When Dave Chappelle Schooled Negrodamus

Nostradamus was a 16th Century astronomer, physician and world-renowned seer. In the 21st Century, we don’t really have seers, we call them con artists. But the premise of being able to perceive things other people could not quite grasp led to a famous bit on Chappelle’s Show called Negrodamus, where difficult questions were asked of the esteemed soothsayer by the studio audience.

At the time, Wayne Brady was already a famous actor, known for G-Rated Comedy and easy listening R&B. One day in the studio audience, a large Black Man in a tight turtleneck with a bald head and perfectly sculpted goatee rose to ask Negrodamus a question weighing heavily on his mind,  “Negrodamus, why do White People like Wayne Brady so much?”

Wearing a straight face underneath a maroon hat with a purple plume, he answered, “White People like Wayne Brady because he makes Bryant Gumbel look like Malcolm X.”

In his response, Negrodamus indicted the Blackness of two men he didn’t know. It begs the question: did he have the right? I guess it depends on how you feel about Paul Mooney. He was a writer for Richard Pryor and Redd Foxx, he was a beloved comic, some would even call him “a comic’s comic.” But do those credentials give him the right to make Wayne Brady feel bad about himself? 

Wayne Brady didn’t think so.

He made it known.

Negrodamus was played by Paul Mooney on Chappelle’s Show. So you could blame Paul Mooney, but if you dig a little deeper then you have to admit the buck stops with the show’s namesake, Dave Chappelle. This controversy happened to strike in the 3rd act climax of the 2nd season. Dave Chappelle could easily have blown it off but instead he did something truly remarkable: he reached out to Wayne Brady, he listened, acknowledging the pain.

You have to keep in mind, there were only 2 seasons of Chappelle’s Show, 12 episodes per season, 24 total episodes. At the time of its airing, Dave Chappelle had no idea the show would go on to become one of the most revered sketch shows in the history of comedy. He was still new to being famous. If you re-watch the 1st season, you can see Dave surprised each week when his show hadn’t been canceled. This wasn’t a bit, he was actually wrestling with new fame and the unrelenting pressure of network executives threatening to cancel his show.

Dave wrote a bit where he quits the show and turns it over to Wayne Brady. In the episode, there’s a bit where Dave and Wayne hang out, going for a drive, as “Black Actors,” celebrating the idea of being peers. It takes on the feel of a notorious good-cop bad-cop movie called “Training Day,” where Wayne Brady is the cynical veteran cop and Dave Chappelle is the naive neophyte. At one point, Dave says he needs to stop by an ATM to get some cash and so Wayne takes it as an opportunity to pull over. He calls out to a group of prostitutes, summoning them to his car. He demands their cash, like a pimp in charge of the corner. One of the prostitutes is short on money and Wayne Brady says something legend has it he did not want to say, but the staff on Chappelle’s Show somehow convinced him to say it anyway. This is what he says…

“Is Wayne Brady Gonna Have To Choke A Bitch?”

It ran so against character, Wayne Brady touched the elusive mantle of “Blackest Man In America,” breaking the Uncle Tom curse of Negrodamus.

At the time, Dave Chappelle was new to fame, he was still familiar with the feelings of being ignored or overlooked or easily discounted or cast aside; in other words, he knew what the rest of us feel like pretty much every day of our lives. But once you’re famous, that all changes. And if you’re famous for as long as Dave Chappelle has been famous, a Mark Twain Prize Recipient, the self-described GOAT – Greatest Of All Time – how do you remember what it feels like to be afraid?

I’m not talking about being afraid of bombing, that’s part of the gig and anyone who’s been on stage long enough will tell you, the bigger the bomb you’re facing, the bigger the laugh you’re about to uncover. I’m talking about the fear of being humiliated, the fear of your pain being ignored, the fear you don’t matter, the fear your desire will be turned against you, the fear you do not have the right to expect safety when you walk out of your home.


In 2006, Dave Chappelle ended his show. He was so tied to the emotion used in crafting the jokes, he could actually hear the tone of how the laughs were landing. The shame underneath the premise of a particular bit about a pixie in blackface who’d pop up anytime a person felt the humiliation of racism didn’t sit right, the laughs were wrong. He could no longer distinguish the difference between satire and abuse. So he did something impossible to imagine in a culture obsessed with money, he walked away from $50 Million Dollars! That must have been terrifying! Who walks away from that kind of money? He had no way of knowing he was walking into a world where, in 2016, Netflix would pay him $60 Million Dollars to deliver 3 comedy specials, a world where, in 2021, Comedy Central would succumb to public pressure, paying him for money owed, kneeling at the Altar Of Chappelle. Back then, Netflix didn’t exist. Back then, Comedy Central had their hands on all the levers of power, using a team of lawyers and legal loopholes to cripple the young comic, using the press to call him crazy for ending the show and stealing the rights to his name. 

I think about that guy right now, in the shadow of The Closer, as the Trans Community cries out to be heard, I find myself asking where’s the guy who saw beyond Negrodamus? In the middle of The Closer, Dave Chappelle calls himself The GOAT, and in that moment he wasn’t a comic – he was a rapper – it wasn’t a punchline, it was a brag and maybe when you’ve been famous for too long, you get lost.

I watched The Closer 4 times, laughing at the jokes. A friend of mine, Lex, is Trans. I wanted him to watch the special so we could talk about it. But he refused, he’d heard enough about the special to know he didn’t want to bruise his knees crawling around in unkindness looking for a laugh. I told Lex the joke Dave told about his friend Daphne, a Trans Woman who threw herself off a building and in so doing, Dave joked that she died like a man. Lex put his hand on his forehead and shook his head from side-to-side as he massaged his temples.

“You were called a horrible name when you were a child, Greg. Your skin was dark and your hair was curly and in the White Community you were raised, many thought you were Black and so they called you Nigger. It was horrible! And it happened! To you! And it happened to you over and over, for years and years. You were a kid when it happened and so you thought, like a kid, it was never going to end. Then, later in life, when you had your livelihood stolen from you, when you were terrorized by Neo-Nazis for speaking up after Charlottesville, when you were terrorized by thin-skinned White Nationalists, offending them with a Tweet after the Las Vegas Shooting, you had dreams about hanging yourself. You were so freaked out about how unfairly you were being treated that your subconscious wanted out. But you survived. You had the internal strength to persevere. You didn’t hang yourself. But what if you weren’t strong? What if you were too broken to navigate the pain? What if you hung yourself? What if I decided, at your funeral, to tell a joke. To tell this joke,” Lex said, clearing his throat. “We’re all gathered here today to mourn the loss of Greg. A beautiful soul. Kind. Caring. Unlike anyone I have ever known. As many of you might know, in Greg’s youth he was a dark skinned kid in a Lily White Community and so he was called Nigger. It was a horrible thing that happened to Greg but throughout his entire youth he was called Nigger. He was called Nigger by his brother. He was called Nigger by his childhood friends. The adults ignored it and so even at sleep away camp, he was called Nigger. It was a nickname he couldn’t escape and so I guess it’s only fitting that Greg ended his life by hanging from a noose.”

I laughed. But is it funny? And even if it is funny, is it the right place to use tension to land a joke, at the expense of someone who took their own life.

I’ve been thinking about that joke for a couple months, wanting to write something about Dave Chappelle and The Closer, but not sure how. Finally, I was talking to Lex the other day about a book he read to his students when he was still teaching 5th Grade. The book is called “Roll Of Thunder, Hear My Cry” by Mildred D. Taylor. It has language in the book which is used to humiliate Black People. Lex wanted to read it to his students. But before he did, he reached out to all of the parents to make sure they understood what he was doing, why he wanted to do it and most important of all, he reached out so there would be no surprises.

To honor this gesture, I called Lex to ask him a few questions about what he was hoping to teach the kids, what he was trying to convey to the parents and what it is about the language of Mildred D. Taylor worthy of going to bat for.

I started by asking Lex about the conversation he had with the parents.

“I said I wanted to read this book – it was a Newbery winning book – it was written by a Black Woman author named Mildred D. Taylor. She had a very powerful voice and looked at things from a unique point of view. But the problematic piece for me was it had The N-Word in it and I’m not comfortable saying that word but I’m less comfortable rewriting history and rewriting this author’s words. So I intended to read the words as written unless that was problematic for them. And if it was, I completely understood. Well, I don’t think I put it that way because I don’t completely understand. But I would totally respect that and there’s no pressure, I was asking for permission.”

You don’t have to completely understand something to recognize when there’s a time to seek permission but you have to be clear with yourself about being able to accept no for an answer. I asked Lex if there was ever a time when a parent told him no.

“One parent misunderstood and thought I was assigning her to read the book to her child.”

It seems to me the great educators need an internal resolve which gives them the strength to get uncomfortable but I imagine sometimes things get scary. I asked Lex if he was afraid.

“I wasn’t afraid of any parent’s reaction. I was prepared to accept their reaction. I was afraid all the time at school. I was afraid of my principal. I was afraid of my colleagues. But I wasn’t afraid of the parents.”

Some books are capable of tying words and emotion together, they reach into a moment and give context to the blur of life. I asked Lex what surprised him in the storytelling.

“In my ignorance, I thought of the history of Black People as being brought here as slaves, which is not ignorant, it’s true, and being held as slaves, as human chattel, but there are many pieces of Black History I still don’t know but I certainly wasn’t aware of the time after slavery where some families were able to own property, to form communities, to have some power.”

History is imperfect, our telling of history is lazy. It pains me when I stop to think about all of the writers left out of my education – deliberately left out – like right now, until this conversation, I’d never heard of Mildred D. Taylor. Why? Who decided all of the writers would be White? Who decided they would almost entirely be men? How do you construct an accurate understanding of the world we inherited without taking into consideration the voices of those who were already here and those we stole from other continents to enslave? History lessons are supposed to be messy and it can be upsetting to bear witness, but I’d rather face the pain than suck my thumb and soothe myself with neutered fantasies.

I feel compelled to let you know there’s a difference between the conversation I taped with Lex and the memory I shared of him telling a joke at my funeral. One is transcribed, word for word. One is stitched together using emotion and memory. I propose both are true. I asked Lex if he felt the way I wrote the telling of his joke at my funeral represents how he remembers it.

“Maybe the only thing missing is I told the set up – not because I thought it was funny – but because I thought it was as heinous as the quote-unquote so-called joke that Chappelle made about Daphne’s death. I didn’t think it was funny.”

I thought it was funny.

I laughed.

It was an involuntary reaction. Maybe it was for the thinking behind the set up and the delivery of the joke, maybe it was a feeling of bearing witness, but in all honesty, I can’t tell you why I laughed because it happened too fast to understand, which is the gift of laughter. This brings me back to a question I’ve been asking myself…

Can you take back the laughs?

Lex taught 5th grade. I was never in his classroom. I did help him schlepp a few boxes when he was packing up his stuff, cleaning out his classroom after teaching for 33 years, but I was never lucky enough to be one of his students. 

I got to thinking, I wondered what it would have been like if Lex were my teacher, all those years ago when I was taunted for the color of my skin, for the coarseness of my hair, for the “snap back action” of my curls, back when the kids in my neighborhood relished flinging the word Nigger in my direction, when the adults in my life were supposed to notice and care and do something about it. 

I know my parents had their own problems, and I’m not diminishing the pressure they must have felt chasing an impossible vision of life on the north shore of Chicago. But I was a child, and I needed help, and I needed someone to notice, someone with the power to stop the constant self-hatred growing inside of me, dangerously.

“The first thing I would do is take you aside and talk to you privately and tell you that by no means is this acceptable. I would tell you this should not be happening to you and in terms of how I’ll be handling it, because I can’t tell you how anybody else is going to handle it, but in terms of how I want to handle it, I never require people to apologize. But what I can do is apologize on their behalf. So first of all, I want to apologize to you for their awful behavior and hurtful words.”

Thank you.

“Second of all, I’d like to know if you need someone to talk to because we have a social worker and it might help to talk to her about the feelings you’re having. So give that some thought and let me know if you want to talk to the social worker.”

I do.

“I would round those kids up and I would let them know it’s not that I don’t love them anymore but I am gravely disappointed in the unkindness. I have said this many times to my students, I say it all year: I can deal with you not understanding math or not doing your homework, but I can’t tolerate meanness. You go home and look at yourself in the mirror and you’re the kid who called him that name? You don’t have to like everybody. If Greg’s not your friend, he’s not your friend, that’s alright. But you can’t talk that way. This is not how we treat each other. It stops. Now!”

I don’t know if you can heal the past with an idea. There’s Fantasy Football, so why can’t there be Fantasy School Day, where you draft a dream team of educators to replay the fumbles of past memories weighing heavily on your subconscious mind. How else do you heal besides crawling around in the uncertainty of memory, stumbling your way through the darkness to face the pain. Maybe we can rewire the DNA of unrelenting abuse, maybe we can turn it into something we can grab ahold of, maybe we can bring it into the present with a promise we won’t pass on the abuse as a phony rite of passage – instead we promise it ends with us, not by pretending it never happened but in reimagining how it could have been handled, how it should have been handled – maybe…

And so on behalf of Dave Chappelle, I apologize to the Trans Community for the awful behavior and hurtful words. The jokes aren’t funny and I’m sorry I laughed. I’m sorry I went along. I should know better, going along for the laugh might be worse than the person who tells the joke because it gives them an audience which builds them up, increasing the reach of their power. 

It’s not that I don’t love you anymore, Dave, and I understand comedy has an element of surprise or the jokes don’t land, but going back to what you did when you reached out to Wayne Brady, there’s something bigger waiting to happen if you stop to remember there’s another person on the other side of the punchline and maybe they don’t feel like being the butt of a joke. 

It doesn’t make them weak, it makes them human.

Speaking of sensitive people, Negrodamus was actually Paul Mooney and Paul Mooney was actually Gay but he spent his entire life closeted and living in fear his desire would be turned against him and punishing the world instead of fixing himself and maybe if he had stopped to get some help, maybe if mental health wasn’t stigmatized, maybe if we accepted our responsibility as a society to acknowledge and dismantle homophobia, to acknowledge and dismantle racist insanity, maybe Paul wouldn’t have felt the need to indict the Blackness of two men he didn’t know, struggling with their own demons, just so he could land a cruel joke.

There are better ways to laugh.

Dave Chappelle found those laughs and tied it all together, turning 2 seasons of sketch comedy into a timeless masterpiece. I suspect he’s still capable of wrapping laughter in kindness but it’s no easy trick, it’s so much easier standing on stage and calling yourself The GOAT than it is being the guy who has the humility to admit he got it wrong and pick up the phone to make a call, to listen, to acknowledge the pain he caused, to see what he can do about making things right.

I’m not a world-renowned seer peddling visions. I’m not a con artist selling access to God. I’m a Fantasy School Student with no idea who this will reach or if it contains the perspective necessary to rehabilitate the playground bully. I hope Dave Chappelle gets help, which is an odd thing to say about someone who’s so famous but I get the feeling you can get trapped by your fame and it’s important to remember there’s no spotlight worthy of hurting someone else.

To quote my Fantasy 5th Grade Teacher, “This is not how we treat each other. It stops. Now!”

3 thoughts on “When Dave Chappelle Schooled Negrodamus”

  1. Perfect timing as I woke up late sitting down to drink my coffeee. Never was much of a Chapelle fan. But I am a Greg fan. ❤️ Next time don’t make me wait so long

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