The Problem With Jon Stewart has the potential to be great because it's so unfunny and unpolished

Slate

One of the criticisms of Jon Stewart's Daily Show tenure is that it emphasized civility. "A generation or more of Comedy Central viewers came to consciousness about current events by watching Stewart lethally and expertly skewering political actors," says Lili Loofbourow. "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.'.... 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. 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." Loofbourow adds: "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."

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• The Problem With Jon Stewart is essentially a news show: "That might be why The Problem With Jon Stewart is rarely funny," says Sophie Gilbert. "You can almost feel for Apple, having landed one of the true groundbreaking forces in late-night comedy only to find that he’s now a slightly more wisecracking version of Dan Rather."
• The Problem is light years beyond The Daily Show territory: "Stewart isn't interested in either mocking his interview subject or himself, and his show's long runtime lets him keep the conversation mostly intact," says Sam Machkovech. "You'll watch (Veterans Affairs secretary Denis) McDonough try, but fail, to run circles around Stewart. The secretary offers tons of empathetic rhetoric for US vets, but Stewart's format opts not to lop any of those lines off as nice-sounding pledges to veterans. We instead hear those lines repeated without satisfying answers to Stewart's clear and fair questions. The result isn't funny, but it sure is fantastic."
• The Problem raises the question: Do we need this?: "As a greying, unshaved Stewart jokes in the opening seconds of the first episode: 'I've been away from television for some time, and before we get started, I really wanted to address the elephant in the room — this is what I look like now.' The joke, one of multiple bits of self-referential metahumor over the course of the show, stands as a tacit acknowledgement that The Problem is, in many ways, a slightly older version of what came before," says Rafi Schwartz. "That's not a bad thing, per se, but it hardly stands as justification for why this, and why now. The inversion from 'comedy first, then issues' to 'issues, with a spoonful of sugary laughs to help the medicine go down' too only serves to highlight just how weird the whole endeavor feels, particularly given the number of Daily Show offshoots that already occupy the same space, like John Oliver's Last Week Tonight and Samantha Bee's Full Frontal. It's not that The Problem is bad. Far from it: The issues are serious and are given appropriate consideration and humanity, plus the jokes are for the most part pretty funny. Nevertheless, the show reminds me a bit of the feeling I get when an old wrestler is brought out of retirement to fight a new class of grapplers. Sure they've got all the moves, the flair, and the goodwill built up from years as a star, but it quickly becomes clear that the game has moved past where it once was, and what was once considered ahead of the curve has since been lapped by the very zeitgeist it helped create."