Look, I'm willing to judge a joke on its on merits but there's some territory that's trickier than others: when the subject is a member of the underclass.
Trans people are literally being legislated today and actively demonized by the right. Do you remember the trans bathroom laws that were all the rage? Do you remember all the attacks by trans people that precipitated them? No, because it's manufactured fear.
You finding pages of individuals speaking out against that and that's terrifying? More manufactured fear.
I'm not sure what iteration of Chappelle's jokes they are addressing in the indiewire piece, but here's what I could find, and it seems very different in tone https://youtu.be/r_EXb8_8xlM
First joke aside (which I'd guess is older material than the rest) if you stick with him and don't cherrypick quotes, it's almost entirely self-deprecating. Even in the Caitlyn Jenner joke, the punchline rests on him acknowledging his own failure to resist his impulses. Don't forget the layer where he is acting out the role of a horrible, insensitive person throughout this so the audience can laugh at his oversimplification and ignorance. That's a big part of comedy and it does not translate over to quotations in prose.
Hopefully I didn't kill the frog, but he's absolutely not punching down from what I could find.
Trans people are literally being legislated today and actively demonized by the right. Do you remember the trans bathroom laws that were all the rage? Do you remember all the attacks by trans people that precipitated them? No, because it's manufactured fear.
You finding pages of individuals speaking out against that and that's terrifying? More manufactured fear.
As to the subject I replied to, Chappelle's jokes, it's addressed here: https://www.indiewire.com/2018/01/dave-chappelle-transgender...
Hooo haw, laugh riot over being tricked to have sex with a tranny! And that Bruce/Caitlyn Jenner, that really grosses me out!? Hee hee hee.
Sorry, but that shit's puerile at best.