I mean, Richard Pryor’s comedy is sort of known for honesty. But it’s not all or none. Prior has a classic joke about he has to stop drinking because he keeps waking up and he’s driving 90 mph. Do we think he really woke up at the wheel going 90 mph? Do we think he did so repeatedly, as the joke implies? Would the joke still be funny if he had to say “in this joke, I’m pretending to be a habitual alcoholic and speeder”? No, probably not.

Carlin used to make classic funny faces when he delivered those sort of punchlines, where the thing he’s pretending to be, while still being relatable, is absurd.

You need to listen to him for a while and hear a lot of different sets. You can listen to him speak at length about compassion and love for everyone. You can look at his organizing and political work. When he delivers that first joke in the newest special, about when he met Jim Carrey whilst he was in the process of portraying Andy Kaufman, and he goes through this long story about how his father had died and he was depressed, and meeting Jim Carrey was the first thing in a long time that made him smile. He doesn’t really think meeting a trans person is the same as having to pretend he was talking to Andy Kaufman when he could clearly see that he was talking to Jim Carrey. One hint that he is joking is the silly face he makes upon delivering the punchline, and the fact that he laughs after he says it. And again, you could just know him from his extensive body of work on and off stage and you’d realize that he wouldn’t incite anyone against any minority; he is a minority, in America, and has pretty advanced empathy for the minority experience, including the trans experience.

Maybe you have to know him to find the joke funny? I guess if you wrongly presume he is being serious, he would sound like a bigot, which is apparently how you and many others are hearing him. I wonder if when you listen to Chappelle, there’s some unconscious bias where you perceive black men as more aggressive or threatening, or more serious, than they are. Perhaps you have biases that can obscure your perceptions of body language or facial expressions of black men. Very common. Test yourself: https://implicit.harvard.edu/implicit/user/agg/blindspot/indexrk.htm

I think Chappelle, in that opening joke, is pretending that he doesn’t appreciate the difference between, on the one hand, a white male actor pretending to be another white male actor in exchange for millions of dollars, and on the other, a person in gender transition. If he wasn’t pretending, the joke wouldn’t be funny. It would be sad and hateful. It’s the whole situation though, that makes it funny. He’s talking so seriously about how his father died and then makes a trans joke. It reminds of The Aristocrats joke, which as a fan of comedy I find hilarious. Another hint that he’s pretending is the context: he’s a comedian telling a joke; he doesn’t have to say “I’m only joking, I don’t really believe that.”

I don’t know if it was you or someone else that said “it’s okay to joke about trans people but not to punch down.” I agree. I don’t see it that opening joke as punching down, I see it as empathy for trans people. Comedy is empathy. You cannot joke or laugh about something unless you can relate to it and put yourself in the joke. This is why conservative “comedy” is virtually never funny, they lack empathy.

It’s impossible to convince someone a joke is funny if they don’t laugh, so I won’t bother with trying to convince you. And that’s okay. But I can assure you I am not a bigot or a shitty person, or a conservative, or uneducated. Rather, I’m a vehement anti racist, an attorney for regular people and fun lefty causes, and I found that opening joke hilarious. I wouldn’t ever tell it, but I’m not a world renowned stand up comic, up on stage, trying and succeeding at making thousands of paying strangers laugh at what I say.