How Jon Stewart Went From Liberal Hero To Problematic Pariah

NEW YORK, NY - AUGUST 9 : Comedian Jon Stewart, host of Comedy Central's The Daily Show, works in his office on August 9, 2011 in New York. (Photo by Benjamin Lowy/Getty Images)
Benjamin Lowy/Getty Images

Jon Stewart never should have left the public stage.

The liberal comedian famously quit Comedy Central’s “Daily Show” in 2015, shocking progressives who couldn’t live without him “destroying” some GOP target five nights a week.

The left and the media (repetitive, I know) went into a lengthy period of mourning following his departure.

Slowly, a new crop of Stewart types took his place. These comics made even less of an attempt to be fair and balanced. They were meaner, too, leaning into Stewart’s bleep-filled rants with a venom Stewart rarely brought to his Comedy Central perch.

One example? Samantha Bee kicked off her TBS hate-fest “Full Frontal” by calling Sen. Ted Cruz a “fist-faced horse-s*** salesman.”

It only got more “feckless” from there.

Meanwhile, Stewart tried to go the auteur route. He directed two films which made nary a ripple in the pop culture waters. His 2014 movie “Rosewater,” about a BBC journalist tortured by Iran’s Revolutionary Guard, earned respectable reviews but didn’t make an awards season splash.

His 2020 effort, “Irresistible,” did far worse. The amiable comedy, with just a dollop of partisan rage, dared to poke fun at both sides of the political aisle. Stewart might as well have donned a red MAGA hat in public.

Liberal film scribes didn’t want a fair and balanced satire. They wanted “Orange Man Bad: The Movie.” Stewart didn’t deliver it, and they let him have it.

  • “Irresistible isn’t just shockingly ineffectual in its insights into national schisms — it is, in an added betrayal, unfunny, requiring its audience to slog their way through so much laborious farce without a laugh in sight.” – Vulture
  • “Jon Stewart Returns with a Toothless Political Satire Out of Touch with Trump Era.” – IndieWire
  • “In desperate need of ruthless incisiveness, it goes soft at every turn” – Daily Beast

What Stewart couldn’t realize was how culture had lapped his brand of liberalism during his absence. 

Black Lives Matter. Antifa. AOC. Identity Politics. Woke, Inc.

More importantly, any attempt to lure right-of-center viewers into the conversation was considered a nod to White Supremacy.

Suddenly, Stewart was older … and old news.

The hard Left loved their new darlings, from Bee to Stephen Colbert. They had no time for a white cis-gender male who leaned on fellow white males in the writer’s room back in his day. 

His “problematic” past quickly began to haunt him during his hiatus.

Sure, his “Daily Show” run fueled the careers of John Oliver, Steve Carell, Ed Helms and Bee, but they were all the same skin color. His tenure also featured a blazingly white creative team, which caught the attention of radio’s “The Breakfast Club” last year.

Stewart said he became aware of the problem during his celebrated “Daily Show” run, but his attempt to fix it by removing the names from potential hires fell flat.

“But we still kept just hiring white dudes. White dudes from a certain background,” he said. “What we realized is the river that we were getting the material from, the tributary was also polluted by the same inertia. And you had to say to them, send me women, send me black people. And all of a sudden, women got funny. It just kind of happened. But they’d been funny all along. We just hadn’t actively done enough to mine that.”

The host also famously dueled with a rare black writer on his staff, Wyatt Cenac. Their confrontation would have gotten Stewart fired had it happened today.

Cenac complained that Stewart’s Herman Cain impression sounded racist, and he told his boss as much. Stewart proceeded to curse Cenac out, only later realizing the error of his ways.

“Those were hard lessons for me, and they were humbling lessons. And I was defensive about them and still didn’t do it all right,” he said later, hoping to smooth things over.


Never apologize to the woke mob. Stewart should know better than that. But he did it, and now that “on his heels” posture is coming back to haunt him.

Stewart announced last year that he’s ending his self-imposed TV sabbatical. His upcoming Apple TV show, “The Problem with Jon Stewart,” will examine a single, searing issue with every episode.

We’re learning more about the show of late, including some behind-the-scenes hires and the debut frame – later this Fall.

Along comes Vice to say there’s a “problem” with Stewart’s upcoming “Problem.”

The article leverages Cenac, again, who fears the show may be too similar to his own short-lived show, “Problem Areas.”

[Cenac] 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

That’s the nasty appetizer to Vice’s main course.

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? 

The article then cites Stewart’s take down interviews with the likes of Tucker Carlson and Jim Cramer, moments that felt good at the time but left no permanent marks. Each rose to greater media heights since then, and Vice suggests Stewart is partially to blame.

Yes, when the woke Left turns on you … anything goes.

The far-left AV Club has concerns about the new show, too.

Apple, obviously, is banking on Stewart’s continued appeal, but there’s a clear question at play here: Is that love still actually operative? The Trump era, which Stewart mostly sat out, was exceedingly hard on the idea that political satire, in and of itself, had the ability to effect real-world change—once a core part of the Daily Show appeal. Is Stewart’s particular, and once-potent, blend of sharp comedy, moral outrage, and intentional absurdity still in demand?

What’s missing from Stewart’s comeback story? The fact that HBO teamed with him a couple of months after he left Comedy Central for a four-year deal that included a slate of projects, including stand-up specials and an animated series.

Nothing materialized.

Maybe Stewarts’ hard-left critics have a point.

The views expressed in this opinion piece are the author’s own and do not necessarily represent those of The Daily Wire.

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