Dave Chappelle Is Too Smart (And Lazy) For His Own Good

I remember watching Dave Chappelles 2021 Netflix special The Closer the day it went live and thinking, with a smirk of excitement and intrigue on my face, Yikesthis is gonna ruffle a few feathers.

What I didnt 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 isnt an angry think piece, per se.)

Fallout from The Closer included a suspension of a trans Netflix employee  and a staff walkout from Netflixs Los Angeles office .

My lifelong allyship didnt douse my overall enjoyment of The Closer, and I defended Chappelles ability to deliver transgressive jokes in an incisive fashion, reminding everyone that its a large part of the reason hes 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, Chappelles 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: Its 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 hes leaving trans folks alone (save for three or four jokes) to go after the disabled community because theyre 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 thats a crying shame. 

The cachet hes 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 wont hear trans jokes will at the very least elicit uncomfortable chuckles. But it doesnt 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 Its Worth. 

But Chappelle is not alone. Hes moving like many other comedians of a certain era : Hes 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. Id 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 hes 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 hes always expected to defend him when he told the Comedy Central overlords that he wouldnt accept their money to bastardize Chappelles 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 hes criticized for missing the mark. Chappelle acts cavalierly, but boy does he care. And it doesnt appear that hell 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 youre only dropping Christmas family films on Netflix. 

Of course, its hard to suggest Chappelle hang it up when he still fills stadiums. And though Netflix doesnt release viewing numbers, its 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. Whos to argue with success?

I dont think Chappelle is actually transphobic or antisemitic or ableist. As such, I dont 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 hes doing now, Im afraid his legacy will have the asterisk of easy layup laziness. 

And Im not sure thats worth the freedom he desires.