Jon Stewart targets billionaire space race in first Apple TV Plus show promo
After lambasting Bezos, Musk and Branson, we learn “The Problem With Jon Stewart” is coming out in September.

Credit to Jon Stewart, it’s clear he was ahead of everybody on the joke that the rocket Jeff Bezos used for his Blue Origin space flight on July 20 looked like the male appendage, as we see in the first promo for the former The Daily Show host’s new Apple TV Plus series, The Problem With Jon Stewart.
Stewart tweeted a trailer that not only takes aim at Bezos, but Elon Musk and Richard Branson, depicting the three billionaires and their obsession with going to space as little more than a way to stroke their (ahem) egos.
Jason Alexander plays Bezos, Adam Pally plays Elon Musk, while Richard Branson is depicted by a mop and a stray cat shows up as a stand in for Facebook CEO Mark Zuckerberg. Tracy Morgan also appears as, per the promo, the “diverse friend who would never actually hang out with Jeff Bezos.”
Stewart does not make an actual appearance in the trailer, with the only indication that it is even for his show coming in the form of text over a black screen saying that it will debut in September; previously we had only known it would arrive on Apple TV Plus sometime in the fall.
Sorry for the aborted launch!!! I’m a bad twitterer. Enjoy this small step for man! pic.twitter.com/6gBHHJLByQJuly 20, 2021
While the style of humor is definitely reminiscent of the topical attacks Stewart made famous during his time as host of The Daily Show (with a much larger canvas), it was a bit disappointing that it didn’t offer a clearer picture of what The Problem With Jon Stewart is going to be like when it does premiere.
The description of the show that Apple released in April bills it as a one-hour, single-issue series that will explore topics that are part of the national conversation and Stewart’s advocacy work. There will also be a companion podcast to the series. Will it use skits like what the promo shows, or be something more akin to what Stewart did on The Daily Show? We still don’t know. Nevertheless, it is exciting that Stewart will make his first full-time stint on TV (or streaming, if we want to be technical) since he left The Daily Show.
The Problem With Jon Stewart is another prized feather in Apple TV Plus’ quiver, which has struck big so far with Ted Lasso and The Morning Show, and hopes to have success with new shows like Schmigadoon, Invasion and The Foundation, among others.
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Michael Balderston is What to Watch’s assistant managing editor and lead movie writer, covering movies coming to theaters, writing movie reviews and highlighting new and classic movies on streaming services; he also covers a range of TV shows, including those in the Taylor Sheridan universe, Slow Horses, Only Murders in the Building, Jeopardy!, Saturday Night Live and more, as well as the best ways to watch some major US sporting events.
Based outside of Washington, D.C., Michael's previous experience includes writing for Awards Circuit, TV Technology and The Wrap.
Michael’s favorite movie of all time is Casablanca, while his favorite TV show is Seinfeld. Some 2025 favorites include One of Them Days and Black Bag for movies, and The Pitt on TV. Follow on Letterboxd to keep up with what I'm watching.