keep in mind that humour usually involves making fun of people and it doesn’t make people anti-whatever-they’re-making-fun-of:
Generally sure, but Chappelle literally says “I’m team TERF”. There’s no joke there, he’s just announcing he’s transphobic.
There’s a good Terry Pratchett quote the situation made me think of: “Satire is meant to ridicule power. If you are laughing at people who are hurting, it’s not satire, it’s bullying.” And we should all know how much the trans community are hurting. Dave Chappelle has a lot of power and influence as a prominent comedian and he should use that platform for good instead of attacking a marginalised group.