In September, Jon Stewart will make his comeback, again, with a new show on Apple TV+ called The Problem With Jon Stewart. But one of the problems with Jon Stewart is that his widely beloved former show existed in a time when most media marched in sneering lockstep with the political establishment (see: Miller, Judy), when the presence of even a tepid voice calling out that self-evident dissonance seemed radical, fresh, and riveting. This time ended just after Stewart’s show did, leaving the now 58-year-old TV host with an arguably undeserved halo of renegade comedy coverage that he’s threatening now to totally fuck up.
In the seven years since Stewart retired from The Daily Show, an entire administration has come and gone, and with it the comfortable closeness between the pundits he used to mock and the politicians they covered. It’s not that media is any less self-important — it may possibly be more — but the Trump era positioned so many websites and late-night programs in pretentious opposition to his flagrantly offensive agenda (a perfect piece on this here), that it minted a series of faux-martyr mini-Stewarts, which his new show will probably join if at all resembles Stewart’s recent activity. Per Bloomberg:
In 2015, Stewart signed a four-year deal with HBO. But his first show, billed as an “animated parody of a cable news network,” died in development. Last summer, Stewart directed Irresistible, a political satire starring Steve Carell, which premiered in the aftermath of George Floyd’s death during a fiercely contested presidential campaign amid a global pandemic. Stewart described the timing to the New York Times as “like showing up to a plane crash with a chocolate bar.” The film got mixed reviews.
And at least in format, Stewart’s new project already seems to borrow from the existing repertoire. “Each hourlong episode, according to Apple,” Bloomberg writes, “will dig into a single issue — an approach that’s similar to the HBO program hosted by John Oliver, Stewart’s old colleague.” This seems promising:
On July 20, the day Amazon.com Inc. founder Jeff Bezos took a brief trip to space, Stewart posted a three-minute mock movie trailer on Twitter, giving a taste of what his show may look like. Bezos, played by Jason Alexander of Seinfeld fame, goes to space in a rocket shaped like a penis. There, he clashes with other phallic space vehicles staffed by rival billionaires Elon Musk (Adam Pally) and Richard Branson, who was played by a mop.
On the plus side, Stewart’s weekly hour will air just as thousands of Apple TV+ free trials end, so it may be that no one hears much about his problems at all. Or perhaps Stewart has actually waited just long enough and the Biden-era will signal a return to the cushy, toothless coverage of the Obama years, where his insights will seem revelatory. He wouldn’t be the first figure to reboot an aughts media brand a decade after the fact and imperil whatever fuzzy goodwill people have harbored over the years. We wish him the best.
An earlier version of this piece said this show would air on “Apple+” — it is actually “Apple TV+”. Sorry about that.