Any time these older comedians get all anti woke it IS cringe. because it does come off as old man yelling at clouds.
I feel like a millenail or gen Z comedian could poke fun at woke culture and actually have success because, at the very least, since they are a part of the "woke generation" they might actually have fresh takes on things. I don't know if Chappelle or Burr have done it, but every time I hear a comedian go "well my pronouns are john deere tractor and i identify as farming equipment ahahahah" or something I want to scream because it's not a funny take, and it's been done to death.