The Problem With Jon Stewart And ‘The Daily Show’ Reunion Hopes And Dreams

Yes, Jon Stewart is suddenly in need of a platform, and The Daily Show has yet to land on a permanent host. But while those circumstances –- born from The Problem With… Jon Stewart getting cancelled reportedly after he refused to bend on creative control with Apple over stories on AI and China –- line up nice, I can’t imagine Stewart returning to the chair he held for 16 years… with one possible exception.

Let’s remember a few things about Stewart’s previous exit and his moves since. First and foremost, a daily show is a very different animal than a bi-weekly or weekly one. Notice all the Daily Show-esque shows that sprung up since Stewart left and how they have all gone toward the weekly model (most have also died, but that’s not the point, though it is a point). It’s not just about the endurance required to put on a show night after night. It’s about being able to do it in a way that stands out in the very crowded media and political comedy space and being able to sustain that.

The reason The Daily Show has been able to do that is because they have an amazing team of writers and a legendary crew of correspondents. Ronny Chieng, Desi Lydic, Jordan Klepper, Roy Wood Jr. (before his recent departure), Dulce Sloan, Michael Kosta. Each could reasonably carry their own show. Some really need to. But to do the kind of show Stewart pivoted to, with deeper cuts and a harder news focus, it’s just not possible on a nightly basis no matter the talent. You’d run out of money, angles, and energy pretty quickly.

“So why doesn’t Stewart just do the show he used to do” First, while attitudes shift and nostalgia blooms, it’s been a very long time since Stewart’s exit and he didn’t seem like he was getting the same level of fulfillment from the job that he had previously. From a 2015 interview with The Guardian:

“It’s not like I thought the show wasn’t working any more, or that I didn’t know how to do it. It was more, ‘Yup, it’s working. But I’m not getting the same satisfaction. […] These things are cyclical. You have moments of dissatisfaction, and then you come out of it and it’s OK. But the cycles become longer and maybe more entrenched, and that’s when you realize, ‘OK, I’m on the back side of it now.’”

Second, Stewart had every opportunity to do any show he wanted to (just ask HBO) and he chose the style and format of The Problem With. If he didn’t want to keep doing The Daily Show back in 2015 or even a direct copy in 2021, why would he want to now The fun atmosphere of the world at large

Listen, I know it’s instinctual to say everything is worse and more complicated now vs the halcyon days of yore. But shit is objectively worse right now than when Stewart left.

We’re literally living in the scene from John Carpenter’s The Thing where Kurt Russell’s muses into a tape deck that nobody trusts anybody and that they’re all tired after a series of events where dogs and friends get taken over by some kind of parasitic creature that’s trying to learn us so it can replac… oh shit, I just described AI! Don’t tell Apple.

Why would Jon Stewart want to take a nightly tour of the depressing cycles of poverty, injustice, and hate in this country and all over the globe Why would he want to cover daily Trump indictment updates, the DNC Presents: Weekend At Biden’s, outrage theater, conspiracies conspiracies everywhere, and two complex and brutal wars That’s not even counting the “civil” one going on in the U.S. over guns and the real societal danger: books and drag performers. While there’s value in illuminating the crushing boulders that fall off bullshit mountain and in guiding us through the news, it’s not absolute or lasting value. Not when our attention spans are…

The Exception With Jon Stewart

I don’t think this will happen for the reasons stated above and because it’s just too clean and storybook. But… This whole speaker of the house thing has me thinking. No Daily Show guest host has been able to secure the votes to get elected perma-host. What if Jon Stewart became a temporary babysitter

Maybe an instant, short(er) term fit where he slides back into his old gig holds appeal; some kind of hybridized cross between what The Problem With was and what The Daily Show is (because, The Daily Show is still really good, even sans host, which is a credit to showrunner Jen Flanz and the existing staff). Maybe he can even take us through the election… and whatever immediately follows (he said with fear and utter exhaustion).

Returning to The Daily Show could be exceptionally lucrative for Stewart immediately and in the future (though, it’s not like he’s going to begging for pennies after leaving Apple). It would also cut through the competition and put The Daily Show at the center of what may be (and stop me if you’ve heard this one but also it’s really true) the most consequential election in the history of this wacky country. Especially since Jon missed out on all the fun in 2016 and 2020. And what fun there was (he said with even more exhaustion).

Seriously, I don’t subscribe to this thinking, but some people feel like Stewart left business unfinished at the start of the Trump era. This is ludicrous because as much as we love and appreciate these shows, it’s not like having Jon Stewart in that chair would have had a substantial effect on those elections or on the way the country was run. The days of The Daily Show scaring powerful people are long gone, not because of a deficiency with the show but because of a shellshocked audience and news cycle that only knows maximum speed. Also, irony and satire died a few years ago, and the consequences of hypocrisy haven’t been seen more than a slap on the wrist in a long time.

With all that said, Stewart does have an unmistakeable value. He’s the security blanket of political comics, making us feel a little better, a little smarter, and a little safer when he was adding context to the issues of the moment. I bet a lot of people would celebrate the chance to feel that way again, even if it was probably a product of less chaotic times.

For Stewart, I suppose going back might represent some kind of Groundhog Day scenario of a repeating nightmare absent Andie McDowell and all you can eat breakfast food. Or maybe it’s the greatest challenge of his career and a totally thankless task (aside from the money)! It would be one of those things, definitely… maybe.

On second thought, maybe he should just run for President. Might be easier.