In his new Netflix special, Chappelle is "proud of his trans jokes, dismissive of cancel culture, and defensive of celebrity status," says fellow comic Shalewa Sharpe. "Overall, he comes off as a very rich old man yelling at today’s kids to get off his expansive lawn. Why does Chappelle seem so out of touch? Yes, he’s wealthy enough to not have to mix it up with the hoi polloi, though I’m sure he’s appreciative of the dollars we fling at him for live performances. He’s not even that old — he just turned 46 on August 24. His chest hair is probably only now starting to gray. My friend recently mentioned on Twitter her surprise at Chappelle’s age. I tweeted back my theory that Chappelle is probably dealing with an unexpected aspect of middle age: the hardening of your worldview, for better or worse." Sharpe adds: "A midlife crisis isn’t just buying a ridiculous vehicle, pulling a muscle at the gym, or leaving your wife. (It also doesn’t only happen to men, Hollywood, but we ain’t got time for that.) It’s realizing that after 30 years of my being the Go-To Voice (and ten years of diminishing returns), the world has stopped listening. So when you speak confidently about, say, music or sports or dating based on the way it’s always been and a young person informs you of the way it is now, it can knock you back on your heels. A decision must be made: Am I in the mood to reflect and adjust, or am I going to dig in my heels because it’s what I’ve always known?"
Smart comedy can be shocking, but shock value comedy isn’t inherently smart: "So he said some things he wasn’t 'supposed to' say," says Tonja Renée Stidhum. "So what? Was there any added value to rehashing the same tired transphobic jokes other than sheer shock? Even his proposition to register all black people for guns to make a real mark on gun control wasn’t a wholly unique idea. Chappelle once expressed how uncomfortable he was when he realized white folks were laughing just a bit too hard at his blackface skit, and concluded that perhaps his attempts at challenging stereotypes failed and were simply reinforcing them. How can that same self-awareness implode into an ignorance cloud when it comes to transphobia, homophobia and sexual assault?"
Dave Chappelle's rants about how sensitive audiences have gotten exude not just irritation, but also fear: "He seems entirely uninterested in punching up—partly because it doesn’t seem that many people are above him anymore," says Hannah Giorgis. "The special’s few standout spots occur when Chappelle offers asides reflecting on his own wealth or his previous financial hardships. But, taken alongside the rest of his material, even these moments reveal the comic’s sense that everything could be taken away from him at any time."
Chappelle shows why we need some political incorrectness: "Does Chappelle actually believe" his controversial statements? asks Maureen Callahan. "Or is he baiting us into a larger conversation, one he addresses in the special, about cancellation culture, groupthink and reflexive outrage? The swiftness of our news cycle coupled with the toxicity of social media, which generates instantaneous moral outrage that brooks no dissent? Trigger warnings, safe spaces, the softening of public debate — what are we becoming? What are these things costing us? It’s a conversation we’re not yet having, because — as Chappelle predicted in the introduction to his set — fury would be the immediate response to his special, among both mainstream media and online scourges."
Chappelle is too obsessed with cancel culture to write good jokes: "One such bit finds him exploring the premise that if trans people feel they were born in the wrong body, couldn’t he feel born in the wrong race?" says Joe Berkowitz. "...Does Dave Chappelle possibly think that in a post-Rachel Dolezal world, nobody had dared explore the premise of transracial people before? Does he care? Plenty of beyond-mediocre hacks have mined this shallow vein over the past five years; they just neglected to throw in a staggeringly backwards Chinese-person impression to make the point. Hell, Jamie Kennedy made the same joke independently earlier this week (on Twitter). Congrats, Dave Chappelle, you’re exactly as edgy as 2019 Jamie Kennedy!"
Chappelle's trolling in Sticks & Stones is especially appealing to online trolls: "Sticks and Stones is mostly an hour of Chappelle trolling trans people, rape victims, gay people, and other hyper-vulnerable communities while defending famous millionaires," says Damon Young. "And something happened while watching it that has never happened to me while watching Dave Chappelle. I got up and did things around the house while it was still on. Not because of some deep offense, but because I was just bored with it. Defending the words and rights of powerful people is perhaps the most mundane and least transgressive thing an artist can do, and last night was trash pickup night, so I multitasked so I could get to bed at a decent hour. That said, there are also many who consider this to be one of his best performances. And among that group are trolls, professional bigots, white supremacists, Nazi sympathizers and more of the very worst white people; an adoration due to the parallels between their sensibilities and his."
The problem with Chappelle's views is there's a far-right element putting him on a pedestal as a face of its toxic ideologies: "And that’s what’s scary—the aftermath of this special is a growing allegiance from one of the most hate-filled sections of the internet and the country today," says Khal Pacino. "Chappelle might be speaking his mind, but those who are aligning with his views—or at least his swagger, and regurgitating his words—is what makes this a dangerous time. Adding insult to injury is that, with his check cashed and the conversation around his special continuing to swell, Chappelle is likely going to go back into reclusion, chilling for a bit before hitting the road to do it all again. We likely won’t get anything more from him about it until he starts back up touring."