It seems oddly fitting that the second season of Apple TV+’s The Problem with Jon Stewart premiered the week of Yom Kippur. Because the host spent his first episode back after an extended break atoning for his—and by extension, the rest of the comedy community’s—history of making jokes at the expense of trans people.
The episode, titled The War Over Gender, opens with a classic Daily Show-esque montage of conservative commentators melting down over a new emoji of a pregnant man. But just minutes in, Jon Stewart offers up some self-reflection.
“We are in a new dawn of gender and sex complexity, where those who don’t fit in a simple binary are meant to be seen with humanity,” he says. “It wasn’t always like this, people. As recently as, let’s say, the 1990s, early 2000s, people were making shitty, reductive jokes about the subject.”
Stewart laughs uncomfortably as a decades-old photo of himself on The Daily Show appeared on screen beside him. “What can I say, the joke rhymed,” he adds. “Shitty and reductive jokes are kind of my brand.”
From there, the host moves on to more modern examples of the “vicious backlash” to this new moment of “progressive visibility” and notably does not include any video evidence of his past transgressions.
A change.org petition from 2013 calling on both Stewart and his Comedy Central partner Stephen Colbert to “reject transphobia” on their respective shows cites a couple of examples. They include Stewart joking that he “accidentally picked up a tranny hooker at a truck stop” and another bit that features an ugly description of a so-called “transvestite.”
So as cathartic as it is during the new episode to watch him challenge the ignorant arguments of conservative pundits like Ben Shapiro—and Arkansas Attorney General Leslie Rutledge, whom he speaks to directly in a devastating interview—Stewart knows that he is hardly seen as an authority on the issue. That’s why he also brings in an endocrinologist, two parents of trans children, and Chase Strangio, a trans attorney with the ACLU, to help him understand what the anti-trans movement is getting so wrong.
The simple fact that Stewart decided to dedicate his show’s Season 2 premiere to the topic—and acknowledge that he has historically been part of the problem—is commendable. And it stands in sharp contrast to his good friend Dave Chappelle, who has only doubled down on his anti-trans material since first coming under fire for targeting that community in his 2021 Netflix special The Closer.
Amid the controversy surrounding Chappelle last fall, Stewart openly defended the comedian as a “good” and “decent” man who did not intend to hurt anyone with his words. “I know his intention is never hurtful,” Stewart said at the time. “He’s just not that kind of person.”
One can argue whether or not Chappelle’s intention should even matter in that case, but Stewart’s objective and the impact of his new episode are fairly clear. By rejecting his own transphobia and actively educating himself on the topic, he is demonstrating that stubbornly refusing to evolve in the name of “free speech” is not the only answer.
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