A few years ago, I was hanging out with a comedian friend one night as he was waiting to go up for his set when the comic onstage told a joke about the homeless that got a huge response from the room. As the laughter died down, my friend turned to me and asked, “Are we still going after the homeless? Haven’t they been through enough?”

It was the most succinct way possible to deliver an important lesson about comedy: always punch up. So when I heard that Dave Chappelle was doing another bit about the trans community in his new Netflix special, I immediately flashed back to those words. And my worries about one of the all-time greats of stand-up choosing to punch down at a marginalized group only intensified when I heard that Chappelle’s bit included his take on trans athletes.

In Chappelle’s “Sticks & Stones,” the bit in question delivered exactly what you’d have expected him to say. Which is what makes it so disappointing.

Dave Chappelle is one of the greats. Which is why he’s held to a higher standard.

The trans athlete material is tacked on to the end of a larger section featuring Chappelle addressing the LGBTQ community as a whole (And yes, you may now assume the cringe position). It’s a quick digression but it still stands out for how pedestrian and derivative the material turns out to be.

As has been done numerous times by other far less talented comics, Chappelle starts by making something less than an original observation: namely, if men and women are essentially equal, there would be no WNBA. He then goes on to imagine what would happen if LeBron James “changed his gender,” picturing the Lakers forward joining the WNBA “where he will score 840 points a game.”

(EXTREMELY PICARD VOICE: Cringe position…engage.)

It all plays out like what would happen if Martina Navratilova showed up to an open mic. Even worse, the exact same “If NBA star (fill in the blank) were trans, they would overrun the WNBA” premise has been previously used by comedy titans like… Christian pundit Dr. Michael Brown. Such a dismissive stereotype and shopworn trope coming from any comedian would already be a letdown. The fact this is Dave Chappelle makes it exponentially worse.

“Wait…I’m telling a joke that was already done by a Christian radio DJ?…Hoo boy…”

Chappelle is one of the greatest comics to ever pick up a microphone and has set a standard for himself with brilliant performances from classic specials like Killin’ Them Softly. There’s good reason why legends like Chris Rock speak his name in awe. His body of work represents a volume of creativity that very few comedians can hope to match.

Despite all of this, Chappelle’s take on trans athletes essentially boils down to what would happen if a sentient human being thought Juwanna Mann was a documentary. In fact, from a comedy standpoint, it’s particularly damning that Chappelle couldn’t think of anything more interesting to say about the topic than simply repeating Juwanna Mann’s premise and passing it off as special-ready material. Can’t wait to hear his brand new bit on how crazy it would be if Snoop Dogg became an airplane pilot!

Pictured: NOT THE ACTUAL WNBA.

The WNBA, incidentally, does not ban teams from populating their rosters with trans women. So if Chappelle’s scenario of a team signing trans athletes and dominating the league was conceivable in reality, it would have happened already. I know that over-explaining a joke is an exercise in long-winded pedantry, but it’s worth it in this instance, to show why the LeBron line is a flawed premise.

To be clear, one of a comedian’s main instincts is when people tell them that they can’t joke about a certain topic, that only makes them want to dedicate more of their set to it. And that can be a very good thing — as long as it results in jokes that are thoughtful and well crafted. The problem is that when Chappelle talks about trans athletes and the trans community as a whole during “Sticks and Stones,” his jokes are neither.

But there’s something even more frustrating about it… in between the base-level transphobia, Chappelle has actually buried the idea for an infinitely better bit. While discussing his problematic relationship with the LGBTQ community, Chappelle sets up an act-out, pretending to be each member of the community traveling together in a car trying to get somewhere and failing because each one spends all their time sniping away at the others.

As a premise, it’s a subversive way of showing how the community can often be its own worst enemy, getting lost in surface level judgements and arguments that prevent them from actually going anywhere. In the hands of a skilled comedian, this could be a devastatingly funny and original piece of material. And Dave Chappelle is one of the most skilled comedians of all time.

Which makes it all the more unfortunate that instead of finding out where this premise could take him, Chappelle cops out with easy and insulting punchlines — the “gay voice,” pronoun confusion, etc. It all eventually resolves itself in the tired and overdone take on trans athletes mentioned above. The whole section comes across as a waste of potentially great material, all because Chappelle didn’t do the work necessary to make it into something more memorable.

For fans of Chappelle, there is still a bit of good news: once he finishes the trans athletes bit, the quality of “Sticks & Stones” picks up substantially, and the latter part of the special is a worthy representation of his talents. So if you want to be reminded that he’s still got the skills that brought him to this level of fame, skip over the first half and start watching at the 32 minute mark. It’ll be like screening a mini-Chappelle special and seeing him at something closer to his prime.

Because the first half of the special makes one thing clear: trans athletes put more effort into their craft than Dave Chappelle put into writing jokes about them.

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