Spiteful comedy feels good as long as it punches up. Not necessarily funny, but schadenfreude, cathartic, or just relief seeing them ‘get taken down a peg.’ It invites controversy when the artist and the audience disagree on the power structure. Chappellle falls apart around transgender, because he thinks he’s punching up to that group, where I imagine most people believe that trans are close to the bottom of the oppression spectrum. Chappelle’s argument basically being something like, “Well, they can ‘pass’ if they just match gender presentation to biological sex, and a lot of them are white.,” but having to hide your membership in a group is the opposite of power.