The problem is the jokes aren't funny. Or even really jokes. It's just the same hateful garbage that you'll find in any right wing comment section with no clever twist or respect for the humanity of the people being made fun of. It's all variations on "haw haw, these people are pretending to be something they're not, ew gross". It's not true, it's not "keeping it real", it's not insightful, and anyone who actually knows or cares about the trans community knows that hearing that all the time will drive some people to kill themselves. Maybe even worse than that, it'll foster that attitude in people even less compassionate that Dave Chappelle, who I don't think has any particular malice toward individual trans people, but he's telling those who do that they're right.

There's definitely humor to be had about the trans community, just visit any trans meme board and you'll find it. There are stereotypes and self-deprecation and tons of really dark humor going on. What's coming out of Chappelle's mouth isn't that, it's just undercooked right wing bigotry.