I was originally just going to make this post about TV shows that are hard to watch now, but decided to include all media. What I mean by hard to watch is it's either super dated due to what has occured in the world, seeing what used to be is painful ("the world you grew up in is lost" meme), or seeing old media one can now see the progression of leftism and what was slightly obnoxious then is now understood to be the beginning of something much worse.
An example of the latter is Burn Notice. I love that show, but the serious daddy issues and pointless drama is a little hard to stomach nowadays, and I can't stand Fiona's proto girl boss crap. She even has the botoxed/ heavy makeup face of modern thots. Or Dukes of Hazard had an episode which featured the blue pill storyline of love. Two lady drivers come into town and show up the Duke boys in every way. Then their evil exes show up and the Duke boys have to save the fair maidens, despite them being better than them in every way. Only once the boys beat the exes do the ladies show their love towards them... An entire episode geared towards white knighting/ simping, with the women both being super independent are more awesome than the men and super damsels in distress in need of protection from bad men they used to date.
3rd reason: oversaturation and what was once a cool twist becoming the norm. Like old whedon stuff.
Try watching firefly or aliens 4 now. Oh sure you might have thought aliens 4 was bad then (you were wrong), but now after the decade of marvel and whedonisms, you will be clawing your ear drums out to end the pain. The quips are aggravating and immersion breaking. But it applies to the good as well, firefly won't hit the same.
I think a lot of the subversion stuff is like that too. Watchmen was maybe fun when every other superhero was earnest. Now it would be subversive to play it straight and not have morally gray slop.
The same could be said for Buffy the vampire slayer.