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How Jon Stewart Misplaced His Edge


In March 2021, shortly after Jon Stewart joined Twitter, he tapped the microphone and used his new pulpit to make amends for an notorious act of aggression from his distant previous.

“I referred to as Tucker Carlson a dick on Nationwide tv,” Stewart tweeted. “It’s excessive time I apologize…to dicks. By no means ought to have lumped you in with that horrible horrible particular person.”

Stewart initially fired this shot 17 years in the past, on October 15, 2004, however for those who’re sufficiently old, you absolutely bear in mind what occurred, partially as a result of it was one of many first actually viral political movies of this century. Stewart was a visitor on Tucker Carlson’s cacophonous CNN political-argument present, Crossfire, a half-hour nightly migraine of debate-club doublespeak, throughout which Stewart pleaded with Carlson to “cease hurting America.” “Wait, I assumed you had been gonna be humorous,” Tucker sniffed. “No,” Stewart shot again, “I’m not gonna be your monkey.” Quickly sufficient he was calling Tucker a dick on nationwide tv. “You’re as huge a dick in your present,” he mentioned, “as you might be on any present.”

Tucker Carlson was truly the co-host of Crossfire, alongside together with his left-leaning Clinton-era frenemy Paul Begala, however no one remembers Begala, and why ought to they? The entire thing went down in historical past as Jon Stewart versus Tucker Carlson, with Stewart the champion by first-round knockout. Inside months, CNN canceled Crossfire, hurtling Stewart right into a place of political affect and superstardom that few comics in America have ever reached. Two weeks after Stewart humiliated Tucker on his personal present, President George W. Bush received a slim reelection over Senator John Kerry, and it could be no overstatement to say that, within the pre-Obama years that adopted, the chief of Democratic resistance was Jon Stewart, and he was holding rallies weeknights at 11 p.m Jap on Comedy Central.

The Bush years, starring Karl Rove, the Machiavelli of unsolicited mail, and Dick Cheney, the wizard backstage, appear virtually quaint now, as does the sort of president who would affectionately nickname his prime adviser “Turd Blossom.” Throughout his post-presidency, Bush has largely occupied himself with oil portray, not plotting coups. Again then Cheney was as menacing a villain as Democrats may think about; now his daughter is likely one of the final Republican bulwarks in opposition to Trumpism. Each time Bush spoke, Democrats pictured Will Ferrell. A genial alpha-blunderer. This was the daybreak of social media, and the twilight of a sure period in tv. This was Stewart’s golden age. Nothing that adopted has come shut.

After Barack Obama acquired elected president, after which reelected, Jon Stewart versus Tucker Carlson on Crossfire had been etched, for the politically obsessed, into the cultural creativeness as a second of triumph in opposition to the poison of cable-TV punditry and the culpability of those that partake of it—a live-audience broadcast of historical past’s arc bending towards justice. A lot in order that when Stewart stepped apart from The Day by day Present for good on August 6, 2015, lower than two months after Donald Trump kicked off his candidacy by describing Mexicans as “rapists” and “drug sellers,” his departure appeared a logical bookend. America was in safe-ish fingers. The adults had been again in cost, and had been for a while. Trump’s candidacy was so cartoonish, it appeared like one thing cooked up by The Day by day Present. Jon Stewart had received.

An trustworthy accounting of how America swerved so unexpectedly requires skipping again in time to that 2004 episode of Crossfire. Was it actually a second of triumph for Jon Stewart? Or was it truly a turning level for the opposite facet? Maybe what folks thought they had been watching—Tucker, self-immolating—was in truth the origin story of Tucker Carlson 2.0, the one who’s at present hurting America with a nimbler and much more ruthless model of demagoguery than he was peddling 20 years in the past. Humiliation is a strong motivator. In the identical method that Obama’s roasting of Trump on the 2011 White Home Correspondents’ Affiliation Dinner supposedly drove Trump to run for president out of spite, Stewart’s prime-time dismantling of Carlson appeared to have unleashed one thing within the bow-tied menace. He regarded like he felt betrayed by the way in which Stewart revealed the kayfabe with everybody watching. Didn’t he perceive that this was all simply theater? How dare he faux he wasn’t enjoying the identical recreation?

Earlier than Crossfire, bear in mind, Carlson pulled off an affordable portrayal of a severe journalist. In 1999 he wrote a piercing profile of then–Texas Governor George W. Bush for the premiere situation of Tina Brown’s Speak journal, through which Carlson flinched in horror after Bush casually mocked a Texas lady on loss of life row who was begging him for clemency. Publish-Crossfire, although, Tucker went all in on his nativist act. He turned hating Jon Stewart and every part he represents right into a right-wing model so highly effective that even Rupert Murdoch balks at reining him in. For the previous six years, throughout one of the vital torturous durations in latest American reminiscence, Stewart was taking his victory laps and frittering away a comfortable HBO deal whereas Carlson devoted himself to sharpening his act, dwell on prime-time tv, 5 days per week, for an viewers far greater than Stewart’s Day by day Present ever drew.

The grand return that Stewart lastly launched final fall, The Downside With Jon Stewart, streaming on Apple TV+, is hosted by a man who took a six-year break from tv, and boy, does it present. In response to the industry-measurement agency Samba TV, the fifth episode of The Downside With Jon Stewart has been streamed simply 40,000 instances, which is down 78 % from the pilot, which aired on September 30, 2021. By comparability, HBO’s episode of Final Week Tonight With John Oliver that very same week drew greater than 800,000 viewers.

Stewart’s particular genius on The Day by day Present was layering details and complexity into jokes, and stitching punch strains collectively into George Carlin–esque political riffs. When Stewart was on the peak of his powers, nobody may pack extra concepts into 22 minutes of comedy. However one thing has turned. Now he’s the one who appears overwhelmed by complexity and liable to oversimplification. He’s the one who will get referred to as out for fumbling details, for lacking the purpose, for being out of contact. It’s not simply that Tucker Carlson has struck again with a Stewart-proof breed of sophistry. It’s not simply that topical comedy doesn’t work in addition to it used to. The issue with The Downside With Jon Stewart is Jon Stewart himself.


Stewart’s very first brand-name visitor on his very first discuss present—The Jon Stewart Present on MTV, which premiered practically 30 years in the past on October 25, 1993—was the self-anointed “King of All Media” himself, Howard Stern. Stern, one in every of Stewart’s comedy mentors, was readily available to advertise his new memoir, Personal Elements, quickly to be a significant movement image additionally starring Howard Stern. And earlier than he even settled into the sofa, earlier than Stewart may get a phrase in, Stern instructed him that The Jon Stewart Present was going to get canceled, quickly, and that it could take Stewart’s profession down with it.

“I’m nervous about this present, I actually am,” Stern mentioned, commandeering the interview. “I wanna get the message out about my guide earlier than the present is canceled.” Then he addressed the viewers—Stewart’s viewers. “Does anyone know who Jon is and why I’m speaking to him?” This kind of factor is how comics present affection, however Stern additionally meant each phrase. “I used to be supplied a chat present on MTV, I’ll be trustworthy with you,” he mentioned, humblebragging earlier than there was a time period for it. “And I turned it down, and I’ll let you know why—they damage folks’s careers.”

“Nicely, Howard,” Stewart mentioned, lastly getting in a line. “I didn’t have a profession.”

Rewatching the primary few episodes, what stands out, moreover Stewart’s palpable terror and comically ill-fitting wardrobe, is a budding comedy icon looking for his topic. He had the nebbishy attraction of Woody Allen, minus the undercurrent of sexual predation. He was pleasant, media savvy (for 1993), and protected round your youngsters. Good for MTV. The giants of late-night tv—Carson, Letterman, Leno—didn’t come from this world. They weren’t outsiders. For Stewart’s amassing cult viewers, his outsiderness was the idea of the enchantment. What was this dork even doing right here? The optics had been subterranean, a secret late-night present working out of the basement of a late-night present, with a ripped Blues Traveler poster by the steps and a thumb-hockey board for a espresso desk.

Two torn pieces of a young and older Jon Stewart creating a singular portrait of him.
Illustration by Matthieu Bourel; Photographs by Peter Kramer / Getty; Motion Press

Stewart had discovered his place within the movie star caste system: the good aleck, uncool however cool-adjacent, thanks partially to a slate of legitimately hip musical friends, together with Ol’ Soiled Bastard and Dangerous Faith. Stewart’s vibe could have been Woody Allen, however his comedian hero was Carlin—the idol-smasher, the conscience of comedy, the impatient gives-no-fucks philosopher-king who took on the federal government, grasping firms, and Andrew Cube Clay for telling sexist, homophobic jokes, for punching down.

George Carlin was the place Jon Stewart was headed, however he couldn’t be that man on MTV. He needed to get canceled first.


Stern was proper, in fact, about all of it.

The Jon Stewart Present did get canceled, in lower than two years, and it did damage his profession, no less than for a short time. He acquired handed over for internet hosting jobs. He made the stoner comedy Half Baked together with his stand-up pal Dave Chappelle. He acquired stabbed within the eye by Josh Hartnett in The School. He acquired miscast within the ensemble love story Enjoying by Coronary heart as somebody who may ever, in his wildest goals, kiss Gillian Anderson. He had a recurring function on The Larry Sanders Present, Garry Shandling’s good, early-HBO late-night satire, as “Jon Stewart,” Larry’s understudy. For a short minute, based on an account by the comic and director Judd Apatow that seems in Chris Smith’s The Day by day Present (The E-book): An Oral Historical past, Shandling flirted with turning The Larry Sanders Present over to Stewart, however nothing got here of it.

Then, in 1998, the chief who’d employed Stewart at MTV, Doug Herzog, referred to as him a couple of job opening at a nascent cable community referred to as Comedy Central. Craig Kilborn, the fratty cocksure authentic host of The Day by day Present, had gotten his huge call-up from CBS to host the late-night slot following David Letterman’s, which was one in every of two jobs Stewart didn’t get. (The opposite was changing Letterman on NBC. That went to Conan O’Brien.) Stewart was within the Day by day Present gig, Smith stories in his guide, however provided that he may strip Kilborn’s model, which was humorous however typically mean-spirited, all the way down to the studs.

You already know the remaining.

And now, on April 24 on the Kennedy Middle, in Washington, D.C., Stewart will obtain the Mark Twain Prize for American Humor, which, apart from a collection order on HBO, is arguably comedy’s highest honor. In profession phrases, it’s the reverse of getting canceled. It’s canonization. He would be the Twain Prize’s twenty third recipient, becoming a member of a listing of luminaries that features Richard Pryor, Steve Martin, Lily Tomlin, Tina Fey, his beloved Carlin, and his buddy Chappelle, and that not consists of Invoice Cosby, whose honor was rescinded in 2018. “I’m actually honored to obtain this award,” Stewart mentioned in response to the announcement. “I’ve lengthy admired and been influenced by the work of Mark Twain, or, as he was identified by his given title, Samuel Leibowitz.” (Leibowitz is Stewart’s beginning title. It’s a Jewish joke and a nepotism joke. I requested an interview with Stewart for this story however he declined.)

The Twain Prize is a traditional double-edged sword. The checklist of winners is brief, and the names—to place it in comedy phrases—actually kill. As Joe Biden may say, it’s an enormous fucking deal. (You already know who doesn’t have a Twain Prize? Howard Stern. Except he turned that down too.) It additionally signifies that your finest work is behind you, and shortly you’ll want spectacles to see it. Nobody has ever adopted up a Twain Prize with their masterpiece, and Jon Stewart won’t be the primary. On this rely, Twain Prize winners aren’t any Mark Twain. Stewart spent the primary three a long time of his profession anticipating failure, assuming that tomorrow could be the day it’d all come crashing down, and as an alternative in some way he managed to exit on prime, on his personal phrases. No surprise he’s appeared misplaced ever since.

Stewart departed The Day by day Present in 2015 after a 16-year run that stretched throughout three presidencies; the hanging-chad election of 2000; 9/11; the Iraq Struggle; Hurricane Katrina; the election and reelection of Obama; the Nice Recession; the superior stupidness of the Tea Celebration; the capturing of Michael Brown in Ferguson, Missouri; and the rise of Donald Trump, or no less than his descent down that escalator when he introduced his candidacy for president. He was already inching away from the present that made him a celebrity by 2013, although, when he took a break to jot down and direct a film referred to as Rosewater, a considerate indie drama based mostly 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. Contemplating it was made by the host of a late-night present, Rosewater turned out admirably nicely, but it surely didn’t herald the arrival of a recent auteur. Additionally nobody went to see it. John Oliver stuffed in for Stewart throughout his sabbatical from The Day by day Present, and it was exhausting to not discover how rather more spry Oliver appeared behind his boss’s desk.

As soon as Trump arrived, Stewart all however vanished. He signed a four-year manufacturing take care of HBO that resulted in 2020 and produced actually nothing—4 years, nothing. There was an animated-shorts collection that by no means occurred. A brand new stand-up particular was introduced, then by no means spoken of once more. He tried making one other film, a political comedy he wrote and directed referred to as Irresistible, starring the Day by day Present alum Steve Carell and Bridesmaids’ Rose Byrne, about two rival marketing campaign strategists locking horns over a small-town mayor’s race, however the completed product feels just like the work of somebody who realized it was hopeless within the modifying room, and possibly even whereas he was capturing it.

Stewart was getting into the lifetime-achievement part of his profession, in different phrases, and possibly we shouldn’t roll our eyes so simply at solely being the voice of one technology. It’s straightforward to overlook now, however there was an inflection level when Comedy Central may’ve simply been the palace of Craig Kilborn and Tosh.0. Stewart dragged The Day by day Present—in opposition to its will, based on Smith’s oral historical past—in the other way, and he wound up giving Comedy Central its core identification, to not point out a rack of Emmys, together with a exceptional 10 straight for Excellent Selection Collection from 2003 to 2012. With out Stewart’s Day by day Present, there’s no Colbert Report, no Final Week Tonight With John Oliver, no Day by day Present With Trevor Noah. However possibly no Tucker Carlson Tonight, both.

Stewart may’ve pulled a Jay Leno and hung onto The Day by day Present eternally. As an alternative he had the unusual grace to see the tip coming, and to get out earlier than he’d overstayed his welcome. In his heyday, having a “senior Black correspondent” made for biting satire. By the tip of his run, it was time for a Black host. His trademark self-deprecation had drifted too removed from the truth of his station in life. The richer you get, the extra well-known you get, the more durable it’s to be the avatar of populism. His protestations that he had no actual energy, that he wasn’t a part of the institution, or the mainstream media, stopped ringing true. And for good motive. It’s exhausting to punch up from the stage of the Kennedy Middle.

Perhaps that’s what explains his second-act squishiness. After 4 misplaced years at HBO, Stewart signed a brand new deal in 2020 with Apple TV+ and swiftly introduced plans to get again to his roots: telling jokes about present occasions. His new collection, The Downside With Jon Stewart, would strike again in opposition to what Stewart has described because the arson economic system of social media with some room-temperature nuanced dialog. It sounded lots like The Day by day Present, solely longer and fewer humorous, and as an alternative of 4 episodes per week, Stewart was going to ship simply eight episodes per season. Every episode would observe a three-act format: opening monologue, professional roundtable, sit-down interview with somebody highly effective—the chair of the Securities and Alternate Fee, the Veteran Affairs secretary, the CEO of Shell. If The Day by day Present was a parody of a nightly information present, although, The Downside typically seems like a defanged Actual Time With Invoice Maher.

Stewart gave the impression to be retreating into protected territory, however so what? We are able to’t all be Bo Burnham, Svengali-ing stand-up specials for different comics, or an Oscar winner like Jordan Peele, or a film star like Steve Carell, or a sitcom legend like Tina Fey. George Carlin had one short-lived TV present (The George Carlin Present, which lasted 18 months on Fox within the mid-Nineteen Nineties), by no means directed a film, by no means did rather more than play himself in films, and nobody thinks his profession is incomplete. He was one of many voices of his technology too, and that was a lot.

However he additionally by no means phoned it in, not onstage anyway. The Downside With Jon Stewart is a strikingly unambitious, defiantly premature present that confuses thrift with substance, as if spending cash on something however workplace furnishings is an indication of mental unseriousness. Throughout his Day by day Present emeritus part, Stewart took some retroactive flak for the sausage fest in his writers’ room and for making an attempt to treatment the failure with token hires, and to his credit score, he copped to the criticism. Throughout a June 2020 interview on the radio present The Breakfast Membership, he recalled “going again into the writers’ room” after a vital article in Jezebel “and being like, ‘Do you imagine this shit? Kevin? Steve? Mike? Bob? Donald?’ Oh … Uh-oh. Uh-oh.” Now, on his Apple present, he appears to be hyperconscious of decreasing his white-male-celebrity footprint. The Downside With Jon Stewart is a multi-platform model, which is to say there’s additionally a podcast, a Twitter feed, and a YouTube channel, but it surely all feels just a little dutiful, and although Apple declared the present a direct hit with viewers, nicely, have you learnt any of them? Have you ever seen even a single viral clip from it?

“I’m having a tough time determining what you’re going for,” the New York Instances opinion author Kara Swisher instructed Stewart in her casually insulting method on a latest episode of her podcast Sway. She referred to as his Apple present “spare.” (“Once I say ‘spare,’” she mentioned, actually pouring it on, Howard Stern–type, “it’s spaaare.”) She dismissed the present’s opening quarter-hour because the “starting half, the place you do your Jon Stewart factor with an viewers.” Baffled, she posed the query to him as an alternative: “What do you assume you’re going for?”

“I at all times discover that query unusual,” he replied. Credit score to Stewart—he knew what he was entering into with Swisher and infrequently appeared to benefit from the roasts. “Do we’d like this? … There’s like 5 CSIs!” He’s not making an attempt to revolutionize tv for the second time. Like many middle-aged males blessed with the nice fortune to dwell out his days in cruise management, he’s simply making an attempt to make himself helpful. “I at all times discover the self-justifying facet of it just a little odd.”

Then he tried once more to truly reply her query: “If I believe noise is the antithesis of progress, [then] what if we tried to make one thing that was an equalizer? … That attempted to convey some readability to a loud dialog?” This didn’t transfer Swisher, who absolutely considers it her job to convey readability to a loud dialog. She pressed him on why he didn’t flip round a quick episode on Ukraine, settling as an alternative for a months-old rehash of the GameStop saga at a time when the world is going through the best menace of nuclear annihilation since possibly 1983. He responded by likening the media to “8-year-olds enjoying soccer,” a solution that’s about as intellectually rigorous as seeing one thing you don’t like and calling it “faux information” or “clickbait.”

“Not climbing on the second is a bonus, not a drawback, for the kinds of issues we need to discuss,” Stewart had insisted at one level within the dialog. If this simply seems like an excuse for complacency, Swisher appeared to assume so too. “I don’t imply to say ‘Has time handed you by?’ however …” she started, then trailed off, which drew an enormous cackle from Stewart.

“Sure, time passes all of us by,” he conceded. “I’m not going to faux that I’m not 60 subsequent 12 months.”

He was defending his Apple present as if it had been a comfy pair of Allbirds, the streaming equal of a Vegas residency. However the extra Swisher pressed, the extra wounds she revealed. The Trump period appeared to have rocked his religion in his former occupation. He used to imagine within the energy of comedy to carry politicians and billionaires to account, and in his personal energy to no less than make a dent. However he’s not so positive anymore. “It’s nice, it’s a distraction,” he mentioned, “however in the end feckless.”

For somebody about to win the Twain Prize, he sounded awfully defeated. He left The Day by day Present seven years in the past, and since then, he instructed Swisher, “virtually every part that I believed and advocated for didn’t come to move, and possibly acquired worse.”


As soon as upon a time, for those who accused Jon Stewart of really making an attempt to unravel issues, of making an attempt to contribute one thing extra helpful than dick jokes, he’d plead dumb comic—I’m simply right here to make folks snigger! It was insincere then, and now it’s being parroted by Joe Rogan to excuse spreading COVID lies all over the world. But once more Stewart’s ways have been weaponized by forces of disinformation. Stewart’s response, although, has been to drop the veil of comedy altogether. Apart from his Jon Stewart factor in the beginning of The Downside and some wry asides throughout interviews, he’s not even making an attempt to be humorous. Whenever you take the comedy out of topical comedy, although, you turn out to be … the media. (“I believe you’re a great comic. I believe your lectures are boring … I do assume you’re extra enjoyable in your present,” Carlson mentioned to Stewart in that Crossfire look, all these years in the past. For as soon as, Tucker was telling the reality.)

And as The Downside With Jon Stewart makes clear, humorous one-liners and five-minute chats with pliant celebrities aren’t significantly good follow for roundtable conversations with coverage consultants and prolonged interrogations of polished CEOs. An early episode that described the U.S. armed providers’ continued use of poisonous burn pits close to army 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 damaged system, and blaming it on the man who was mere months into the job and was patiently making an attempt to clarify the obstacles in his path. If Stewart’s aim was to make his viewers really feel sympathy for a federal bureaucrat, he nailed it.

Greater than as soon as already, Stewart has devoted a complete episode to a topic, solely to have an precise professional on that topic name him out for getting it unsuitable. The primary time, a Wall Road Journal editor took exception to the mess Stewart made making an attempt to summarize the GameStop saga—and, severely, go watch the episode if you wish to perceive it lower than earlier than you watched—and to his portrayal of Redditors as folks heroes education the elites. Days later, Stewart acquired 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 metallic recycling work nice) and for going too straightforward on oil corporations.

As a result of that is 2022, Stewart responded by inviting each reporters onto his podcast to hash it out some extra. He appeared to bridle in opposition to the Journal editor’s suggestion that he was being naive about GameStop, so he doubled down, ranted concerning the want for extra transparency round extraordinarily non-public monetary transactions, then did the Tucker Carlson factor the place he accused the journalist of being the naive one. No less than with the local weather reporter, Stewart conceded his errors and wound up having the sort of detailed, enlightening dialog that it positive would’ve been good to see on his new tv present.

If Tucker Carlson is what you get once you detach fact from actuality, The Downside With Jon Stewart is what occurs once you don’t sew them again collectively nicely sufficient. You may pollute conversations with the perfect of intentions. You may mislead thousands and thousands of individuals whilst you’re making an attempt to convey some readability to the dialog. Simply ask Joe Rogan. Even Stewart doesn’t use that dumb-comedian line anymore. He is aware of he must do his Jon Stewart factor with a view to get our consideration, however he doesn’t have a lot religion in his personal shtick anymore in opposition to the likes of Donald Trump and Tucker Carlson. He could have received the Twain Prize, however go ask Jon Stewart who he thinks received the battle.



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