‘The Problem With Jon Stewart’ Is Good, But Can It Be Effective?

The first episode of AppleTV+’s The Problem With Jon Stewart (which is available to stream on Apple TV+) reminds me of Stewart’s remarkable “it’s not a fucking game” takedown of CNBC’s Jim Cramer for his and his network’s rah-rah behavior during and in the run-up to the 2008 financial and housing market crisis. Watch the clip for greater context, but Stewart was, in effect, a prosecutor, countering Cramer’s spin and efforts to come off as a “doe-eyed innocent” by showing his hypocrisy in real-time. It was a moment that was highly satisfying and which illuminated Cramer’s bullshit for all who chose to see it.

The title of Stewart’s Apple TV+ debut is “War.” Specifically, it’s about the tragedy of soldiers suffering from long-term medical issues due to their exposure to burn pits and the bureaucratic tangle that stands in the way of us taking care of them.

If you’ve followed Stewart all these years, you know this issue runs in parallel to his efforts fighting Congress and bureaucrats for Ground Zero first responders and their long-term care. So the empathy and passion are doubtless, and it really comes through here when he’s talking, in studio, with veterans living through the consequences of this toxic exposure and the ensuing inaction. It also comes through when he is, once again, using his access to act as a pseudo prosecutor while talking with Denis McDonough, the US Secretary for Veterans Affairs.

I don’t want to take away from the impact of seeing Stewart juke past mollifying “I’m on your side, buddy” tactics to pose sound and tough questions to McDonough. Seeing it is kind of the point. But I will say that, while this is a very different situation with different circumstances, it illuminates the bullshit blocking the way on this issue and it’s similarly satisfying to the Cramer takedown, albeit in more of a truth-to-power (no-matter-who-is-in-power) kinda way.

In these conversations and in the way Stewart approaches and experiences them it becomes clear that The Problem With Jon Stewart is going to be very good. Is it going to be effective? And how is that even defined now? Those are more complicated questions. Before we get into them, though, we need to spend some time talking about Stewart’s Daily Show and the six years since he left.

In many ways, Stewart’s 2015 exit proved the power of his legacy. Late-night had an awakening. Daily Show alums Sam Bee, John Oliver, Trevor Noah, Jordan Klepper, Larry Wilmore, Hasan Minhaj, Stephen Colbert, and Roy Wood all made noise in the post-Stewart era through their own shows, docs, and other projects that were largely set in the late-night space. Collectively, that work helped to shape and (more importantly) examine the conversation while diving deeper into often overlooked single issues. They’ve also packaged their message in creative ways engineered to reach audiences that detached from standard TV viewing. The impact is clear and widespread, primed for Stewart to come back and add to what his peers have done. You just have to acknowledge the limitations of the form to not get distracted.

It’s a fallacy to think that a TV show, no matter how well-intentioned and well-oiled, can singlehandedly change the world or swing a sword of truth so powerful that it can pierce the bomb shelter thick walls of our ideological bubbles. Jon Stewart gutting his way through six more years at his old desk would not have stopped the ascent of Donald Trump or lessened the chaos of a presidency that took a wrecking ball to American life. We know this because, at the height of his powers, with next to no competition and a media landscape that was less splintered and more focused, Stewart’s constant pushback against the Bush administration failed to put John Kerry in office in 2004. But that’s not a mark against Stewart and it doesn’t make irrelevant what he can do or what his peers did in his absence simply because they never found the right combination of phrases to awaken half of the country and cancel Trump. That’s not really their job.

If you are over 30, you were raised to believe in the decimating force of the gotcha moment. A sex scandal, a crude gaffe, and revelations of corruption or hypocrisy would end careers or render politicians and pundits irrelevant. The Stewart Daily Show leaned heavily on the wow factor of those last two even as their power clearly eroded. It was still thrilling to see, even if it never brought the warranted results because politicians long ago found pockets of acceptance for their ill deeds, upending the need for broad approval. Because if you’ve got 100% of 40% of the voters, you can mud sling and con your way to the other 10.1%. That’s the key to Trumpism, but its roots are in the way politics and politicians have been covered for years.

As Trevor Noah told me in 2017 when speaking about the evolution of his Daily Show, “hypocrisy and shame don’t hold the power that they once did.” This was six months before Nazis brought violence to Charlottesville, Virginia, prompting President Trump’s disastrous “fine people, on both sides” response. And while there were condemnations from politicians on the right, most re-bent the knee as the mainstream coverage changed from a rising scream to a fading memory. Suddenly, we were all made to accept that that’s just the kind of thing a President says in the era of tear-sipping politics where the points are doubled if you tell the opposing side to fuck their feelings. This is the “game” Jon Stewart is walking back into with his new show.

Apple TV+

It’s interesting how far away from his Daily Show this new series is. Stewart has ditched the suits and celebrities that came with the talk show facade. The set is homey instead of slick. At the moment, it seems that correspondents have been tossed in favor of intimate roundtable micro-chats between Stewart and his diverse staff. Clips play a role, but more as a sort of opening statement. The Daily Show wasn’t inauthentic, but this is somehow more authentic. Something that may be a result of it feeling less concerned with those efforts to be a comedy show while leading with humanity, empathy, and nuance. Which, I suppose, we can attribute to the power of being Jon Stewart and being able to worry exclusively about being good and doing the show you want and not so much about pulling viral moments or adapting to network notes.

I’m going to close as I began, by talking about satisfaction, effectiveness, and the value of identifying bullshit.

It feels fantastic to luxuriate in the moments when Stewart lights up a powerful person to the point where they stammer. It gives off the illusion of a consequence. But Jon Stewart’s value isn’t as a tank, it’s as an armory.

When I said Stewart illuminated the bullshit for all who chose to see, it was a purposeful distinction. We know not everybody chooses to see it, either because it offends their political bias or because they’re tired from apocalyptic headlines and the perfect circle of villainy, ineffectiveness, and fear coming from the halls of power. Cynicism is such a natural response to all of it. Pulling away too. I don’t watch as much late-night, Oliver, Bee, or Noah as I used to because, to an extent, it all starts to blend together and nothing seems to change. Maybe Stewart’s show will lose me too, but for now, I’m seeing this very personal, very deliberate conversation as something unique (even if that may be something of a mirage) and holding out hope.

It’s so easy to look at these shows and think that nothing that’s said will change anything. And again, directly, they will not. But we waste too much time thinking about the supposedly necessary correlation between calling out bullshit and punishing the bullshitters. We really have to forget all of that and realize that there are people who fight and feel empathy for true victims. People who need a light in the dark sometimes because we often ignore them. And so, if this show, and these shows, can deliver information and inspiration to those people in ways that get into the bones and bolster their causes and their resolve to outlast the bullshit, then that’s the definition of effectiveness. And that’s how, slowly, the game that isn’t a game gets won.

‘The Problem With Jon Stewart’ is available to stream on Apple TV+ with new episodes airing bi-weekly and a podcast launching new content weekly.