Dave Chappelle Is Too Smart (And Lazy) For His Own Good
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Dave Chappelle performs at Madison Square Garden during his 50th birthday celebration week on Aug. 25, 2023, in New York.
I remember watching Dave Chappelle’s 2021 Netflix special “The Closer” the day it went live and thinking, with a smirk of excitement and intrigue on my face, “Yikes…this is gonna ruffle a few feathers.”
What I didn’t expect was no fewer than five straight weeks of tweets, angry think pieces and general division over the special, which courted an unprecedented degree of controversy over his jokes targeting the transgender community. (FYI, this isn’t an angry think piece, per se.)
Fallout from “The Closer” included a suspension of a trans Netflix employeeand a staff walkout from Netflix’s Los Angeles office.
My lifelong allyship didn’t douse my overall enjoyment of “The Closer,” and I defended Chappelle’s ability to deliver transgressive jokes in an incisive fashion, reminding everyone that it’s a large part of the reason he’s one of the greatest living comedians. I also told his detractors that the best way to take attention away from his special was to not talk about it at all.
As I watched “The Dreamer,” Chappelle’s latest Netflix special, that intrigue and excitement I had for its predecessor was replaced with a nagging feeling of boredom.
“The Dreamer,” which contains several jokes I heard when I saw him live in Chicago in September, starts off with a story that not even I can defend: It’s an obvious fuck you to all the souls who were excited at the prospect of Netflix closing its doors to him after the 2021 debacle.
Shortly after, he announces that he’s leaving trans folks alone (save for “three or four jokes”) to go after the disabled community because they’re “not as organized as the gays, and I like punching down.” Another wink-wink response to all his detractors who said that his trans jokes are, well, punching down.
The rest of the special had its funny bits but felt like not enough innovation; not enough of an attempt to improve on his craft to justify my time and energy. And that’s a crying shame.
The cachet he’s earned after 30-plus years in standup, several movie roles and one legendary sketch comedy show provides him the ability to deliver jokes that would get most younger comedians bounced out of the profession. The problem is that Chappelle is leaning a bit too heavily on that privilege, resulting in less creativity and more shock for the sake of shock value.
Chappelle is organically funny, so his routine in which he mimics a disabled fan upset that they won’t hear trans jokes will at the very least elicit uncomfortable chuckles. But it doesn’t feel anywhere near as ingenious as his “How Old is 15 Really?” routine ― arguably the only funny bit in comedy history about statutory rape ― from his 2004 special, “For What It’s Worth.”
"It’s hard to suggest Chappelle hang it up when he still fills stadiums," the author writes.
But Chappelle is not alone. He’s moving like many other comedians of a certain era: He’s growing increasingly out of touch with an evolving society ― and comedic landscape ― that has rapidly diminished space for comedians whose routines are stuck in the wild, wild 1990s. I’d argue the same thing is happening with Chris Rock, another living legend whose 2023 Netflix special “Selective Outrage” is arguably the least funny and most out-of-touch of his oeuvre.
Like Rock, Chappelle also makes a point to remind us that he’s richer than us, and thus above our criticisms ― arguably a profound flaw in a genre that champions relatability. This was never more obvious than when Chappelle mind-bogglingly brought the despised Twitter ruiner Elon Musk on stage during a December 2022 show.
When the crowd booed Musk, Chappelle threw a shot at “the poors” in the audience. These are the same people he’s always expected to defend him when he told the Comedy Central overlords that he wouldn’t accept their money to bastardize “Chappelle’s Show” ― a story he shares with us often.
Chappelle is in that space occupied by many creative legends whose careers have more yesterdays than tomorrows; his Hip-Hop analogue in this respect is Eminem. Inarguably one of the greatest rappers of all time, Em is still making music well past his prime but takes it very personally when he’s criticized for missing the mark. Chappelle acts cavalierly, but boy does he care. And it doesn’t appear that he’ll hang up the mic anytime soon.
In contrast, Eddie Murphy ― who said things in his 1980s routines that not even Chappelle could get away with today ― hung his standup jersey in the rafters decades ago and seems reluctant to pull a Michael Jordan-Washington Wizards on the masses. Not a lot of room for cancellation when you’re only dropping Christmas family films on Netflix.
Of course, it’s hard to suggest Chappelle hang it up when he still fills stadiums. And though Netflix doesn’t release viewing numbers, it’s a safe assumption that they view Chappelle as a golden goose worth whatever headache they get on social media. Folks are still watching and talking about “The Dreamer,” and think pieces (like this), good or bad, will send viewers flocking to the special and continue securing him the bag. Who’s to argue with success?
I don’t think Chappelle is actually transphobic or antisemitic or ableist. As such, I don’t want to see his career end ― as a fan, I want to see him evolve. But as long as he has his fans and big bags on the material he’s doing now, I’m afraid his legacy will have the asterisk of easy layup laziness.
And I’m not sure that’s worth the freedom he desires.
