The Problem With Jon Stewart’s new talk show might be his own tremendous shadow

If you were to ask any major talk show host during the mid-1990s who their single biggest influence was, they would likely say one name: Johnny Carson. A decade later, it was probably David Letterman. However, today that name is very likely Jon Stewart, whose 16-year run on Comedy Central’s The Daily Show took the superficial format of Saturday Night Live’s “Weekend Update” and elevated it beyond simple fake news and pop culture references.

Four nights a week, Stewart delivered incisive satirical commentary about the very real political issues impacting the world. Four former Daily Show correspondents now host their own talk shows that each bear Stewart’s mark in some way: Stephen Colbert (The Late Show), John Oliver (Last Week Tonight), Samantha Bee (Full Frontal), and his eventual Daily Show successor Trevor Noah. Former Daily Show correspondent Wyatt Cenac hosted Problem Areas in 2018 (Stewart has acknowledged the similarity in titles).

That’s a tremendous legacy on its own, but it doesn’t end there: Seth Meyers (Late Night) might’ve hosted Weekend Update for years, but his regular “Closer Look” segments are more like The Daily Show than Letterman’s old Viewer Mail bits.

Stewart left The Daily Show in 2015 at the top of his game. Now, he’s returned with a new Apple TV+ series, which premieres September 30. The open credits cycle through several potential titles (The Money Grab With Jon Stewart, The Monthly Show With Jon Stewart, The Trouble With Jon Stewart) before settling on The Problem With Jon Stewart, but the cold open makes it clear there’s no actual confusion about the show Stewart wants to create.

Seated at a table during a producers meeting, Stewart explicitly lays out the format—monologue that introduces this week’s “problem,” then an interview segment devoted to those the problem directly impacts, followed by an interview with someone important who could possibly help.

The intro also reveals the faces of the people working with Stewart, and it’s a sharp contrast to his notoriously white male staff on The Daily Show, which he said he regretted in an interview last year on The Breakfast Club. Stewart has made good on what he described as an obligation to “actively dismantle” a discriminatory system. The show’s head writer, Chelsea Devantez, is a woman, and the executive producer, Brinda Adhikari, is a woman of color. And she’s not alone! This is a refreshing change.

In his last episode on The Daily Show, Stewart declared the world “demonstrably worse than when I started this!” This wasn’t entirely hyperbole or (in my case) Gen-X nostalgia speaking. Stewart took over from original host Craig Kilborn in 1999. Bill Clinton was still in office, and the Supreme Court hadn’t yet installed George W. Bush in the White House. Then came 9/11 and the Iraq War. Donald Trump wasn’t yet president when Stewart quit, but he was no longer the obvious punchline Stewart had assumed when he’d walked down that escalator in June 2015.

Stewart told Charlie Rose in 1997 that the key to his comedy was recognizing life’s absurdities. But the Trump era, arguably still ongoing, wasn’t simply absurd. It was devastatingly real. Stewart admirably doesn’t try to return to a simpler milieu. He seems focused on making the change he wants to see in the world.

That said, the first “problem” Stewart tackles is familiar terrain—the country’s shoddy treatment of its military veterans. Stewart has advocated on behalf of 9/11 first responders, who suffered from the long-term effects of a terrorist attack, but these Iraq War veterans are victims of not-so-friendly fire. They were exposed to toxic fumes from what’s known as “burn pits,” where U.S. military contractors dumped trash and set it aflame with jet fuel. “Trash” is too benign a word. The pits contained piles of human feces and random body parts. There are veterans still dying from cancer, but the government would prefer to bury them as well, claiming that there’s no proven link between otherwise healthy young men who now struggle to breathe or have been driven to attempted suicide from their chronic pain.

This isn’t funny material, obviously, but Stewart is too personally invested to make the first segment’s few jokes land. Here, the show does not quite meet the standard set by John Oliver’s deep dives on a topic that are informative yet never less than hilarious. Amber Ruffin is also able to deliver “Schoolhouse Rock”-style studies on racism that still manage to leave you laughing. Stewart struggles with this balance to the extent he actually tries (the few overt efforts fall flat).

The Problem With Jon Stewart is ultimately more advocacy than activism, and while that’s consistent with Stewart’s past work, it lacks bite. Our current political climate is so absurd that even actual news anchors, such as MSNBC’s Brian Williams and CNN’s Anderson Cooper and Jake Tapper, frequently have satirical segments where they perform more like Stewart than the stiff, buttoned-up Walter Cronkite wannabes parodied on “Weekend Update” and the original Daily Show with Craig Kilborn. They exist in a post-Stewart reality. The challenge for Stewart is whether he can truly thrive in the world he’s created.

Stray observations

• The interview segments were never my favorite part of Stewart’s Daily Show. This episode’s interview with Denis R. McDonough is awkward, and unfortunately, McDonough, who seems well-meaning, comes off like Martin Short’s shady businessman in a 60 Minutes spoof on Saturday Night Live. That was funny, of course. This isn’t.
• It seems even more impressive now that John Oliver can keep my attention on a single subject for 30 minutes.
• I know it seems like an odd criticism given The Daily Show format, but Stewart could really use someone to banter with on the show.