Television

I'm gonna say the Dick VanDyke show has aged extremely well overall.

Then again, you have stuff that's a little more recent, so there's less "era shock" involved. Stuff like NYPD Blues, ER, and the CSI type shows. There's some cultural references in those shows that misses, but they don't feel as alien to people that were raised with internet access.

But I would still say that the DvD show manages to still hit with its comedy, despite the cultural shift. And comedy is harder to insulate against cultural shifts. There's only a handful of the old sitcoms that work for young adults now, and that's one of them. Kids don't get it as much, but I think that's more about them being kids than the culture. A lot of kids still enjoy older shows, just not DvD, hence my opinion on that.

Now, worst? The Honeymooners. There's just too much reliance on humor that really only works for an older generation, and the near constant threat of violence (no matter how unthreatening it actually is) puts a lot of people off. If you look at I love Lucy, which has a slightly less ugly threat of spanking here and there, along with the regular built in patriarchy-as-humor battle of the sexes thing; it still works outside of it because Lucy does the nigh slapstick bits that allow you to just ignore the rest.

You could point to the older westerns as examples of not aging well, but that's the whole genre of tv western having issues that make it harder to watch now, not shows in specific. There's still some that work well enough, but not enough to be able to only have one or two bad examples left.

The advent of stuff like tubi that run older shows means that some kids are being exposed to older tv, and if you talk to teenagers in specific, you can get an idea of what kind of shows have lost relevance because of culture shift. Not that there's a monolithic, sweeping consensus, but you can pick up what is and isn't working well enough for kids to watch on their own time rather than when they don't have a choice. Obviously, sample size matters, but for casual conversation, the above is what I've noticed.