I'd done some digging and didn't run across much of that.
That's because you must have done only light digging after the transgender controversy, which dwarfed everything else he did. I had followed him somewhat and then even more after the Hartford thing because I still lived there when it happened. (I did not attend because I figured it would be an uncomfortable and bitter race humor night because I'd heard him talk about his show and his new attitude about it, including converting to Islam as his new religion, and my suspicions were duly confirmed.)
You can chalk people's distaste up to the big transgender issue, but I don't think that's what we're all reacting to, at least those of us that knew of him and about him before the whole thing became a ridiculous conflagration with two emotional sides arguing about a flashpoint issue and making each other look even worse than they had looked before when a neutral observer might have been unable to imagine it any worse than it already was.
Here's the Hartford thing. For a race-centric take, read NPR and remember what NPR is:
https://www.npr.org/2013/09/06/219762592/after-dave-chappelle-hates-on-hartford-whos-to-blame
For a quote about why he hated his own show, see Slate Magazine:
"One of the reasons Chappelle abandoned his sketch comedy series at its peak of popularity was that he grew uncomfortable with the response to his racially charged humor from white audiences. During the taping of an ill-fated sketch in which he donned blackface as a “
black-pixie” who prodded black people to perform as stereotypes, Chappelle noticed that one white male audience member seemed to find it a little
too funny. '
When he laughed, it made me uncomfortable,” he said. “As a matter of fact, that was the last thing I shot before I told myself I gotta take ****ing time out after this. Because my head almost exploded.' Lewis’ reading of Thursday night’s performance seems plausible given this history."'
Yeah, Dave, that white guy laughing thing seems real rational and with it.
So Jayrod, this was hardly a "digging" effort. I remember it from way back when and was able to find it easily, down to the quote in Slate I was thinking of. It was like front-and-center. I think you're too worried about that flashpoint cause and not about why people might also dislike him. It's like missing the forest for the trees.