The Problem With ‘The Problem With Jon Stewart’

Can the beloved former host of ‘The Daily Show’ be relevant in 2021 without copying the work of his former staff?
Chicago, US
Jon Stewart
Comedian and activist Jon Stewart, center, speaks during a news conference at the U.S. Capitol in Washington, D.C., U.S. on Tuesday, Sept. 15, 2020. Photographer: Stefani Reynolds/Bloomberg via Getty Images

Jon Stewart ended his 16-year-run as host of The Daily Show exhausted. When he announced he'd be leaving in 2015, he said, "This show doesn’t deserve an even slightly restless host, and neither do you." So it's no surprise he's spent much of the almost six years since his last Daily Show broadcast out of the spotlight, only showing up for sporadic chummy interviews on his former protége's Late Show with Stephen Colbert, testifying to Congress in 2019 on healthcare for 9/11 first responders (a cause he's championed for decades), and directing a 2020 feature film called Irresistible, a political satire with a 40 percent Critic score on Rotten Tomatoes.


But Stewart's television absence will be ending this fall, when Apple TV+ debuts his new series, The Problem With Jon Stewart—offering the once-ubiquitous host an opportunity to figure out where his distinctly snarky brand of political comedy fits in a post-Trump and pandemic-stricken America. 

The show is billed as "a multiple season, one-hour, single-issue series” combining serious investigations into political topics with talk-show comedy. If you think this sounds like the premise of a number of shows from former Daily Show contributors—think: Last Week Tonight with John Oliver, Patriot Act with Hasan Minhaj, and Problem Areas with Wyatt Cenac—you're not wrong. In fact, Cenac, who hosted Problem Areas between 2018 to 2019, when HBO canceled it, tweeted his displeasure with the undeniable similarities between the two programs. He posted a clip of a monologue he'd delivered on Problem Areas: "But if there's one thing I've learned: If you want somebody to take a Black guy saying something meaningful on TV seriously, you really need to have a white guy saying basically the same thing right after," he'd said

Cenac worked with Stewart as a Daily Show correspondent from 2008 to 2012, and was the only Black writer on staff. In 2011, Stewart did an impression of then-Republican presidential candidate Herman Cain that many, including Cenac, found racially insensitive. On a 2014 appearance on WTF with Marc Maron, Cenac recalled confronting Stewart about it. "[Stewart] got incredibly defensive," Cenac said, mentioning that he told the host the impression bothered him and sounded like Kingfish from Amos 'N Andy. "And then he got upset," Cenac remembered. "And he stood up and he was just like, 'Fuck off. I’m done with you.' And he just started screaming that to me. And he screamed it a few times. And he stormed out. And I didn’t know if I had been fired."


Cenac said that Stewart "kind of apologized as much as he could" in private, but that "I felt hurt.” On a 2020 Breakfast Club appearance, Stewart admitted that his dust-ups with Cenac "were hard lessons for me, and they were humbling lessons." He added: "I was defensive about them and still didn’t do it all right.”

In that same Breakfast Club interview, Stewart also apologized for the lack of diversity on his Daily Show staff. He told the story of how he reacted to a 2010 Jezebel article that called the show a "boys’ club where women's contributions are often ignored and dismissed." After he read it, he said, he responded by “going back into the writer’s room and being like, ‘Do you believe this shit? Kevin? Steve? Mike? Bob? Donald?’ Oh…Uh oh. Uh oh.” 

The Problem does promise to fix some of The Daily Show's past mistakes: For one, he's hired women in key roles, including CBS Evening News veteran Brinda Adhikari as his showrunner and Daily Show alum Chelsea Devantez as his head writer. On top of that, the show's producers, showrunners, and Stewart are apparently poring over 2,400 writer's packet submissions to round out their staff. 


Even if Stewart prioritizes diversity in his hiring practices, there's still the question of where he fits in in the political and entertainment landscapes of 2021. With former Daily Show correspondents like Samantha Bee, Oliver, and Minhaj now helming similar shows of their own, and Trevor Noah's very capable tenure as Daily Show host who's able to speak about race and injustice in more resonant ways than his predecessor, how will Stewart set himself apart? 

When Stewart was at his best, he would humorously break hot-button issues down into digestible packages, often with striking moral clarity. But how he'll be able to speak truth to power in 2021—a year when America is still in the throes of COVID-19, an enraged Trump-loving right-wing, and rampant racial inequality—on a streaming platform like Apple TV+ is a big question mark, especially when so many of his protégés have already done it well—with attention to the nuances of issues like diversity and feminism where he has previously faltered in his own writers’ room. Stewart's absence during the Trump years wasn't exactly missed, because liberals had bigger things to worry about than receiving welcome confirmation bias for 30-minutes on Comedy Central. 

Some of Stewart's best moments on the Daily Show were his adversarial interviews with and takedowns of conservative blowhards. His 2004 Crossfire appearance, where he excoriated hosts Tucker Carlson and Paul Begala for exacerbating partisan polarization and prioritizing outrage over substance effectively ended the CNN show, but it certainly didn't end Carlson's career. Since then, Carlson has become the top-rated cable host and on Fox News, doubled down on his worst impulses, and used his platform to defend the Capitol insurrection, "white replacement theory," and Qanon. Stewart's 2009 takedown interview with CNBC hack Jim Cramer in the wake of the financial crisis was great and righteous, but Cramer is still the host of Mad Money on CNBC. And Stewart's 2010 Rally to Restore Sanity And/Or Fear in response to right-wing disinformation didn't do much but give liberals smug satisfaction. It did not anticipate the rise of Donald Trump—or, as Stewart called him in 2013, "Fuckface Von Clownstick"—or how much worse things would get. 

In a 2020 interview with the New York Times promoting his Irresistible, Stewart likened returning to the spotlight during such a tumultuous year to "showing up to a plane crash with a chocolate bar." "There’s tragedy everywhere," he said, "and you’re like, ‘‘Uh, does anybody want chocolate?’’ It feels ridiculous. But what doesn’t feel ridiculous is to continue to fight for nuance and precision and solutions." That optimism—resting on an unwavering belief in practical, good-faith politics—has been Stewart's operating principle for his entire career. It's an instinct that's inspired him to champion causes like the 9/11 Victim Compensation Fund and lambast corrupt politicians and pundits. It spurred him to bring awareness to partisan gridlock and corruption to an audience who came for jokes while inspiring and employing a new generation of talent. But if The Problem With Jon Stewart can't find its voice for this distinctly dystopian moment, that track-record might not be enough for it to stand on. 

A previous version of this article stated that Wyatt Cenac hosted Problem Areas from 2016 to 2018. He hosted from 2018 to 2019. We regret the error.