It was probably inevitable that Dave Chappelle would do the most provocative comedy on Bill Cosby.

After all, no comic has done more button-pushing jokes about the crime and punishment of famous black men. Mr. Chappelle waded into the sex scandals of Michael Jackson and R. Kelly (the “How old is 15 really?” bit), and last year I saw him quiet an uncomfortable crowd as he mused on a rape case in the news. Yet in his terrific new special, “The Age of Spin” — being released Tuesday on Netflix along with an uneven but still riveting second hour, “Deep in the Heart of Texas” — the tension rose when Mr. Chappelle brought up fan reaction to his jokes about the Cosby rape accusations.

Is Mr. Chappelle about to be the first major comic to defend Mr. Cosby? He is not, but what he does do is articulate more passionately than anyone else in popular culture what a devastating loss it is that the cultural legacy of Mr. Cosby is being wiped away from popular memory. As a comic who grew up in the 1970s and ’80s, Mr. Chappelle explains how much Mr. Cosby meant to him without playing down the accusations. Still, it takes guts to close a show, as he does, with an argument for complexity in our assessment of Mr. Cosby, and Mr. Chappelle’s daring, his insistence on challenging his audience, his eagerness to go there, is what makes the arrival of these specials such an invigorating — and possibly polarizing — event.

When Mr. Chappelle abruptly left his show on Comedy Central in 2005, it didn’t just take him off television. It radically changed his image and career. In the previous seven years, he produced three stand-up specials for television. He hasn’t done any more until now, but he has toured constantly, becoming a performer you need to see live. I’ve gone to more than a half-dozen of these shows and find that they generally fall into two categories: a tight, polished hour of jokes with a strong thematic core, or a rambling mosey through material interrupted by combative chats with the audience. “The Age of Spin” is the first kind; “Deep in the Heart” is more the other.

They both lean heavily on giddily funny stories, self-referential bits about previous shows going badly wrong and some explosively silly sex jokes. There’s no mention of President Trump, but an imagined movie pitch about a superhero who fights Mexicans might be an allusion. Mr. Chappelle also compares himself to peers, flashing jealousy over the success of Kevin Hart and throwing a jab at Key & Peele for “doing my show” as well as performing a pretty fantastic impression of Katt Williams.