I've been rewatching himym lately, and it's a pretty interesting experience. I expected to cringe away after a few episodes, both due to dated jokes and my tastes having changed since I watched it, but for the most part it's actually held up quite good, at least on the humor side. And then out of nowhere the show will be ripping on girls with daddy issues or blondes or stereotyping gay people, and then just as suddenly move on.

And that's the main thing that's keeping me watching. It's this weird blend of holding up extremely well and then simultaneously doing a complete 180. It doesn't happen often enough that I think it goes too far or ends up being mean, though any one of those scenes would be comfortably outrageous enough to get the entire thing cancelled if it happened today, so for now there's this juxtaposition of casually different popular culture mixed in with all the other references that creates an experience at least as entertaining as the show itself.

This song is a perfect example of what I mean.

 

I love rewatching this show, I've lost count of how many times I've watched this and community. It really does hold up in a lot of ways as you said, and it's still consistently funny start to end. Aside from the things you've mentioned, one thing that has become clear to me over the years is how most of the cast are awful people, not just Barney. Especially Lily who I cannot stand at points.

 

Banger show. Very funny if you don’t take issues like those mentioned above super seriously.

Whenever I rewatch this, I tend to focus on the humor and witty interactions rather than the serious life/drama issues in the overarching plot. This improves me rewatching experience significantly.

 

Friends is similar, although being older the awkward bits are more common.

I do wonder if we get to the point they get cancelled or edited for being to away from the norm now.

 

I’ve been watching that show. I’m on season eight.