This was painful to write because I was a huge Jon Stewart fan in college:
Then there was the sneering superficiality of Stewart’s treatment of a medical scandal I’ve studied closely, which he framed as the brave “new dawn of gender and sex complexity, where those who don’t fit into a simple binary are meant to be seen with humanity”. Stewart studiously avoided asking any of the obvious questions about the sudden profusion of (often objectively laughable) gender identities — despite his usual commitment to asking the obvious questions — and then mocked a caricature of that which he had not bothered to understand. The more I watched, the more the laughter in the studio sounded canned. Or maybe it was just hard to imagine anyone responding so enthusiastically to what Stewart had to offer.
As someone who grew up watching The Daily Show, Stewart’s trajectory over the past few years has been painful to observe — and not just in the way that any bombed comedy set pains the audience. Stewart’s return to comedy raises some uncomfortable personal questions. Did I change? Did he change? In other words: what was I laughing at all those years? Was Stewart always so righteous and insufferable? Had I failed to see it because I’d been righteous and insufferable in just the same way? Were his interviews always so predictable? Somehow, the man whose show I couldn’t miss became the man whose every monologue I could have scripted had I been bored enough to try.
But whether Stewart changed or I did, the times certainly have. It turns out strict orthodoxy is bad for comedians and other living things.
Like you, I was also a big fan of Stewart in his Daily Show days, except that I was already in my 50s. Also, like you, since then I have found him just as you have. I can't stomach him anymore.
I am 60 and have found time and again this in my own life. Additionally it is very hard, in my opinion, to listen to a generalist when one possesses a deep understanding of a particular subject.
I have a pile of books that stand as reminders of some of the nonsense I was convinced by 35 years ago. They help me remain patient with my kids and the young people I work with.
To me I think of this case of John Stewart just having a particular tool that is ill suited to this sort of issue. Thinking of health care for 9/11 responders he has a pretty good tool to get more attention. But when it comes to something like sex/gender you need the Bill Burr types who are prepared to challenge not what they know but rather how they think