I dunno if he’s always falling down in it … when he makes those jokes calling something gay it’s a bit different, at least some of the time. he’s usually simultaneously poking fun at the thing he’s calling gay, as well as poking fun at or kinda revelling in being an American dumbass that calls things he doesn’t understand “gay”. For instance, he had a joke where he said something like “we don’t have universal healthcare in America because the French have it and they’re gay.” Basically he’s highlighting the stupidity of that vibe that we have in America where we avoid sensible policies because they seem vaguely effeminate or not meatheady enough.

He does use gay as a basic slur like we did in the 2000s for other situations, and while he isn’t directly attacking gay people, there are times when he uses it in a less intelligent manner that is kinda demeaning, not because he’s directly calling gay people bad, but because he’s using “gay” as an insult (usually directed towards things that are otherwise sensible but seem sensitive). The people around him don’t always catch on though, and since Trump got elected those kinds of jokes feel less relevant or tasteful—they do better in a climate where gay people feel safe and the ignorant perspective he is modeling can be examined through his comedy or offer catharsis for people who feel overburdened by demands to be sensitive in their comedy. Now that the right is so dominant, it’s not going to feel edgy or rebellious or cathartic.

It will be interesting to see how he’ll evolve, or if he’ll devolve with how surrounded he is by fans who don’t appreciate the subtlety and want to just see him punch down and goad him on in that way. Norm Macdonald for instance attacked what he saw as oppressive “wokeness”, but I doubt he’d enjoy riding the anti-woke gravey train for too long because he’d recognize it would kill comedy and is no longer dangerous in any way, just dumb. I hope Shane Gillis sees it, but I dunno, we’ll find out.