In private circles I can be a pretty funny guy. But I learned the hard way that I have neither the creativity nor the courage to be a stand-up comedian. The one and only time I took my “talents” to the stage I bombed an ‘Open Mic Night’ so badly that I decided I’d leave stand up to people better suited for the rigors of that craft. Call me a quitter if you like, but I discovered quite quickly that I definitely preferred my heart beating on the inside of my chest. Partly due to that harrowing experience, I sincerely admire those that possess the gift and the grit to master the game. In my book, that is pretty damned close to qualifying as a super-power.
I hold in especially high regard the precious few that actually have something of substance to say to their audience while delivering the laughs. Few would even bother denying that some truly exceptional philosophers have delivered their prized wisdom wrapped up in a killer punchline. The late George Carlin was probably the greatest of all time in that regard. But Dave Chappelle is right there with him.
Despite my own shortcomings as a comic, my judgment on the subject is about as sound as you can find anywhere. As an avid consumer of the artform, I understand the one simple rule of comedy success well enough. We all do, and it is this: Just be funny. It does not matter if your comedy is offensive, banal, unoriginal, or asinine. If a critical mass of people find your routine to be funny, you will be successful. And Dave is one of the most successful comedians of all time.
I remain in the shrinking chorus of commentators who still thinks of Dave primarily in terms of his work when the discussion swirling around him was his status as the sharpest and most insightful comedian to hold a microphone since Richard Pryor. But shit happens; and in this case that ‘shit’ was a peculiar fixation with poking the LGBTQ community in the eye with a stick. I still have great appreciation for Dave, but I can freely admit that he fell victim to the reflex that so many good brothers do. To wit: It is not enough for us to just be right in a stance we take; we have to be GOD-DAMNED right. And that is why Dave fell into this weird place in his performances where he seemed to be prioritizing slapping his detractors across the face with his microphone over making his audience laugh. That reflex can pose a problem when your detractors are NOT members of a marginalized and vilified minority group, so you know it’s a five-alarm-dumpster-fire when they are.
But way before all that went down, Dave presented the broad racial dynamics of modern America better than any other comedian I have ever heard. It was a pitch-perfect combination of irreverent humor and illuminating insight and people of good conscience from every background would do well to revisit it now. America is seriously at risk of burning to the ground after this next election largely due to its failure to deal effectively with matters of race. But if a critical mass of engaged citizens takes a pause from the non-stop outrage of social media, cable news, and corporate propagandized news coverage and jumps online to Comedy Central or Netflix to explore and enjoy The Racial Draft sketch from Season 2, Episode 1 of Chappelle’s Show, which aired originally on January 21st of 2004, we might still extinguish the blaze before it extinguishes us.
Dave was at the peak of his creative powers when he wrote and starred in this timeless sketch for his monster surprise hit variety show. His distillation of American race relations was perfectly original, which is very hard to do since race has always been one of the top two or three subjects of comedy routines, for Black comics especially, as far back as most of us can remember. In The Race Draft sketch, Dave reframed racial dynamics as a sports league competition rather than a fight for dominion or survival.
And it worked beautifully; mainly because the overwhelming majority of us are NOT in a fight for our very lives on a daily basis because of our race. Not only that, for most of us, our race operates in sneaky and subtle ways that we tend to tune out. Of course, back then Twitter hadn’t hijacked the minds and amplified the mouths of the loudest and most obnoxious players on the field, but that is a story that has been well-told many times over. Dave’s set up still holds true to form and has aged perfectly well.
Dave had Bill Burr (a comic genius in his own right) join him in a satirical bit as they portrayed sports commentators covering the “First and Maybe The Only Racial Draft: Live from New York City!” The fact that it mocked the fundamental stupidity of American sports media and how seriously it takes itself was a nice opening pitch. Not just because it was funny, but because it helped introduce the first stroke of genius of the sketch. The depiction of biased media coverage in service of an agenda and how dangerous and damaging it can be depending on the treachery of the man holding the mic was the perfect setup. Dave and Bill engage in faux-friendly sparring over the upcoming draft choices of various public figures with racially or culturally mixed backgrounds by delegations representing The Blacks, The Whites, The Jews, The Asians and The Latinos.
Up for grabs were superstars like Tiger Woods (Black folks got him), Lenny Kravitz (Jews got him), Colin Powell (White folks got him), and RZA of Wu Tang Clan (Asians got him). Dave and Bill commented on the implications for the stars new singular identity, and intermittently cracked wise about the proper draft positions of O.J., Oprah, Halle Berry and Mariah Carey. And it was perfectly satisfying comedy. The actors leaned so hard into racist stereotypes that it was impossible for any sane and reasonable viewer to take personal offense. The joke was on everybody and everybody got it. It is one of the sketches that helped propel Dave into super-stardom so that his catch phrase “I’m Rich Biatch!” could manifest into his permanent reality. So much so that any future efforts to “cancel” him would only make him more powerful than he was before; even if it made him noticeably less funny.
After the laughs finally slow down, the critical thinking can pick up. We can stop and consider the implications of the sketch and the reality it reflects:
A draft only exists when you have a league of competing teams. And if you have a league comprised of competing teams, those teams are going to… compete. And in every competition, the score is kept to determine who wins and who loses, and by how much. Consequences flow from how well or how poorly a team performs in the competition. America IS that competition.
And the consequences that flow from the final score are heavy and hard, regardless of the crooked referees or the hostile stadium endured by a visiting team. While everything is not necessarily a zero sum game, the spoils of victory are distributed without equity as a consideration. That has never been a part of the game in American race relations.

No matter what our individual attributes or achievements may be, each of us is a part of a team and the performance of that team is a reflection on us. Fair or unfair. For better or worse. That famous “content of our character” line was one of MLK’s finest, but that was high-minded poetry, and we are all living in the low-lands of prose.
Chappelle’s ‘Race-Draft / Racial-League’ reality is one that we on the progressive end of American politics have worked very hard to wish away. Black politicians especially. But the foundation is too sturdy and the commitment too stubborn for their weak wishes to mean anything. That is why we attempt in error to sell race-neutral solutions to problems that are specifically driven by racial inequity. We obscure the plain truth that, because of the great Race-Race, when our team gains any advantage, other teams necessarily lose ground at the same time. Whether an advantage is large or small, our efforts to obscure the full impact only weakens our resolve to play our best game when we are on the field.
And that playing field is the American marketplace. The Black team in particular has had a steep uphill climb in inclement weather in running our race. And even the most fair minded of our competitors doesn’t really give a damn.

A better way to put it is to say that there is a significant number of White men out here who actually don’t mind seeing a Black man get ahead; they just don’t want to see that Black man getting ahead of THEM. Now is such a man wrong for that? Not really; not in a competition he’s not. He is about winning the race himself and will use every means necessary, fair and unfair, to trip up anyone who threatens to best him. His insistence on lying about his motives draws well deserved ire, but the motivation itself stands on its own in this context. Frankly, any other competitor who does not share that motivation is a fool destined to lose.
Despite having some outstanding, all-star, individual players on this team, as a whole our team has struggled to gain ground on our competitors in every metric that measures marketplace performance. While we’ve gained in education, we’ve stalled in net worth and property ownership relative to our White, Jewish and Asian competitors. The numbers speak for themselves and tell an ugly story. No net Black gains whatsoever in 40 years?! Don’t shoot the messenger, which happens to be the Brookings Institute. They just did the math.
Western capitalism stands on the principal that one participant’s loss can always be readily converted into another participant’s gain. It almost always is. So it goes with racial groups. When Native American Tribes secured their rights to casino gambling operations around the country, those were casino operations that were no longer available to any non-Indigenous person. But it went over well, and it should have, because it was a fair and just policy. It went some distance toward rectifying the treaty violations and war crimes committed by the United States government.
That is why New York gubernatorial candidate Cynthia Nixon proposed carving out the newly legalized cannabis industry for Black New Yorkers during her 2018 campaign as redress for past injuries inflicted by the state’s economic discrimination and exclusion. But we can be an emotional bunch sometimes and for some dumb ass reason actually took offense to her idea.

And in so doing, we missed a moment that could have permanently changed the game, or at least reframed and reopened the debate about the game. Now that is a twenty-one billion dollar a year business and, like every other business that does not involve entertaining crowds, we own and control almost none of it.
And the hardest truth of all is that there is no opting out of this game. Like it or lump it, the minute you hit the American track-and-field you are on a ‘team’ based on the racial identity the world around you perceives. Your feelings about the team you are on are probably at least a little bit complicated and may absorb more of your mental bandwidth than you’d prefer. Your feelings about your team may vary as widely as the searing hate that Clarence Thomas and Candace Owens have for their team, versus the irrational unconditional adoration that a Samuel Alito and Megyn Kelly have for theirs. Most of us fall somewhere between those cartoon villains.
But regardless of where you fall on that spectrum and as unfair as it is, everything that you do, every step that you take, and every representation that you make, will be attributed by those who bear witness as a representative act that bears on the perception of your team. And that perception, standing alone, is leverageable in the marketplace. Progressives have tried very hard to lie our way out of this reality, both to ourselves and to others, but the natural human reflex to generalize is hard-wired. The more advanced and self-aware players understand the power of that reflex and work to account for it in how we play the game. But it’s always there.
And because we are aware that it’s there, we can account for it quite simply by playing the game hard, playing the game clean, and playing the game to win. Doing your individual part for your team is your main responsibility.

Fortunately, you get rewarded for running a winning race even when many on your team are not. Just always help a teammate when you can, and never kick a teammate when they’re down. And keep your head up, because somehow we keep staying in the race and busting our asses to make up ground.