He's got a really niche audience. People who think they're all cool just for being "politically incorrect." Like other comedians in the american scene.
I used to like his comedy – great storyteller and all. But lately, it's like his specials follow this routine: some jokes on how racism's still an issue, mixed with a bit of him claiming he's the top comedian alive. And let's not forget the bits where he suggests making fun of people's choices is all in good fun.
The crowd at these specials? Feels like a bunch of yes men, laughing and clapping at every word from Chappelle. It makes watching his stuff on Netflix a bit of a struggle for me.
Don't get me wrong, the guy's talented. Awesome timing and storytelling. But nowadays, being a badass doesn't mean being a bully, and it seems like that shift bugs him and his entourage of yes men. That's probably why his specials come off a bit too harsh, at least in my book.