Maybe It’s Time for Jon Stewart to Step Back

On Monday night’s show, the two generational ends of the spectrum were on display as Stewart interviewed New York City mayoral candidate Zohran Mamdani. With days until that election, Mamdani is navigating the consequences of the existential fear that younger, more energetic, less experienced politicians inspire in those who have become fat and rich off the scam of our cracked-out system. Anti-Islamic messaging and fear-baiting, MAGA talking points, and warnings of chaos and anarchy have been trotted out in opposition to him. This is coming from both sides of the aisle – largely from Mamdani’s once-vanquished but still flopping rival, Andrew Cuomo, as he gropes for a line of attack that’ll save him. 

On The Daily Show, Mamdani found a safe space, giving him a chance to benefit from the optics of Stewart, the media’s liberal lion, nodding in approval and beaming with pride. But while they surely align on plenty, I couldn’t help but observe a distance between the 34-year-old relative political outsider and the 62-year-old comic/pundit. Particularly when Stewart, a millionaire from the Jersey suburbs, mentioned his experiences living in New York in the ‘80s and offered well-meaning but obvious advice on running the city. 

There’s a relevant line from Mamdani during the interview that really connects to my thoughts about Stewart in this moment. When talking about governing with a coalition of people, Mamdani said, “I think youth gives you an innate sense of possibility and a humility that you don’t know everything.”

Now, while I don’t remember possessing any measure of “humility” leading to the idea that I didn’t “know everything” when I was in my 20s and early 30s, Mamdani paints a stirring picture in his advocacy for the oft-misunderstood and under utilized young voter. A bloc that is constantly talked at and sized up, but rarely offered a representative from their peer group, like Mamdani. And as it is in politics, so too is it in media where the dominant profile is white, male, middle aged, and insulated from a lot of cruel reality by money and station. 

While Stewart is still an enjoyable, reliable watch in moments of chaos that need context and a reality check, his tone is unendingly authoritative as he processes political absurdity through his own experiences and concept of right and wrong. And while it often hits, it can also be limited by those experiences as an old, successful, white guy. His dispatches, which I have praised many times, can feel more like a sermon – calls to nod, not calls to self-investigate and invest. We are witnesses to his outrage, not co-conspirators in a conversation. It’s all very in-line with a time when there were fewer platforms and bullhorns. But this is not that time. Jon Stewart is God to a certain niche, but the hierarchy of niches may need reorganization.  

Stewart’s return to The Daily Show has squared nicely with the show becoming a greater platform for its talented roster of correspondents with Ronny Chieng, Jordan Klepper, Desi Lydic, Michael Kosta, and (more recently) Josh Johnson getting the chance to host when Stewart isn’t. Were he to leave completely, I definitely worry that the show would soon follow because Stewart has been as much a shield as a target. But those are the same concerns that came up when he left the first time, making way for Trevor Noah’s revitalization of the show. That happened in a very different late night landscape, but it still might be worth the risk to see if another next gen host can connect with a next gen audience again, tapping into what should be a youth movement in politics if parties read the room and acknowledge the wrinkled, decrepit faces of their often regressive, bitter, fear-based, and cynical organizations. 

I don’t know how this fan-casting would look. A new regular host? A semi-regular host with Stewart occasionally popping by to put forth his righteous elder energy like a new version of the show’s Back In Black segments with screamo comic Lewis Black? 

Of the correspondents, Johnson feels like the best fit to get the big job. Joining as a correspondent in 2024 after writing on the show for years, Johnson has impressed in his initial hosting stints. But his true, enticing potential is revealed in his absolutely prolific stand-up work and mastery of YouTube. While most comics ration material, squirreling jokes away for biennial comedy specials on Netflix or HBO, Johnson drops fresh 45 minute sets every couple of weeks, leading his live audience on a ride that eventually speaks on the biggest issues of the day with a lot of funny and charming asides. 

Johnson is not a typical set-up/punchline/repeat comic, he’s a gifted storyteller who draws you in with casual observations that connect to how intelligence and financial success in the tech sector don’t go hand in hand in one video. In another, he goes from recalled Wal-Mart shrimp to a joke about a chosen crustacean causing RFK Jr. gastrointestinal distress.

All the while, the punctuation at the end of what Johnson is building toward often feels more like an eye roll over the weirdness of the ruling right and whatever has gone viral, not a fist repeatedly pounding on a table. While that style might not be a fit for every situation, it taps into the kind of “Emperor has no clothes” point-and-laughs that were working during the election. You know, before the political consultant class shut down the “isn’t that weird?” phase, ignoring its impact as ego kryptonite that clearly got under the skin of Trump and the MAGA squad of big, tough, cool guys who everyone loves and no one is supposed to laugh at.

With a more inviting style and the evident curiosity of a younger mind, Johnson could not be more right for right now, capable of reaching a new audience because he’s more in-tune with their experiences and isn’t at a distance and on a pedestal. He relates and is more relatable, less irritable.

While Stewart has about a quarter century proving he’s the GOAT when it comes to finding comedy amidst seething indignation, hypocrisy signaling, and righteous lectures, and while we’re able to vicariously vent some steam from that, it also recirculates the bleakness. If hope is going to seep into our broken machine, it’s going to happen because of new messengers, messages, methods, and established leaders recognizing the arrival of a future where they aren’t the main characters. Maybe Jon Stewart can show Chuck Schumer how.