republican anti-vaxxers contradict, as if hypocrisy charges worked or mattered. Has he noticed that those gotchas presume a sense of shame that the Republican Party has long since obliterated?

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But there is a difference even if Stewart’s outlook feels trapped in amber, and it’s both the reason the show might be having trouble finding its footing and the reason I hope it does: Stewart’s guests now aren’t polished politicians and charismatic stars and authors. They’re people in real peril. In the second episode, “Freedom,” Stewart interviews people who have been persecuted by their governments. One of them, Maria Ressa, is speaking from the Philippines, which she cannot leave, and where she faces a possible sentence of life in prison. That’s hard to joke about.

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The Problem With Jon Stewart isn’t very funny. As one of my colleagues put it, reflecting on how Stewart’s descendants are doing his schtick better than he is, “It’s like the master became the student.” But Stewart might be attempting something messier and more serious than his former work. He’s trying to grow up. Stewart used to insist he was just a comedian whenever he was holding others—like Tucker Carlson in that famous Crossfire interview—to higher standards. For better and worse, he’s not using that excuse anymore.

Correction, Oct. 1, 2021: This piece originally misspelled Denis McDonough’s first name.

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