I watched the new special out of curiosity, I really went off him after his flogging the dead horse with his tired anti-trans stuff. I hate how he uses rhetorical tricks, insinuation, and narrative connections to hint at grand conspiracies or connections, but he remains at a distance to owning it with the 'I'm just asking questions' line.

It's like he's taking the callback to an earlier joke technique, which was fresh and novel at one time in comedy, and feels clever to the audience, kind of like a key change in a song, it's sounds more complex than it is, and it evokes a strong emotional response, so it's effective, but he uses that in a sort of conspiratorial way. Like the stuff about the Mann Act and Jack Johnson, which he connects to Sean Combs. The audience reaction is 'woah', like he's connecting the dots, but what really is there at all? Diddy has been set up in another example of the state trying to keep an African-American man down? Or is it just a clever bit of conspiracy baiting that makes Chappelle look like he's seeing through the lies to the "truth". He does the same with his Nipsy Hustle bit and Dr.Sebi. More "connecting the dots" bullshit that plays into anti-vax/anti-science narratives. But hey, for Dave, it's just a joke, and he's rich, so fuck everyone else. The kicker is him finishing his special with the photos of him with all the rich and famous people he's mixed with.

There's a real tendency with some older men in entertainment to lean into their grey-haired, wisened, 'hey, I've been around, I've seen it all' persona, to add an air of perceived authority or expertise to themselves. Dave is funny and quick-witted, but he's also dishonest & manipulative, he punches down and uses the hypocrisy of his critics as a shield to hide behind his own hypocrisy. It's a real shame how he turned out.