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How seriously should we take Jon Stewart?

The longtime Daily Show host is back on TV, and it’s a little bit weird.

Jon Stewart on the set of The Daily Show in 2015.
Brad Barket for Comedy Central/Getty Images
Constance Grady is a senior correspondent on the Culture team for Vox, where since 2016 she has covered books, publishing, gender, celebrity analysis, and theater.

Jon Stewart is back, and it’s a little bit weird.

Stewart’s new TV series, The Problem With Jon Stewart on AppleTV+, is a news-comedy hybrid, and sort of a loose update of the format Stewart pioneered during his time as host of The Daily Show. But while Stewart always maintained that The Daily Show was meant to be funny first and foremost, The Problem With Jon Stewart wears its comedy with a distinct lack of ease. “I guess that answers whether or not the show’s going to be funny,” Stewart cracks early on, after the debut episode’s very first joke falls flat.

The confusion over whether The Problem With Jon Stewart is funny, or whether it even should be funny, is part of a larger question that has seemed to follow Stewart for his whole career. Stewart built his reputation on using comedy to cut through the sanctimony of conventional journalism and politics to give his center-to-liberal audience the truth about the world. His was a coherent worldview: Politicians on both sides of the aisle are hypocrites corrupted by cash; everyone’s lying about their professed values but especially those idiots who aren’t even willing to follow the science; and the only rational response to all the dishonesty and stupidity of the world is to laugh at it.

Stewart is the man who gave millennials most of their news as they came of age politically; the man who prompted the New York Times to ask in 2008, “Is Jon Stewart the most trusted man in America?” And he did it, always, with a smirk and a wave of his hand, a constant protestation that he was really just out here to tell jokes and make people laugh.

Yet in the aftermath of the Trump administration, it’s no longer clear that the liberal landscape Jon Stewart helped construct was an unalloyed good. Even more crucially, it’s not clear that his continued assertions that he was just a comedian who happened to tell jokes about politics were ever all that honest.

As a result, The Problem With Jon Stewart seems to be haunted by confused questions that no one involved seems to have quite figured out the answers to. Should Stewart still be doing his Daily Show thing? Should he ever have done it? What does it mean to be Jon Stewart — Jon Stewart! The man who taught a generation how to see the world! — and does even Stewart fully understand the platform he has?

For a long time, Stewart was the guy people could trust to tell it like it was. But now it seems like maybe he didn’t understand how it was.

So just how seriously should we take Jon Stewart, anyway? And have we always gotten the answer to that question right?

“We’re the group of fairness, common sense, and moderation”

The Daily Show premiered in 1996, and Stewart took over as host in 1999. During the 2000 election, Stewart’s Daily Show began to acquire its political focus, and by the time the recount began making its way to the Supreme Court, the special appeal of the show had become clear: Jon Stewart, viewers could see, was the only person in the media who was willing to say out loud how absurd the national situation had become.

“We’re still in the middle of either a) a constitutional crisis,” Stewart announced six days after election night in 2000, “or b) the funniest sitcom premise since She’s the Sheriff.”

Part of what’s striking about Stewart’s approach, from the vantage point of 2021, is the lack of outrage. Stewart was willing to emphasize how ridiculous it was that the election depended on a bunch of hanging chads in Florida, but he wasn’t about to make anyone feel like they should drive to the Supreme Court building and protest the decision of Bush v. Gore. For Stewart to harangue or emote about the things he was joking about wouldn’t have been funny; moreover, it wouldn’t have been cool.

In a 2002 interview with the New Yorker, Stewart described the voice he’d developed as the voice of “the disenfranchised center.”

“It comes from feeling displaced from society because you’re in the center. We’re the group of fairness, common sense, and moderation,” he explained. As such, it was not appropriate for him to take sides on polarizing issues, such as gay marriage: “The disenfranchised center doesn’t give a shit.”

Stewart’s easy cynicism and refusal to take sides at the time made The Daily Show feel cool. That stance would also eventually become central to one of the biggest criticisms of his work after the rise of Donald Trump.

“It’s interesting to hear you talk about my responsibility”

The 2000 election codified Stewart’s voice as a satirist. But easily the two most iconic moments of his run at The Daily Show would come when he abandoned the formula.

The first came days after September 11, 2001, when The Daily Show returned to the air after a nine-day hiatus. Stewart opened the show with a monologue, and for once he abandoned the jokes. Instead, his voice trembled as he spoke, and he seemed constantly on the verge of tears. “I wanted to tell you why I grieve,” he began, “but why I don’t despair.”

It was this speech, the New Yorker would later argue, that “established Stewart as someone to trust and turn to, a national figure.” It was in a way a continuation of the brand Stewart had developed in his coverage of the 2000 election: Jon Stewart was the guy who would tell it like it was, even in a time of national tragedy, and even at times when we traditionally look to figures a lot more respectable than late-night cable comedians.

Stewart’s second-most iconic moment as Daily Show host didn’t happen on The Daily Show at all. It happened on CNN’s now-deceased Crossfire, in 2004, and is often remembered as the start of Tucker Carlson’s transformation from conventional right-wing pundit to Fox News provocateur.

Crossfire was a debate-style opinion show that featured conservative and liberal pundits facing off against each other. At the time, Carlson represented the right and former Clinton adviser Paul Begala the left. Stewart appeared as a guest in 2004, ostensibly to promote his new book America (The Book), but he ended up just destroying the program instead. When CNN CEO Jonathan Klein announced a few months later that he’d be canceling Crossfire, he directly cited Stewart’s appearance to explain the decision.

Stewart’s beef with Crossfire was that it pretended to be a debate of ideas when in fact, making such a claim was “like saying pro wrestling is a show about athletic competition,” he said. Crossfire, Stewart argued, was entertainment dressed up as straight news, and as such, it ended up inflaming and infuriating the audience it was ostensibly meant to inform. “You guys are hurting America,” Stewart told Carlson and Begala. He also called Carlson a dick and got in a dig at Carlson’s then-signature accessory: “How old are you? … And you wear a bow tie?”

In 2004, YouTube didn’t exist, and neither did Twitter, but Stewart’s Crossfire appearance nonetheless spread wildly across the internet. It was in a way an early prototype for the kind of clip aggregation post that a thousand digital media ventures would harvest for clicks in the decade to come: “WATCH Jon Stewart DESTROY Tucker Carlson and his douchey bow tie for 14 minutes straight!!”

Like Stewart’s post-9/11 speech, the Crossfire interview still works as profoundly compelling TV. Both moments are cathartic in the way an Aaron Sorkin monologue is cathartic, only with more edge; they are satisfying in a way that good TV rarely gets to be anymore, in our own vexed and furious age. They further established Stewart as someone you could count on to use his platform to really speak truth to power.

There was a tremendous capacity for influence, it seemed, in mixing comedy with news: what righteousness the combination generated, what honesty, what purity of conviction. That’s part of why, in 2007, a poll from the Pew Research Center found Stewart tied for fourth place in a list of America’s most trusted journalists, along with Brian Williams, Tom Brokaw, Dan Rather, and Anderson Cooper.

Viewers trusted Jon Stewart more than most reporters because only Jon Stewart was willing to be that honest. He said it all to Tucker Carlson’s face, and to his bow tie too.

Stewart himself often mocked the idea that people should take him seriously as a journalist. During that infamous Crossfire interview, Carlson attempted to fight back against Stewart by noting that when then-presidential candidate John Kerry appeared as a guest on The Daily Show, Stewart threw him softball questions. Wasn’t Stewart, Carlson argued, just as bad as Crossfire? Who was he to criticize Carlson and Begala, when he was failing his own responsibility to ask Kerry hard-hitting questions about real issues that mattered?

“It’s interesting to hear you talk about my responsibility,” Stewart replied. “I didn’t realize — and maybe this explains quite a bit — that the news organizations looked to Comedy Central for their cues on integrity.” When Tucker tried to continue his line of questioning, Stewart again pointed to his home network. “You’re on CNN!” he said. “The show that leads into me is puppets making crank phone calls.”

Stewart wasn’t supposed to be America’s source for news, was his position. He was a comedian, and it was not his job to follow journalistic ethics or to do anything particularly meaningful with his platform beyond plead for better work from the press corps he satirized. He never asked to be one of the primary sources on current events for 21 percent of people under 30. If the news was entertainment these days — well, that wasn’t his fault.

The line played well in the moment, and Stewart has continued to repeat variations upon it again and again throughout his career. But it’s striking how few people, including Stewart’s most dedicated fans, truly seemed to believe it.

“It’s strange, isn’t it ... a man who lives to clarify resorting to loophole”

In a profile of Stewart for Esquire in 2011, Tom Junod called Stewart’s continued position that he was just a nobody late-night cable host with no real influence over the world “that denial of power upon which his power depends.”

“It’s strange, isn’t it,” Junod continued. “One of the fastest and most instinctive wits in America feeling it necessary to go on explaining himself again and again; a man who lives to clarify resorting to loophole; the irrepressible truth-teller insisting on something that not one person of the two hundred watching his show in the studio — never mind the millions who will watch on television — can possibly believe.”

The truth was, Junod concluded, “Stewart’s just a comedian the way gunslingers in old westerns are really peaceable sodbusters who hate all that bloodshed and all that killin’ but finally have to strap on them six-guns and march on into town.” Stewart had made himself into the hero of the media landscape. His protestations that he was just a comedian were all part of that heroic pose, the first act “refusal of the call.” “Heck,” Junod mused, “he’d go back to telling jokes if he could, but he can’t, not with hired guns like Tucker Carlson and Jim Cramer around.”

Jon Stewart denied wielding any real power over his audience, having any journalistic responsibilities, because The Daily Show aired right after Crank Yankers. But everyone knew that Stewart’s fans didn’t watch him in the same way they watched Crank Yankers. They watched him to experience that pure, incredible moment, the moment where Stewart told the truth, where he told it like it was. The moment where he spoke truth to power.

That was where Stewart acquired his power, his intoxicating sway over his audience. (That audience, it’s worth noting, was mostly male, mostly liberal, mostly young, and mostly college-educated.) Stewart’s viewers trusted him — they made him for a while perhaps the most-trusted man in America — because they knew he would tell them the truth as he understood it, in an era when both the White House and the media were failing badly to report the truth. When liberals watched The Daily Show during the Bush era, for just a half-hour a day, they would see reality reflected back at them from their TV screens, not ever-more esoteric debates about hanging chads and WMDs of dubious existence. And they would feel safe and sane again.

Almost 20 years after that infamous Crossfire episode, the balance of power has shifted. Tucker Carlson is now one of the biggest names on Fox News, beaming his particular brand of conservative propaganda into millions of homes every nights, with the power to almost single-handedly politicize masks and vaccines, to drive harassment campaigns, to shape the way an enormous segment of the country understands reality.

Jon Stewart is just now returning to television after a six-year absence, having skipped the Trump years almost entirely. His new show is one among many news-comedy hybrids, lots of them staffed by former Daily Show correspondents, most of them admired by liberal America, and few of which seem to make any profound difference to the nation or world.

A fair question to ask is: Did the catharsis Jon Stewart offered to his viewers last? And was it worthwhile to offer it in the first place?

“Not being able to distinguish between real racists and Tea Partiers is an insult”

During the 2010 midterm elections, Stewart held a rally with Stephen Colbert on the Washington Mall. It was called the Rally to Restore Fear and/or Sanity, with Stewart pleading for sanity and Colbert for fear. Over 100,000 people showed up, and for most of the day, the event was just a very straightforward and hip concert. The Roots performed, and so did John Legend.

Then Stewart took the mic in a rare moment of earnestness. He gave a speech that would serve as the thesis for the rally, and as a thesis of sorts for Stewart’s version of The Daily Show, too.

The media had inflamed America’s political disagreements, Stewart said, by blowing up what he believed to be essentially small issues into existential problems. “There are terrorists and racists and Stalinists and theocrats, but those are titles that must be earned; you must have the resume,” he explained. “Not being able to distinguish between real racists and Tea Partiers, or real bigots and Juan Williams or Rick Sanchez is an insult, not only to those people, but to the racists themselves, who have put in the exhausting effort it takes to hate.”

The democratic ideal, Stewart concluded, was to treat politics like traffic merging into the Lincoln Tunnel. “These millions of cars must somehow find a way to squeeze one by one into a mile-long, 30-foot-wide tunnel carved underneath a mighty river. Carved by people who, by the way, I’m sure had their differences,” he said. “And they do it. Concession by concession. You go, then I’ll go. You go, then I’ll go. You go, then I’ll go. Oh my God, is that an NRA sticker on your car? Is that an Obama sticker on your car? Ah, well that’s okay, you go, then I’ll go.”

Plenty of reasonable people would have argued even in 2010 that any distance between “the real racists” and the Tea Party, which by 2018 would be all-in for Trump, was at best academic. The Obama era saw the radicalization of the right and the mainstreaming of a fringe movement driven by racial animus, and Stewart was right in the middle of it. Still, his central message was the same one he’d developed back in 1999 as the voice of the disenfranchised center: Both sides are equally annoying, so why give a shit who’s right? Make some compromises, tell the truth, and move on with your life.

The rally received mixed reviews. One commenter called Stewart’s speech proof that “we’re not alone in feeling as if our general moderate voice of reason isn’t being properly represented in the media, which has become more and more complicit in helping add a powerful element of professional-wrestling sensationalism and confrontationalism to the sociopolitical atmosphere of our nation.”

At Esquire, Junod called it “the biggest celebration of political powerlessness in American history.”

“Thank you, Donald Trump, for making my last six weeks my best six weeks”

Stewart’s last episode as host of The Daily Show aired August 6, 2015, the night of the first 2016 Republican presidential primary debates, with then-candidate Donald Trump onstage. Stewart said nothing about Trump that night, but he’d said plenty two months before, when Trump announced his candidacy.

“I heard some interesting … let’s call it news, today, about a certain, let’s say, gift from heaven, entering the presidential race,” Stewart said gleefully. He swept rapidly over a Hillary Clinton rally (“Pick up the pace, there’s a crazy person running for president! … Anyway, she’ll do great.”) and a Jeb Bush rally (“Are we done yet?”), before he made it to Trump.

“It’s amazing! America’s id is running for president! Trump is like the part of your brain at 3 am that’s like, ‘C’mon, let’s go take a dump in the mailbox. Who’s gonna know?’” Stewart crowed. “Thank you, Donald Trump, for making my last six weeks my best six weeks. He’s putting me in some kind of comedy hospice where all I’m getting is this great morphine.” The segment closed with Stewart along with some of his correspondents faking orgasms at the thought of a Donald Trump presidential candidacy. What comedy gold it was sure to be.

Stewart’s treatment of Trump then was par-for-the-irreverent course at the time. Stewart took no one seriously, so why should he take someone as obviously absurd as Trump seriously? What would be funny about that?

Over the course of the next year, for the post-Stewart Daily Show and its left-leaning comedy-news show peers, Trump’s candidacy rapidly came to seem less and less funny. And when he eventually won the presidency, a new narrative began to set in: The mainstream media and the left never should have mocked someone so dangerous to begin with. They should have seen him as the threat he was from the beginning. Trump should have been taken seriously, but not literally. The left got smug — and endless Daily Show clips were part of how it got that way.

The Daily Show … more than any other thing advanced the idea that liberal orthodoxy was a kind of educated savvy and that its opponents were, before anything else, stupid,” wrote Emmett Rensin in a Vox essay that would become an influential expression of this idea. “The smug liberal found relief in ridiculing them.”

Stewart was in an odd, vexed position. As American politics went white-hot with rage from both sides during the 2016 election, Stewart seemed to be simultaneously too middle-of-the-road and too elitist.

On the one hand, he had spent so long advocating for a bipartisan politics, a politics that was willing to overlook some light racism here and there (racism that was not exactly real, as long as “real” was defined by a white person), in the name of getting things done. This stance was coming to look dangerously naive after eight years of Republican obstructionism against Obama and the GOP’s open-armed embrace of Donald Trump. On the other hand, Stewart had also dedicated segment after segment of The Daily Show to mocking the right and its supporters in small-town red-state America as uneducated hicks.

“Jon Stewart, with his brand of left-leaning cynicism (sprinkled with occasional earnestness), is a bad example for the liberals who watch and love him,” concluded Jamelle Bouie at Slate. “The natural response to all of this is a version of Stewart’s protest—He’s just a comedian—and a refrain from The Dark Knight: Why so serious? The answer is easy: He’s influential. And for a generation of young liberals, his chief influence has been to make outrage, cynicism, and condescension the language of the left.”

Stewart, it seemed, had stepped off the national stage just in time to see his entire comedic ethos come to seem insupportable.

“Our increasingly traumatic times”

It’s not quite correct to say that Jon Stewart sat out the Trump era entirely. He released one film in 2020: a political satire called Irresistible that attempts to call out the political press corps for its cynicism and offer a defense of much-maligned red-state America. It was, critics concluded, a failure, and dated to boot, with a thesis the New York Times suggested was “too unsophisticated for our increasingly traumatic times.”

Irresistible tells the story of a small-town military veteran who goes viral when he makes a heartfelt speech against cutting benefits for undocumented immigrants. Big-player Democratic operatives consider him irresistible bait (get it?) and convince him to run for mayor, and soon major political players are descending from far and wide, turning the whole election into a media circus.

Here’s the big twist (spoilers follow): The whole thing was a setup. Everyone in town worked together to concoct the scheme and stage the viral speech in the hope of luring political strategists to town and getting them to pour money into super-PACs. The town then absconds with the money and uses it to invest in its infrastructure. You thought Irresistible was a movie about cynical politicians taking advantage of a small town, but it’s actually about the citizens getting one over on the politicians.

In Irresistible’s final scene, we see two comic relief characters analyze the whole grift. Stewart has spent the whole movie presenting them to us as unsophisticated rubes, but the punchline of the scene is that they have a media-savvy take on what just went down.

“You know what the problem is, is the media is completely complicit,” says one of them.

“Oh yeah, it’s like Postman says in Amusing Ourselves to Death,” responds the other, citing media theorist Neil Postman’s influential 1985 book, which argues that TV news exists to sell ads. “The news has become entertainment. It’s terrible.”

The gag somehow seemed to unite both positions of Stewart’s that had come to feel behind the times during the Trump era: First of all, isn’t it hilarious to make fun of these uneducated hicks? And second of all, don’t you think you spend too much time making fun of those uneducated hicks?

In fact, one of the most striking things about Irresistible is how much it repeats the arguments Stewart made again and again on The Daily Show. In many ways, it’s a feature-length adaptation of the argument he made on Crossfire in 2004. He began the Crossfire segment by complaining about the way CNN begins its debate coverage by talking to political consultants on Spin Alley, and ended it with a sweeping condemnation of spectacle-focused media. Irresistible, in turn, begins with a fantasy sequence in which political consultants on Spin Alley break format by actually telling the truth, and ends with an Amusing Ourselves to Death gag.

These are all arguments Stewart has been making for more than 20 years now. So the question is, are they still relevant or valuable when there’s a pandemic and when police are still shooting Black people in the street?

It’s not exactly that we’ve fixed the issues Stewart is talking about since he first sat down behind the Daily Show desk in 1999 — but things have just gotten so much worse since then. You’d be forgiven for thinking that Stewart’s approach feels like complaining about a black mold problem when the whole house is on fire.

It all feeds the sense that Stewart’s obsession with the problems of both sides keeps him from marshaling the political energy he is capable of amassing in effective directions. That he keeps squandering it on easy cynicism instead.

“You’re not prepared for that moment to have no impact”

The Problem With Jon Stewart has the luxury of premiering post-Trump, in the comparative calm of the Biden era. Moreover, it is focused on demonstrably real problems.

It struggles, however, with the same problem that has always vexed Jon Stewart: Is this show supposed to kick-start change? Is it supposed to be a news show? Or is it supposed to just be funny?

Stewart has obviously thought about those questions. But he doesn’t seem to have come to any clear conclusions.

“Your purpose can’t be efficacy,” he told the New York Times, when faced with the question of whether his particular brand of political satire can change anything. “Your purpose has to be, what’s the best iteration of this idea? How do we best execute our intention? That’s the whole purpose of making things.”

But that position belies the unstated and deeply idealistic tenet of liberalism that lay underneath Stewart’s satire all along: If you simply make it clear enough that those who have power are lying to those who don’t, you will have an effect. You state your case in the marketplace of ideas, and if you do it well enough, people will buy your idea and discard the old bad ones. You go on Crossfire and you explain why they’re wrong, and you do it so well that they cancel the show. That’s how it works.

Stewart made his case for the so-called disenfranchised center very, very well. But in the long term, it doesn’t seem to have offered anything but a momentary catharsis to people who already agreed with him, while engendering a sense of lazy smugness that’s proven hard to shake. That’s a legacy he is still grappling with.

“The ethos of ‘The Emperor’s New Clothes,’ that always spoke to me,” Stewart told the New York Times this September. “The idea that when there was a group delusion or a spell to be broken, that you could break it with an honest assessment or a funny dagger or something along those lines. And you would say, ‘Hey man, this [expletive] is naked.’ And everyone would go, ‘Oh my god, that’s right, the tyranny is over.’”

But as the Trump era showed, that’s not what actually happened when Stewart pointed out that the emperor’s clothes were off.

“You never expect that you live in a world where the boy would say, ‘But the emperor is wearing no clothes!’ And everyone would turn and say, ‘You’re the enemy of the people! That’s fake news! You run a pedophile ring out of a pizza shop!’” Stewart went on. “You’re like, wait, what? You’re not prepared for that moment to have no impact.”

So Stewart is now left performing a new version of the dance he used to do back when The Daily Show was on, when he constantly and simultaneously insisted on his own righteousness and influence and on the idea that he was just a nobody comic filling time for a network full of puppets who make crank calls. In 2021, Stewart insists that the platform he offers his guests on The Problem With Jon Stewart is the most concrete thing he can do to change the world, while at the same time maintaining his powerlessness.

“I don’t think we can ever lose sight of the fact that it’s still just TV,” he told the New York Times. “Don’t be fooled that this momentary boost is somehow akin to change or effective activism. If it gives those individuals a quick boost and it helps them get over the hill, boy, that would be amazing but those hills — I don’t know if you’ve noticed, we’re all Sisyphus. I’d rather feel like the person pushing someone up than the person kicking them back down.”

Stewart ended this argument with a question that seems to cut to the core of all he does. “Isn’t some small measure of comfort and support and entertainment and insight better than noise and exploitation?” he asked.

For most of Stewart’s run on The Daily Show, his audience would have answered that question with an immediate and enthusiastic “yes.” But after everything that has come since — after the failure of the liberal landscape that Stewart helped to build, after white supremacists marching in the streets, after Donald Trump in the White House as a personal fuck-you from red-state America directly to all those smug elitists like Jon Stewart, after an insurrection at the Capitol — after all that, well.

Is it better?