My take… I’ve watched several Chappelle specials and loved all of ’em. This is not a defense of Chappelle, just an observation which may or may not be in tune with reality.
I have nothing against anyone in the trans community. I do, however, feel a bit queasy whenever I see Caitlyn Jenner. Same goes for my hero, Bradley (Chelsea) Manning. Trans people are my uncanny valley.
When I worked in NM Pre-K one of my parents was a trans person. The boy’s mother was now his father. The child (his name is Miles and I nicknamed him Smiles) was universally loved by everyone in PreK. The dad was loving and supportive. Still, everytime I interacted with him, I found myself in the uncanny valley.
My point is, perhaps the reason Chappelle makes trans jokes is because he figures some in his audience experience the same uncanny valley as I do. As, maybe, he does. Making jokes is one way to ease the burden of fear. I mean, why do you think there’s black humor? Death jokes?
I did standup on a cruise ship once. The emcee was a bit wary when I explained what I planned, but he went with it, much to the delight of the audience. I was so much younger then…
