This is probably a pretty good place to point out that reports of bullying against LGBTQ people in US schools have been rising rapidly for the past few years, tracking closely with the rise of anti-LGBTQ violence in society at large. Transgender people are disproportionately the targets of this bullying and violence.
It’s worth noting that the kinds of jokes that Chappelle used in his special are the same jokes that real bullies use in real life to hurt real trans people.
I don’t know about you, but when I watched the special I didn’t get the sense that Chappelle was making fun of the bullies when he retold their jokes.
But I can almost put that aside when thinking about my major objection to the special, which is the Chappelle just doesn’t know what he’s talking about. I’m not used to that from him. I’m used to incisive social commentary, well informed social commentary expressed through comedy.
Chappelle did not do his homework. He does not understand trans people or trans issues or trans challenges. The jokes he made fall flat or sound transphobic because he doesn’t know what he’s talking about, and that’s a problem.