Jon Stewart's Descent Into Mediocrity

A twenty year legacy goes down in flames in as many minutes.

Jon Stewart pictured center-right, next to Andrew Sullivan.

Jon Stewart appeared on my radar last week. Since retiring from The Daily Show in 2015 (though it feels longer), Stewart faded from the public eye, a fondly remembered cultural staple from Millennials’ adolescence and young adulthood. I never quite adored him in the way so many others of my generation did, but he had my respect. While their politics differed somewhat, I always thought of Jon Stewart as the poor man’s Bill Maher. More acceptable. More dumbed-down. Funny, though a little bland for my taste. But, like Maher, he was always someone you could count on to call bullshit, to tell it like he saw it, even for his own side, in as unfiltered a way as the FCC would allow. He wasn’t just another party hack or partisan bimbo. He was a voice of reason, one I greatly admired for over two decades. No longer.

Last week, Stewart resurfaced on my Twitter feed, not because people were sharing old clips, but as part of his new Apple talk show, aptly named The Problem with Jon Stewart, whose first season was just wrapping up. Its finale was an episode on race in America. The Stewart I remembered from the Bush and Obama era was gone. In his place was a man who appeared as though he had spent the intervening years serving as president, because he had certainly aged like one. I watched this little gray man’s mouth work as though ventriloquized by race entrepreneurs Robin DiAngelo and Ibram X. Kendi. The first segment I encountered was called “The Problem With White People”, which collapsed all nuance and erased every trace of agency from black Americans, reducing them to the role of billiard balls mindlessly knocked around the pool table of society by the cues of white supremacy. And by white supremacy, of course we mean white people.

The next segment was an all-white in-person panel discussion led by Stewart, with abashed Yale sociology professor Chip Gallagher, and Lisa Bond, who runs a white-shaming group called Race2Dinner, which she seems never to lose. Appearing via Zoom for his kangaroo court hearing was conservative writer Andrew Sullivan, brought on to be the right-of-center Alan Colmes, a punching bag for the “other side”, and a scapegoat for all that is evil in society. Awkwardly omitted was the fact that Sullivan, the “resident white racist”, voted for Barack Obama twice, for Clinton in 2016, and for Biden in 2020. Nor the fact that he has been a tireless critic of the problems on his own side, a virtue Stewart has forgotten in his pandering dotage. No mention was made of the instrumental role Sullivan played in advancing gay marriage, a cause he began championing in the 1980’s as a conservative. True, the episode wasn’t about gay rights, but it’s one of the things Sullivan is most known for. Here’s an inconvenient truth: Andrew Sullivan has done more to advance human rights in his lifetime than Jon Stewart. More than everyone in that entire building during the filming of that farce.

Over the course of 20 minutes, what transpired can only be described as a struggle session. Sullivan — who said he had been invited on the show at the last minute under the pretext that it would be a one-on-one interview with Stewart rather than a three-on-one brawl — was cursed at, name-called, ridiculed, cut off, and talked over. All while a live audience of jeering woke parishioners roaringly applauded every point made by anyone other than him. Sullivan had not believed, going in, that a person of Stewart’s standing could be capable of such a reputation-nuking display of far-left dishonesty. I could hardly believe what I was seeing either. I have never lost so much respect for a person in the span of a few minutes as I did for Jon Stewart watching those clips.

Regardless of his excuses, it was not Sullivan’s finest showing. Sure, he was bamboozled and ambushed, but his points were inelegantly made. He seemed to dither as he spoke, squirming uncomfortably in his seat. For a person who has been a public figure for almost as long as I’ve been alive, who’s done probably hundreds of interviews and media hits, many of which have been contentious and adversarial, his performance was decidedly lackluster, even under the circumstances.

Looking back, it strikes me that many of the old Daily Show alumni have followed similar trajectories. Stephen Colbert went from a master of witty satire to an anodyne blue-state #Resistance mascot whose jokes now evoke approving “clapter” more than genuine laughter. John Oliver transitioned to reading “Now This” segments off of a teleprompter with one-liners inserted every 25 seconds. Oliver’s Last Week Tonight is like fish sticks for your mind: You enjoy it as a young person, lose your taste for it as your brain finishes developing, then years later look back mystified that you ever put that trash in your body. Only Lewis Black has evaded this backslide into insanity, which is ironic, given that he’s made an entire career out of playing a borderline maniac on the verge of snapping.

It speaks volumes about a person to witness the ways in which they change with the currents of the time. Some people never budge an inch, and the world passes them by. Others adapt to every chic du jour like a chameleon. Your views are supposed to change over time as new information arises. What’s not supposed to upend itself are your values and principles. Jon Stewart used to be the kind of principled liberal who valued calling out excesses and nonsense wherever they were. Now he’s become just another left wing partisan whose only critique of his own side is when they don’t go far enough to the extreme. Whether he, and so many like him, have done so in a bid to stay relevant, or because they’ve drank the Kool-Aid, I can’t say. I’m not sure one is less embarrassing than the other.

See also: “The Critical Race Theory Debate is Dripping In Bullshit”

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