by David Gordon: He is comedy royalty. But the world has changed since he was at the height of his powers…
n march 2021, shortly after Jon Stewart joined Twitter, he tapped the microphone and used his new pulpit to make amends for an infamous act of aggression from his distant past.
“I called Tucker Carlson a dick on National television,” Stewart tweeted. “It’s high time I apologize…to dicks. Never should have lumped you in with that terrible terrible person.”
Stewart originally fired this shot 17 years ago, on October 15, 2004, but if you’re old enough, you surely remember what happened, in part because it was one of the first truly viral political videos of this century. Stewart was a guest on Tucker Carlson’s cacophonous CNN political-argument show, Crossfire, a half-hour nightly migraine of debate-club doublespeak, during which Stewart pleaded with Carlson to “stop hurting America.” “Wait, I thought you were gonna be funny,” Tucker sniffed. “No,” Stewart shot back, “I’m not gonna be your monkey.” Soon enough he was calling Tucker a dick on national television. “You’re as big a dick on your show,” he said, “as you are on any show.”
Tucker Carlson was actually the co-host of Crossfire, along with his left-leaning Clinton-era frenemy Paul Begala, but nobody remembers Begala, and why should they? The whole thing went down in history as Jon Stewart versus Tucker Carlson, with Stewart the champion by first-round knockout. Within months, CNN canceled Crossfire, hurtling Stewart into a position of political influence and superstardom that few comics in America have ever reached. Two weeks after Stewart humiliated Tucker on his own show, President George W. Bush won a narrow reelection over Senator John Kerry, and it would be no overstatement to say that, in the pre-Obama years that followed, the leader of Democratic resistance was Jon Stewart, and he was holding rallies weeknights at 11 p.m Eastern on Comedy Central.
The Bush years, starring Karl Rove, the Machiavelli of direct mail, and Dick Cheney, the wizard behind the curtain, seem almost quaint now, as does the kind of president who would affectionately nickname his top adviser “Turd Blossom.” During his post-presidency, Bush has largely occupied himself with oil painting, not plotting coups. Back then Cheney was as menacing a villain as Democrats could imagine; now his daughter is one of the last Republican bulwarks against Trumpism. Whenever Bush spoke, Democrats pictured Will Ferrell. A genial alpha-blunderer. This was the dawn of social media, and the twilight of a certain era in television. This was Stewart’s golden age. Nothing that followed has come close.
After Barack Obama got elected president, and then reelected, Jon Stewart versus Tucker Carlson on Crossfire had been etched, for the politically obsessed, into the cultural imagination as a moment of triumph against the poison of cable-TV punditry and the culpability of those who partake of it—a live-audience broadcast of history’s arc bending toward justice. So much so that when Stewart stepped aside from The Daily Show for good on August 6, 2015, less than two months after Donald Trump kicked off his candidacy by describing Mexicans as “rapists” and “drug dealers,” his departure seemed a logical bookend. America was in safe-ish hands. The adults were back in charge, and had been for some time. Trump’s candidacy was so cartoonish, it seemed like something cooked up by The Daily Show. Jon Stewart had won.
An honest accounting of how America swerved so unexpectedly requires skipping back in time to that 2004 episode of Crossfire. Was it really a moment of triumph for Jon Stewart? Or was it actually a turning point for the other side? Perhaps what people thought they were watching—Tucker, self-immolating—was in fact the origin story of Tucker Carlson 2.0, the one who’s currently hurting America with a nimbler and far more ruthless brand of demagoguery than he was peddling two decades ago. Humiliation is a powerful motivator. In the same way that Obama’s roasting of Trump at the 2011 White House Correspondents’ Association Dinner supposedly drove Trump to run for president out of spite, Stewart’s prime-time dismantling of Carlson seemed to have unleashed something in the bow-tied menace. He looked like he felt betrayed by the way Stewart revealed the kayfabe with everyone watching. Didn’t he understand that this was all just theater? How dare he pretend he wasn’t playing the same game?
Before Crossfire, remember, Carlson pulled off a reasonable portrayal of a serious journalist. In 1999 he wrote a piercing profile of then–Texas Governor George W. Bush for the premiere issue of Tina Brown’s Talk magazine, in which Carlson flinched in horror after Bush casually mocked a Texas woman on death row who was begging him for clemency. Post-Crossfire, though, Tucker went all in on his nativist act. He turned hating Jon Stewart and everything he represents into a right-wing brand so powerful that even Rupert Murdoch balks at reining him in. For the past six years, during one of the most torturous periods in recent American memory, Stewart was taking his victory laps and frittering away a cushy HBO deal while Carlson devoted himself to polishing his act, live on prime-time television, five days a week, for an audience far bigger than Stewart’s Daily Show ever drew.
The grand return that Stewart finally launched last fall, The Problem With Jon Stewart, streaming on Apple TV+, is hosted by a guy who took a six-year break from television, and boy, does it show. According to the industry-measurement firm Samba TV, the fifth episode of The Problem With Jon Stewart has been streamed just 40,000 times, which is down 78 percent from the pilot, which aired on September 30, 2021. By comparison, HBO’s episode of Last Week Tonight With John Oliver that same week drew more than 800,000 viewers.
Stewart’s specific genius on The Daily Show was layering facts and complexity into jokes, and stitching punch lines together into George Carlin–esque political riffs. When Stewart was at the peak of his powers, no one could pack more ideas into 22 minutes of comedy. But something has turned. Now he’s the one who seems overwhelmed by complexity and prone to oversimplification. He’s the one who gets called out for fumbling facts, for missing the point, for being out of touch. It’s not just that Tucker Carlson has struck back with a Stewart-proof breed of sophistry. It’s not just that topical comedy doesn’t work as well as it used to. The problem with The Problem With Jon Stewart is Jon Stewart himself.
Stewart’s very first brand-name guest on his very first talk show—The Jon Stewart Show on MTV, which premiered nearly 30 years ago on October 25, 1993—was the self-anointed “King of All Media” himself, Howard Stern. Stern, one of Stewart’s comedy mentors, was on hand to promote his new memoir, Private Parts, soon to be a major motion picture also starring Howard Stern. And before he even settled into the couch, before Stewart could get a word in, Stern told him that The Jon Stewart Show was going to get canceled, soon, and that it would take Stewart’s career down with it.
“I’m nervous about this show, I really am,” Stern said, commandeering the interview. “I wanna get the message out about my book before the show is canceled.” Then he addressed the audience—Stewart’s audience. “Does anybody know who Jon is and why I’m talking to him?” This sort of thing is how comics show affection, but Stern also meant every word. “I was offered a talk show on MTV, I’ll be honest with you,” he said, humblebragging before there was a term for it. “And I turned it down, and I’ll tell you why—they ruin people’s careers.”
“Well, Howard,” Stewart said, finally getting in a line. “I didn’t have a career.”
Rewatching the first few episodes, what stands out, besides Stewart’s palpable terror and comically ill-fitting wardrobe, is a budding comedy icon searching for his subject. He had the nebbishy charm of Woody Allen, minus the undercurrent of sexual predation. He was friendly, media savvy (for 1993), and safe around your teenagers. Perfect for MTV. The giants of late-night television—Carson, Letterman, Leno—didn’t come from this world. They weren’t outsiders. For Stewart’s amassing cult audience, his outsiderness was the basis of the appeal. What was this dork even doing here? The optics were subterranean, a secret late-night show operating out of the basement of a late-night show, with a ripped Blues Traveler poster by the stairs and a thumb-hockey board for a coffee table.
Stewart had found his place in the celebrity caste system: the smart aleck, uncool but cool-adjacent, thanks in part to a slate of legitimately hip musical guests, including Ol’ Dirty Bastard and Bad Religion. Stewart’s vibe may have been Woody Allen, but his comic hero was Carlin—the idol-smasher, the conscience of comedy, the impatient gives-no-fucks philosopher-king who took on the government, greedy corporations, and Andrew Dice Clay for telling sexist, homophobic jokes, for punching down.
George Carlin was where Jon Stewart was headed, but he couldn’t be that guy on MTV. He had to get canceled first.
Stern was right, of course, about all of it.
The Jon Stewart Show did get canceled, in less than two years, and it did ruin his career, at least for a little while. He got passed over for hosting jobs. He made the stoner comedy Half Baked with his stand-up pal Dave Chappelle. He got stabbed in the eye by Josh Hartnett in The Faculty. He got miscast in the ensemble love story Playing by Heart as someone who could ever, in his wildest dreams, kiss Gillian Anderson. He had a recurring role on The Larry Sanders Show, Garry Shandling’s brilliant, early-HBO late-night satire, as “Jon Stewart,” Larry’s understudy. For a brief minute, according to an account by the comedian and director Judd Apatow that appears in Chris Smith’s The Daily Show (The Book): An Oral History, Shandling flirted with turning The Larry Sanders Show over to Stewart, but nothing came of it.
Then, in 1998, the executive who’d hired Stewart at MTV, Doug Herzog, called him about a job opening at a nascent cable network called Comedy Central. Craig Kilborn, the fratty cocksure original host of The Daily Show, had gotten his big call-up from CBS to host the late-night slot following David Letterman’s, which was one of two jobs Stewart didn’t get. (The other was replacing Letterman on NBC. That went to Conan O’Brien.) Stewart was interested in the Daily Show gig, Smith reports in his book, but only if he could strip Kilborn’s version, which was funny but often mean-spirited, down to the studs.
You know the rest.
And now, on April 24 at the Kennedy Center, in Washington, D.C., Stewart will receive the Mark Twain Prize for American Humor, which, aside from a series order on HBO, is arguably comedy’s highest honor. In career terms, it is the opposite of getting canceled. It’s canonization. He will be the Twain Prize’s 23rd recipient, joining a list of luminaries that includes Richard Pryor, Steve Martin, Lily Tomlin, Tina Fey, his beloved Carlin, and his buddy Chappelle, and that no longer includes Bill Cosby, whose honor was rescinded in 2018. “I am truly honored to receive this award,” Stewart said in response to the announcement. “I have long admired and been influenced by the work of Mark Twain, or, as he was known by his given name, Samuel Leibowitz.” (Leibowitz is Stewart’s birth name. It’s a Jewish joke and a nepotism joke. I requested an interview with Stewart for this story but he declined.)
The Twain Prize is a classic double-edged sword. The list of winners is short, and the names—to put it in comedy terms—really kill. As Joe Biden might say, it’s a big fucking deal. (You know who doesn’t have a Twain Prize? Howard Stern. Unless he turned that down too.) It also means that your best work is behind you, and soon you’ll need spectacles to see it. No one has ever followed up a Twain Prize with their masterpiece, and Jon Stewart will not be the first. On this count, Twain Prize winners are no Mark Twain. Stewart spent the first three decades of his career expecting failure, assuming that tomorrow would be the day it’d all come crashing down, and instead somehow he managed to go out on top, on his own terms. No wonder he’s seemed lost ever since.
Stewart departed The Daily Show in 2015 after a 16-year run that stretched across three presidencies; the hanging-chad election of 2000; 9/11; the Iraq War; Hurricane Katrina; the election and reelection of Obama; the Great Recession; the awesome stupidness of the Tea Party; the shooting of Michael Brown in Ferguson, Missouri; and the rise of Donald Trump, or at least his descent down that escalator when he announced his candidacy for president. He was already inching away from the show that made him a superstar by 2013, though, when he took a break to write and direct a movie called Rosewater, a thoughtful indie drama based on the true story of an Iranian-Canadian Newsweek reporter who was arrested and held captive for months in 2009 by Iran’s Islamic Revolutionary Guard Corps. Considering it was made by the host of a late-night show, Rosewater turned out admirably well, but it didn’t herald the arrival of a fresh auteur. Also, no one went to see it. John Oliver filled in for Stewart during his sabbatical from The Daily Show, and it was hard not to notice how much more spry Oliver seemed behind his boss’s desk.
Once Trump arrived, Stewart all but vanished. He signed a four-year production deal with HBO that ended in 2020 and produced literally nothing—four years, nothing. There was an animated-shorts series that never happened. A new stand-up special was announced, then never spoken of again. He tried making another movie, a political comedy he wrote and directed called Irresistible, starring the Daily Show alum Steve Carell and Bridesmaids’ Rose Byrne, about two rival campaign strategists locking horns over a small-town mayor’s race, but the finished product feels like the work of someone who realized it was hopeless in the editing room, and maybe even while he was shooting it.
Stewart was entering the lifetime-achievement phase of his career, in other words, and maybe we shouldn’t roll our eyes so easily at only being the voice of one generation. It’s easy to forget now, but there was an inflection point when Comedy Central could’ve easily been the palace of Craig Kilborn and Tosh.0. Stewart dragged The Daily Show—against its will, according to Smith’s oral history—in the opposite direction, and he wound up giving Comedy Central its core identity, not to mention a rack of Emmys, including a remarkable 10 straight for Outstanding Variety Series from 2003 to 2012. Without Stewart’s Daily Show, there’s no Colbert Report, no Last Week Tonight With John Oliver, no Daily Show With Trevor Noah. But maybe no Tucker Carlson Tonight, either.
Stewart could’ve pulled a Jay Leno and hung onto The Daily Show forever. Instead he had the uncommon grace to see the end coming, and to get out before he’d overstayed his welcome. In his heyday, having a “senior Black correspondent” made for biting satire. By the end of his run, it was time for a Black host. His trademark self-deprecation had drifted too far from the reality of his station in life. The richer you get, the more famous you get, the harder it is to be the avatar of populism. His protestations that he had no real power, that he wasn’t part of the establishment, or the mainstream media, stopped ringing true. And for good reason. It’s hard to punch up from the stage of the Kennedy Center.
Maybe that’s what explains his second-act squishiness. After four lost years at HBO, Stewart signed a new deal in 2020 with Apple TV+ and swiftly announced plans to get back to his roots: telling jokes about current events. His new series, The Problem With Jon Stewart, would strike back against what Stewart has described as the arson economy of social media with some room-temperature nuanced conversation. It sounded a lot like The Daily Show, only longer and less funny, and instead of four episodes a week, Stewart was going to deliver just eight episodes per season. Each episode would follow a three-act format: opening monologue, expert roundtable, sit-down interview with someone powerful—the chair of the Securities and Exchange Commission, the Veteran Affairs secretary, the CEO of Shell. If The Daily Show was a parody of a nightly news show, though, The Problem often feels like a defanged Real Time With Bill Maher.
Stewart seemed to be retreating into safe territory, but so what? We can’t all be Bo Burnham, Svengali-ing stand-up specials for other comics, or an Oscar winner like Jordan Peele, or a movie star like Steve Carell, or a sitcom legend like Tina Fey. George Carlin had one short-lived TV show (The George Carlin Show, which lasted 18 months on Fox in the mid-1990s), never directed a movie, never did much more than play himself in movies, and no one thinks his career is incomplete. He was one of the voices of his generation too, and that was plenty.
But he also never phoned it in, not onstage anyway. The Problem With Jon Stewart is a strikingly unambitious, defiantly untimely show that confuses thrift with substance, as though spending money on anything but office furniture is a sign of intellectual unseriousness. During his Daily Show emeritus phase, Stewart took some retroactive flak for the sausage fest in his writers’ room and for trying to remedy the failure with token hires, and to his credit, he copped to the criticism. During a June 2020 interview on the radio show The Breakfast Club, he recalled “going back into the writers’ room” after a critical article in Jezebel “and being like, ‘Do you believe this shit? Kevin? Steve? Mike? Bob? Donald?’ Oh … Uh-oh. Uh-oh.” Now, on his Apple show, he seems to be hyperconscious of reducing his white-male-celebrity footprint. The Problem With Jon Stewart is a multi-platform brand, which is to say there’s also a podcast, a Twitter feed, and a YouTube channel, but it all feels a little dutiful, and though Apple declared the show an immediate hit with viewers, well, do you know any of them? Have you seen even a single viral clip from it?
“I’m having a hard time figuring out what you’re going for,” the New York Times opinion writer Kara Swisher told Stewart in her casually insulting way on a recent episode of her podcast Sway. She called his Apple show “spare.” (“When I say ‘spare,’” she said, really pouring it on, Howard Stern–style, “it is spaaare.”) She brushed off the show’s opening 15 minutes as the “beginning part, where you do your Jon Stewart thing with an audience.” Baffled, she posed the question to him instead: “What do you think you’re going for?”
“I always find that question strange,” he replied. Credit to Stewart—he knew what he was getting into with Swisher and often seemed to enjoy the roasts. “Do we need this? … There’s like five CSIs!” He’s not trying to revolutionize television for the second time. Like many middle-aged men blessed with the good fortune to live out his days in cruise control, he’s just trying to make himself useful. “I always find the self-justifying aspect of it a little odd.”
Then he attempted again to actually answer her question: “If I think noise is the antithesis of progress, [then] what if we tried to make something that was an equalizer? … That tried to bring some clarity to a noisy conversation?” This did not move Swisher, who surely considers it her job to bring clarity to a noisy conversation. She pressed him on why he didn’t turn around a fast episode on Ukraine, settling instead for a months-old rehash of the GameStop saga at a time when the world is facing the greatest threat of nuclear annihilation since maybe 1983. He responded by likening the media to “8-year-olds playing soccer,” an answer that is about as intellectually rigorous as seeing something you don’t like and calling it “fake news” or “clickbait.”
“Not climbing on the moment is an advantage, not a disadvantage, for the types of things we want to talk about,” Stewart had insisted at one point in the conversation. If this just sounds like an excuse for complacency, Swisher seemed to think so too. “I don’t mean to say ‘Has time passed you by?’ but …” she began, then trailed off, which drew a huge cackle from Stewart.
“Yes, time passes all of us by,” he conceded. “I’m not going to pretend that I’m not 60 next year.”
He was defending his Apple show as if it were a cozy pair of Allbirds, the streaming equivalent of a Vegas residency. But the more Swisher pressed, the more wounds she revealed. The Trump era seemed to have rocked his faith in his former profession. He used to believe in the power of comedy to hold politicians and billionaires to account, and in his own power to at least make a dent. But he’s not so sure anymore. “It’s pleasant, it’s a distraction,” he said, “but ultimately feckless.”
For someone about to win the Twain Prize, he sounded awfully defeated. He left The Daily Show seven years ago, and since then, he told Swisher, “almost everything that I believed and advocated for didn’t come to pass, and probably got worse.”
Once upon a time, if you accused Jon Stewart of actually trying to solve problems, of attempting to contribute something more useful than dick jokes, he’d plead dumb comedian—I’m just here to make people laugh! It was insincere then, and now it’s being parroted by Joe Rogan to excuse spreading COVID lies around the world. Yet again Stewart’s tactics have been weaponized by forces of disinformation. Stewart’s reaction, though, has been to drop the veil of comedy altogether. Aside from his Jon Stewart thing at the beginning of The Problem and a few wry asides during interviews, he’s not even trying to be funny. When you take the comedy out of topical comedy, though, you become … the media. (“I think you’re a good comedian. I think your lectures are boring … I do think you’re more fun on your show,” Carlson said to Stewart in that Crossfire appearance, all those years ago. For once, Tucker was telling the truth.)
And as The Problem With Jon Stewart makes clear, funny one-liners and five-minute chats with pliant celebrities aren’t particularly good practice for roundtable conversations with policy experts and extended interrogations of polished CEOs. An early episode that described the U.S. armed services’ continued use of toxic burn pits near military bases culminated in a tense, misbegotten interview with President Biden’s VA secretary, Denis McDonough. Stewart spent 10 minutes repeating himself, grandstanding in circles, arguing with a broken system, and blaming it on the guy who was mere months into the job and was patiently trying to explain the obstacles in his path. If Stewart’s goal was to make his audience feel sympathy for a federal bureaucrat, he nailed it.
More than once already, Stewart has dedicated an entire episode to a subject, only to have an actual expert on that subject call him out for getting it wrong. The first time, a Wall Street Journal editor took exception to the mess Stewart made trying to summarize the GameStop saga—and, seriously, go watch the episode if you want to understand it less than before you watched—and to his portrayal of Redditors as folk heroes schooling the elites. Days later, Stewart got aired out by a Gimlet Media climate-change reporter for having argued, incorrectly, that recycling doesn’t work (plastic recycling doesn’t work; paper and metal recycling work great) and for going too easy on oil companies.
Because this is 2022, Stewart responded by inviting both reporters onto his podcast to hash it out some more. He seemed to bridle against the Journal editor’s suggestion that he was being naive about GameStop, so he doubled down, ranted about the need for more transparency around extremely private financial transactions, then did the Tucker Carlson thing where he accused the journalist of being the naive one. At least with the climate reporter, Stewart conceded his mistakes and wound up having the kind of detailed, enlightening conversation that it sure would’ve been nice to see on his new television show.
If Tucker Carlson is what you get when you detach truth from reality, The Problem With Jon Stewart is what happens when you don’t sew them back together well enough. You can pollute conversations with the best of intentions. You can mislead millions of people while you’re trying to bring some clarity to the conversation. Just ask Joe Rogan. Even Stewart doesn’t use that dumb-comedian line anymore. He knows he needs to do his Jon Stewart thing in order to get our attention, but he doesn’t have much faith in his own shtick anymore against the likes of Donald Trump and Tucker Carlson. He may have won the Twain Prize, but go ask Jon Stewart who he thinks won the fight.