The Problem With The Problem With Jon Stewart

The first warning sign was that despite being a big fan of The Daily Show back in the day, I never bothered to watch The Problem With Jon Stewart. Now that Apple is cancelling the show due to disagreements over certain topics Stewart wanted to cover, however, I couldn’t help but feel a bit of nostalgia, so I decided to give it a chance before it was gone for good. In the end, though, my intuition was right : the show is fine, but rather uninspired. In the end, The Problem With Jon Stewart has two major issues : the overwhelming sense of corporate control over it all and the desire to cling to the good old days.

Given that the show's cancellation is reportedly a result of Stewart wanting to cover touchy topics like China and artificial intelligence, it’s not shocking that there’s a pervading sense of Apple’s watchful eye throughout the show. After all, since they’re bankrolling it, they expect a certain return on investment - anything that might threaten their commercial interests is strictly off-limits. There is some nuance to this, of course, as Stewart points out some ways in which Apple, too, is somewhat problematic : Apple took a corporate incentive deal to build a new site in North Carolina, a deal which typically encourages states to weaken workers’ rights and take taxpayer money out of education and healthcare.

Some might think this is proof that Apple wasn’t really controlling the show that much. There might be some limitations, but at least they’re willing to be criticised, right? Not exactly. The reality is, even this self-criticism is done for the sake of Apple’s revenue. There’s a sense that since Apple acknowledges doing wrong, they deserve forgiveness because they’re “woke” and understand that they’re part of the problem but can’t help the way society is, just like how a normal person might play into racism and sexism because that’s just how society is. Really, though, putting a company worth literal trillions of dollars on the same level as the average person just trying to get by rings way too hollow. It’s a common trick used in this kind of talk shows, with many hosts poking fun at their parent companies to create an image of free speech and make the company seem more humble. Normally I’m not bothered by it, but it’s just so inescapable in The Problem With Jon Stewart, with multiple name-drops per episode and even product placements for Apple. The result isn’t cute and self-aware, it’s just irritating.

Speaking of self-awareness, that brings us to the other main issue : The Problem With Jon Stewart isn’t made for modern audiences. There’s something about it that just seems so… millennial, which is fine, but it definitely feels like it should have existed in the mid-2010s and not mid-2020s. I struggled to figure out exactly what felt so off about the humour, but I think the best way to explain it is that it’s too quirky and self-deprecating, like it’s trying to be cute only to fail disastrously. One moment that really sticks out is when Stewart suddenly sings a parody of a Hamilton song which ends with him pretending to be… a sexy Jellicle cat? I cannot for the life of me remember the context, but the humour just feels so dated. Stewart left The Daily Show in 2015, and The Problem With Jon Stewart feels like a perfect continuation of it, not because it captures the essence of the original show but rather because it takes you back to that time and makes you cringe.

I’m not saying the show is entirely bad, but I don’t think its cancellation is a huge loss either. It’s a pity, really, because more and more people are getting their news from non-traditional sources, and there was a time when Stewart was a pioneer of that, bringing quality, critical pieces to wide audiences alongside Stephen Colbert. Now, though, Stewart has a host of competitors in the form of TikTok activists and YouTube video-essayists who have a better understanding of the comedy and tone preferences of today. Stewart’s major advantage over them is his access to experts, be they politicians, executives of major companies, or even grassroots activists. He has the budget and connections that can bring those voices together, and perhaps if he’d focused on that, the show would have been more successful. Unfortunately, though, he instead sought to fill a space that had already replaced him.

I still like and admire Jon Stewart, so I hope he finds a way to continue his work, just differently this time. If he focused on smaller issues rather than tackling “racism” or “the economy” in less than an hour, each episode would be more fulfilling - but perhaps he felt he couldn’t, because John Oliver is already doing that. In any case, Stewart is an intelligent and entertaining person who just needs to find his niche again, somewhere far away from intense corporate control like Apple. When he does, we can only hope he finds some younger voices to help bring him to the modern day. For now, though, all I can say is that the cancellation of The Problem With Jon Stewart is no great loss as the problem with Jon Stewart was the show itself.