How I lost my respect for Dave Chappelle

A prophet calls from grace

I did a wedding once where I called Dave Chappelle a prophet, and I meant it when I said that. Chappelle has always has an unique way of approaching the truth, especially when it relates to race relations in the United States. With humor and humility, Chappelle could say things no one ever would and deliver messages that seemed to transcend the discourse and land us on the truth. I may have been overstating it when I named him as a prophet, but there were many moments where Chappelle taught me something new, often with a spiritual quality, about the world I was in. I admired Chappelle greatly.

But despite his brilliance, and I mean that, in his latest Netflix specials, though they have moments of precision (just a few), Chappelle navigates territory—both related to women and LGTBQIA folks—with the confidence of a celebrity, fearless of consequences, and ready to say any offensive remark he made was just a joke.

Chappelle made sexist, homophobic, and transphobic “jokes” in his specials, perhaps ones that would have worked in his early-2000s career, but decidedly fell flat in his specials in the late 2010s and early 2020s. His most recent special was full of more of offensive humor, but declaring it as his last special, Chappelle moved to defend himself and his behavior, arguing he was subject to hysteria, criticism from people who didn’t actually consume his shows and specials. He argued he was a victim of soundbites, and not sound criticism.

Chappelle’s humor didn’t age well

Since I previously objected to the bigotry in Chappelle’s humor as of late, I was not surprised to hear that his latest special was littered with the same material. Saeed Jones wrote, “I felt like I’d just been stabbed by someone I once admired and now he was demanding that I stop bleeding.” Roxane Gay said, “The self-proclaimed ‘GOAT’ (greatest of all time) of stand-up delivers five or six lucid moments of brilliance, surrounded by a joyless tirade of incoherent and seething rage, misogyny, homophobia and transphobia.”

I watched the special myself so as not to be subject to Chappelle’s critique of his detractors. I watched the 72-minute special, and honestly barely laughed, and the moments where Chappelle usually shines—when he says the truth no one is willing to say—were flat. My admiration grew for Chappelle when he would tell hard truths about American race relations. Even his recent 8:46 special spoke powerfully about the death of George Floyd. It shows Chappelle at his best, at his most prophetic, when he’s speaking to his audience about things he knows based on his experience with humor, charisma, and with power.

The “truths” Chappelle offers in his latest special, titled “The Closer,” do move us to his lived experience as a black man, but consistently at the expense of other minorities. Chappelle claims that his jokes are not at their expense, but rather at the expense of white people. Chappelle defends his bigoted humor as not actually being bigoted, with the sort of entitlement that, frankly, you might expect from white male stand-up comedians crying about their free speech (see here, Emma Green interviewing the lowlifes from The Babylon Bee). Not only is his comedy low-brow and not very creative, but his defensiveness also makes it even worse. For me, Chappelle moved from a creative, sometimes genius, stand-up comedian, to one who could not adapt to a new generation or to new truths offered to us by listening to new voices. Chappelle advocated for a new world, and when that world came, he could not move out of his old one.

No longer could, or should, the dialogue around race relations be only a matter of race, but rather, one that intersected with gender, sexuality, ability, class, and more. Intersectionality may not make for good comedy – though I think you can write good comedy that is not offensive – it is an essential aspect of listening to marginalized people.

Chappelle reminded me of how our elders can disappoint us

What was disappointing to me as a fan of Chappelle’s is that the man who taught me so much refused to learn something new. Dave Chappelle is a painful reminder of what it feels like when people you admire fail to continue to develop and, instead, regress. It’s a hope killer when our elders do not show us how to grow, and learn, and change. Keep listening to young people, and let them lead us.

Chappelle refused to learn and adapt to a new setting, but in fact, defended himself, and maligned his critics. He exploited his personal relationships to defend himself against transphobia. A shadow of his former self, he was hypocritical to the extent that I wondered whether he was ever funny, or even that profound. It’s painful to see someone you admire fall from such grace. Chappelle critiqued his detractors as overly sensitive, but it was he who was the overly sensitive one, unable to take constructive criticism, and defending his fragile self.

Like I said above, it’s a hope killer because we all want to believe we can change and grow. Our elders have an opportunity to show us how to do that. When they double down on their mistakes, when they don’t apologize, when they defend themselves, they don’t show us how to grow and change. They, further, disrespect those they taught and they silence those who might teach them something new.

I admit I suffer some cynicism and despair at wondering whether my elders can change, whether they were mentors, my parents, or even celebrities like Dave Chappelle. I long for the example of someone who learned to grow wiser, instead of turning into an old fool, as Chappelle has demonstrated. The man did say he would take a long break from comedy, and perhaps that break will be an opportunity for growth. I hope he returns as a wise man, one with the wit and cleverness that I saw in my youth, and not a bumbling idiot.

One Reply to “How I lost my respect for Dave Chappelle”

  1. I am so glad someone else sees what I see!
    I also once reveled in Dave Chapelle’s brilliance, not just because he was a genius among comedians, but also because he seemed an astute sociologist, psychologist, philosopher, historian, and poignant storyteller … but also because he was an regular fellow human-being also struggling through this emotionally confusing and often tortuous journey we call “life”.

    Yet over the last year or so I see a painfully disappointing shadow of the “prophet” Dave once was – now he’s just another predictable “celebrity” with too much money who’s too impressed with his own power and appeal to have any actual WISDOM or EMPATHY for anyone or anything he doesn’t personally understand. Telling all white women to “just shut the fuck up”, denying the trans community totally, and having a judgmental mocking of Anthony Bourdain’s suicide are all the examples anyone who’s never heard of Dave Chapelle should need to decide whether or not to bother watching his next “performance”.

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