From saying “Yuck” about the thought of Caitlyn Jenner’s body, to trivializing the trans experience by equating it to the “transracial” Rachel Dolezal, Chappelle doesn’t pull any punches with the trans jokes. This kind of humor can be handled properly, but Chappelle wrecks his credibility outright by saying “I don’t understand [trans people], either.”

He makes it very clear that he knows nothing about his subject matter, tainting whatever humor you manage to find in these jokes with a lack of understanding. The jokes feel more like an attack more than any kind of lighthearted observation.

That’s the difference between Chappelle and someone like comedian Ian Harvie — Chappelle’s jokes don’t come from an appreciation; they come from confusion and fear.

What’s worse is his audience gives him all the support in the world, egging on his ignorance; as he rips through all of his trans material, the audience becomes progressively empowered to react honestly.

First, the laughs seem like the ones your parents give when you’re in the room and someone tells a not-so-PC joke. They’re half ashamed to laugh because they realize how grossly offensive it is, but aren’t going to deny that it appeals to a less sensible side of them.

When Chappelle suggests he slept with a trans woman in a later bit, the emboldened crowd expresses audible disgust. He responds with “Oh, grow up. That doesn’t make me gay” when they groan at this.

It’s difficult to just sit and laugh when trans people (and now gay people) are subjected to a twisted kind of amused revulsion by all the cis and straight people present. This is not humor so much as it is a showcase of all these people’s hidden prejudices, revealing privilege and an unsettling openness to bigoted rhetoric.

https://studybreaks.com/culture/dave-chappelle-transphobic/