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Dave Chappelle refuses to evolve

The legendary comedian’s back with a new set, ‘The Closer,’ and largely the same bag of tricks

They say that pride comes before the fall but it’s jealousy that more times than not leads to war. And that’s currently what Dave Chappelle finds himself in. Early on in The Closer, the legendary comedian’s final Netflix stand-up, Chappelle brings up DaBaby and how the rapper flew way too close to the sun with his anti-gay tirade at Rolling Loud.

Chappelle says society cared more about what was said to the LGBTQ community rather than what was done to a Black man. It is true that DaBaby, in 2018, shot and killed a 19-year-old man at a North Carolina Walmart. Yet, what Chappelle failed to mention was that DaBaby has always claimed it was self-defense (the victim’s family refutes that).

But Chappelle took it a step further: “I’m jealous. I’m not the only Black person that feels this way,” he said. “We Blacks, we look at the gay community and we go, ‘God damn it! Look how well that movement is going!’ And we’ve been trapped in this predicament for hundreds of years. How the f— are you making that kind of progress?”

The flaw here is that despite Chappelle claiming that he’s talking to the white community, he failed to offer any context to race and sexuality — in particular, how the Black community is grappling with acceptance.

That’s the maddening part about it all, because the comparison just doesn’t land, nor is it accurate. Neither does the assertion that Black folks would’ve been free a century sooner had there been “baby oil and booty shorts” — as if same-sex relationships only began in the 20th century.

I’ve followed Chappelle for the last quarter century, which is why it’s so disheartening to see him plant a flag on this hill. Chappelle’s decision to pursue the always-flawed game of “oppression Olympics” between Black folks fighting for liberation and the LGBTQ community’s fight for equal rights is inaccurate. Black LGBTQ folks have been foundational elements of both movements — and continue to be. Chappelle mentions he misses the days of Stonewall, referring to the uprisings in June 1969 after police raided the Stonewall Inn, a gay club in New York. Helping lead the charge in those demonstrations were two Black LGBTQ forces in Marsha P. Johnson and Stormé DeLarverie. And then of course there are people such as author Audre Lorde, civil rights activist Bayard Rustin and, one of Chappelle’s biggest influences, James Baldwin — all of whom saw the value of their race and sexuality and how the fight for both was critical to their survival and future generations.

In The Closer, Chappelle recounts a story about having the cops called on him by a gay white man in Texas. “And this, the thing that I’m describing, is a major issue that I have with that community,” he said. “Gay people are minorities — until they need to be white again.”

Chappelle is addressing white people, but he does very little to protect the queer and transgender Black men and Black women who live in both worlds and fight both fights. At The Closer’s conclusion, Chappelle pleads for the LGBTQ community to stop “punching down” on his people. “Punching down,” in essence, is what Chappelle has been doing the last several years to a community that includes people who look like him. Even if they aren’t his intended targets, that’s nearly unforgivable to a man who says he fights for Black folks every day.

When Chappelle returned to the national stage in 2017, it was clear that much had changed since he last filmed his heralded sketch comedy show. George W. Bush wasn’t president any longer. America’s first Black commander in chief had come and gone, replaced by a reality TV star who lived in the White House in part due to America’s fear of a Black planet. Gay marriage was expanded to all 50 states. “Don’t ask, don’t tell” was repealed. Black Lives Matter happened. The #MeToo movement was exposing the depths of sexual assault and rape inside the entertainment industry and out of it. Voices that had long been overlooked or silenced were now boldly fighting for the right to be heard — and live.

On the surface, it was a climate ripe for someone like Chappelle, whose vivid storytelling and gut-wrenching punchlines separated him from any other comedian. But with each passing Netflix special, it’s become quite clear that Chappelle has made LGBTQ+ people a larger focus because he himself has not moved on.

Much of the recent critique of Chappelle has been about how he addressed the transgender community. “These n—as want me dead,” he claimed. Anyone who has studied his performances, Chappelle reasoned, would know he never had beef with the transgender community. This might’ve made some sense had he not claimed himself to be “team TERF” (trans-exclusionary radical feminist) and balked at the notion of transgender women being real women just moments later.

“If you listen to what I’m saying clearly, my problem has always been with white people. I have been arguing with the whites my entire career,” Chappelle stated. “Just when I thought I had you guys on the ropes, you changed the rules.”

That is true, to an extent. Chappelle’s major antagonist/muse during his time in the spotlight has been breaking down the gross miscarriages of justice carried out by white people on Black folks. And it’s no secret that white supremacy exists in the white queer community.

Yet it’s also true that, on all of his specials, Chappelle had the opportunity to highlight the violence inflicted on the Black transgender community and largely dropped the ball or didn’t care to dribble it in the first place. The same Black community Chappelle pledges himself to is the same community that rallied around the murder of George Floyd by a police officer and made it an international cause. That included the very same community Chappelle claimed DaBaby punched “right in the AIDS.” And, in so many ways, it’s the same community that drops the ball whenever it — not just Chappelle, either — doesn’t ride for the killing of Tony McDade, a Black transgender man killed by police just two days after Floyd, or the death of transgender activist Monica Roberts. That type of recognition from a figure as influential as Chappelle sometimes helps shift entire narratives.

Because that’s exactly what Chappelle did by telling the touching story of his friend, a white transgender woman named Daphne Dorman, who ended up dying by suicide days after being dragged on Twitter for defending Chappelle’s stance toward the transgender community. It was frustratingly hilarious to hear Chappelle say repeatedly how she bombed while opening for him in San Francisco. He humanized her in a way that made every joke he told about her feel less invasive. Eventually, it was Dorman who told Chappelle, “I don’t need you to understand me. I just need you to understand that I’m having a human experience.”

The frustrating part is she was right. But it wasn’t just her being transgender, it was Chappelle humanizing a white transgender woman when that’s all the conversation has ever boiled down to for years within the Black transgender community: that desire to be seen as human and not a source of ridicule.

Earlier this year, comedian Katt Williams spoke poignantly on The Joe Budden Podcast about cancel culture, in particular, a comedian’s ability to apply his art to the times instead of forcing the times to accept his art. There’s a quote that stuck with me and influences how I view Chappelle now.

“Look, if these are the confines that keep you from doing the craft God put you to, then it probably ain’t for you,” Williams said. “I’m saying your job as a comedian is to please the most people with your art. So if you want to offend somebody, nobody took those words away from you. Dirty b—- ain’t been taken away. You can say that. But don’t call somebody this word when you know this affects all these people. Don’t use the R-word when you really mean people on the spectrum. Don’t say this word instead of saying ‘autistic.’ ”

That’s the most frustrating reality about The Closer. The frustrating reality about the last half-decade for Chappelle, really. He’s not a history teacher or an activist, but there is a responsibility that comes with a tongue as mighty as Chappelle’s. When he talks, he has the power to shift discussions with that wicked combination of storytelling and delivery. And, at least in terms of this discussion, he’s done the complete opposite.

Chappelle says The Closer is his last stand-up for some time. He says that he’s done addressing the LGBTQ community and that whenever he does return everyone will be laughing together. In the days since watching the Netflix special, I’ve asked myself this question a thousand different ways: Can Dave actually pull that off? The answer is, I don’t really know. Yet, there’s one thing for certain. Whenever he returns, the world will be different from what it is now. We’ll all just have to wait and see if the same happens for Chappelle.

Justin Tinsley is a senior culture writer for Andscape. He firmly believes “Cash Money Records takin’ ova for da ’99 and da 2000” is the single most impactful statement of his generation.