Jon Stewart still has some soul-searching to do. His first RNC show proved it.

Stewart interviewed his longtime interlocutor, frenemy and sparring partner Bill O’Reilly, but failed to address the most important question of all.

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Jon Stewart and “The Daily Show” on Tuesday executed what Deadline.com called a “Milwaukee pivot” — a programming change forced upon them by last weekend’s tragic violence in Butler, Pennsylvania. Originally, the idea was to air the popular fake news show live from the site of the Republican National Convention. The attempted assassination of Donald Trump, Stewart revealed, scuttled the plan. His Milwaukee venue was placed under lockdown. With “cages built around the theater,” Stewart and his team decided that it wouldn’t be prudent to perform live comedy “without,” the host deadpanned, “people.” 

What exactly are entertainers as influential as Jon Stewart supposed to be doing at a point in American history as troubling as this one?

Taped on Tuesday, the episode was stuck rehashing RNC highlights from Monday. Stewart thus missed an opportunity to skewer the speeches of former Trump detractors Nikki Haley, Ron DeSantis and Marco Rubio. Each performed variations, albeit less deserving of our enduring awe, of JD Vance’s ability to forget he once called his new boss “America’s Hitler” and “cultural heroin.” (Vance’s opioid analogy must be the most remarkable observation I’ve ever read about Trump). 

Stewart also interviewed his longtime interlocutor, frenemy and sparring partner Bill O’Reilly, and quipped about the two of them being “somewhat fossilized practitioners of the rhetorical arts.” In relation to their past popularity and influence on this generation of political rabble-rousers, Stewart observed, “We made a pretty spectacular living pushing those envelopes.”

This isn’t the first time Stewart has wondered aloud whether he is predator or prey (or peripheral) in the new social media ecosystem. In February he called himself “the captain of this dying medium.” He does seem to intuit that what worked artistically, and maybe even politically, in the Bush and Obama eras is perhaps outdated or irrelevant or actually not entirely helpful in this MAGA moment. 

If Stewart is pondering that, then good on him. I guess the venue change, and the terror that prompted it, should compel him to pose hard questions about the intersection between art and politics. Questions like: What exactly are entertainers as influential as Jon Stewart supposed to be doing at a point in American history as troubling as this one?

I’m starting to believe that Stewart and his team actually don’t know how to answer this question. No disgrace in that. I don’t either. The current moment is as baffling as it is frightening. Although, when your theater is caged in and your audience can’t attend for their own safety because yet another young white male tried to murder people with a perfectly legal killing machine — then, well, maybe it’s a good time to reflect.  

Tuesday night’s program indicated that the usually self-aware Stewart is still thinking this through, and has not yet made any discernible pivot. His jokes about odd noises made by Marjorie Taylor Green were funny enough. The analysis of how Lee Greenwood refused to cede the stage while introducing Trump was fairly hysterical. Trump himself gestured that the long-winded singer-songwriter should move this along (“Is it possible to bring out another band to play a band off?” Stewart quipped).

The Bill O’Reilly interview best encapsulated many of these contradictions that Stewart has to confront. These men, by my count, have interviewed each other some two dozen times over the years. They have excellent chemistry. They like each other. (Or, perhaps, they like to hate each other.) O’Reilly even recently attended Stewart’s show. The hard-charging conservative “newsman,” who was fired by Fox News in the wake of five sexual harassment suits (which he has denied), is sort of avuncular when conversing with Stewart.

O’Reilly made reasonable points about rage and today’s politics. “We are now in a society,” he opined “where hatred is rewarded.” Stewart jumped in: “It’s incentivized, it’s monetized!” Dialogue. Consensus. I like it!

One problem, though, is that the same O’Reilly who was bemoaning “the hate brigade” Tuesday night has been eminently hateful himself. I am not going to rehash his views on Trayvon Martin’s murder, on gay marriage, victim blaming, comparing the ACLU to terrorists, blatant and pervasive sexism, anti-LGBTQ and transgender rants, religious fearmongering (such as his yearly diatribe against the “war on Christmas”), or his discomforting white power vibes

I am going to say that Jon Stewart has to figure something out. When he’s choppin’ it up with Bill O’Reilly is he: a) fostering open and honest discussion across the ideological divide, thereby enriching our liberal democracy? Or, b) platforming a voice that is both cause and effect of the lethal danger that is threatening the existence of liberal democracy itself? Because it sure as hell can’t be both. 

When O’Reilly started reading off unflattering statistics about Biden’s economy, Stewart did push back, literally. He prompted his guest to explain how Biden is solely responsible for high food prices, gas prices, mortgage rates, etc., given what he inherited from his predecessor. When O’Reilly responded he didn’t know, Stewart guffawed, comically pushed back his own chair, got up and walked away. 

An interesting gesture, that was. No one is asking Stewart to walk away from his comedic throne. But I’d hope the events of the past few months might stimulate deeper reflection on what artists are supposed to do in dark times.

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