Full disclosure: I did not watch all of The Chappelle Show, neither on Comedy Central nor on DVD (which apparently over two million people own, making it one of the top five best-selling DVD TV series of all time). But I still quote it ("I'm strong, Joe Rogan!"), and recognize the references. Even his production company, Pilot Boy Productions, utilizes his ubiquitous catch-phrase, "I'm rich, bitch!" and is the last sound you hear at the end of the two stand-up specials now on Netflix. It's the most fitting part of The Chappelle Show legacy, really.
So far, I've only watched the first one, The Age of Spin: Dave Chappelle Live at the Hollywood Palladium. He starts with a kinetic visual montage of gif-like animations on the topics about to be covered in the comedy hour, followed by a black and white preponderance of self narrated by (whom else?) Morgan Freeman. These are interesting and aesthetically cool, but not funny.
The show starts with a story about getting pulled over with a friend, but in this scenario the driver is not Wayne Brady, it's just a black guy who may not pass a breathalyzer. Chappelle's punchline is that he gets to drive away because weed doesn't register on that sobriety tester, but the his nonchalance about his friend's arrest - as well as his awareness that he probably wouldn't get arrested, seeing as he's Dave Chappelle - makes him come off as a dick, and not a particularly funny one. Good thing you're rich now, ha ha. In the same vein, I didn't think it was funny that he ditched a Flint, MI, benefit (co-hosted by Ava Duvernay and Ryan Coogler!) to go to the Oscars with Chris Rock. I don't really blame him, but again, it makes him just look more like a now-privileged dick.
Overall, the show is amusing, but as a fresh take from someone who's delivered really genius-level comedy, it's disappointing. It felt somehow dated, even with the references to some current events. Don't get me wrong - I laughed. I really loved the bit about taking his son to see Kevin Hart. He shows both his aptitude as a parent and humility at his relative celebrity to Hart.
He also has a recurring series of stories about the four times he met O.J. Simpson, but that worked solely to transition him out of the other segments. He also fell flat when he complained about having to learn new pronouns for transgendered or other persons, in a way that was oddly xenophobic; this is what felt most anachronistic, really, about the set.
He still manages to land the delivery of his jokes, though, so even when I didn't love a particular bit I still chuckled at the way he said it. And he still does make incisive observations about race and racism. However, I think the line that hit me hardest was at the end of his drive about Bill Cosby. It was painfully funny, in that it hurt to laugh.
“I’m a 42-year-old black comedian. Obviously Bill Cosby was a hero to me. To think that your hero might have done something so heinous – it would be as if you’d heard that chocolate ice cream itself had raped 54 people. You’d say to yourself, ‘Oh man, but I like chocolate ice cream. I don’t want it to rape.’”
I'm not a black comedian, but I also loved Bill Cosby. I watched The Cosby Show but also listened to his records and watched the VHS of Himself with my father, and have so many of the bits memorized. One in particular is about Cosby as a child getting his tonsils out, and the naïveté of young Bill and the other patients thinking they've got it made, because when you get your tonsils taken out, "YOU CAN HAVE ALL THE ICE CREAM IN THE WORLD YOU CAN EAT." He goes on to say that for his first order of ice cream, he's not even going to eat it. "I'm going to smear it all over my body, and put a green cherry in my navel. I'll be the most BEAUTIFUL chocolate sundae you've ever seen in your life!" The hospitalized kids all sing a song about ice cream; "Ice cream! We're gonna eat ice cream! We're gonna eat it every day!" I, with my sister and my cousins and father, have sang that song probably hundreds of times in my life. I still think of it nearly every time I even talk about ice cream. And yet now, the ice cream is tainted. It's gone off. It leaves a bad taste in my mouth. So I felt that Chappelle's analogy was particularly apt. I love chocolate ice cream. I don't want it to rape. But it did.
So back to Chappelle. I wanted to be impressed, I wanted to be entertained. I didn't want his special to suck, and it doesn't. I didn't want it to be lame, either, but it was. But hey, Dave Chappelle is still rich, bitch.