This is a great piece, and highly worth reading if you've ever heard of Megatokyo or ever read similar webcomics from the 2000s.
There's something that this piece touches upon which is that, sometimes when a cultural artifact from a certain era gets streeeeeeeeetched into the present era [because it still hasn't ended], it can create these really unsettling feelings.
Like, there's something about Megatokyo, Penny Arcade, etc etc that feel like they are truly FROM that time period, but displaced into the current era. It's like when I visit my parents and hear them say the word "UberEats" or "TikTok", it's like reality is phasing through time.
There are creators who do stuff for a while but who naturally change over time in a way that sort of "fits" the current era, clearly influenced by things and cultural objects that have happened recently. I feel like when this happens, it's usually an indication that the creator is either more in-touch with what's going on in pop culture or they're much more empathetic and willing to learn new perspectives in general. Or, if I want to be more generous, a sign that the creator has more free TIME and OPPORTUNITY to learn new perspectives and new pop culture.
Then there are creators, and creations....where that doesn't feel like it's the case. Sometimes that can be delightful, like a nostalgic throwback (which i often love), but other times it has almost a horror movie vibe to it. Like the mistakes of the past are still hiding in closed boxes and between the pages of books, waiting to crawl out.