image (1) (1)Rachel Kaadzi Ghansah and I met recently in her Brooklyn apartment to talk about “If He Hollers Let Him Go.” Her story, which is and isn’t about comedian Dave Chappelle, ran in the October 2013 issue of The Believer and was a finalist for a 2014 National Magazine Award. (Ghansah has also written for The LA Review of Books, VQR and The Paris Review.) We talked about racism, the use of comedy as a weapon and editing as a trust fall, among other subjects.

My comments are in red; Ghansah’s responses are in blue. First, a few questions: 

How did you pitch this to The Believer? How did you envision the story? Was it always meant to be so broad?

Rachel Kaadzi Ghansah: I didn’t pitch it. I don’t really do a lot of pitching because I’m terrible at it and I would rather just write the piece I have in mind.

How long was the reporting and writing process?

The reporting went on for so long because I was just sitting there, bummed out watching Dick Gregory clips. I knew that I needed a scene. I couldn’t just do Neal Brennan and phone conversations. So when I went to Ohio for a couple of weeks, that just added another gap of time in the process. I started the story in late May of that year and by the end of August we were done.

Where does the title come from? I assume it’s a reference to the original, racist version of “Eeny, Meeny, Miny, Moe.” But does it have a resonance beyond that?

I picked the title. I pick all my titles out of superstition. “If He Hollers Let Him Go” is a Chester Himes book about segregation in Los Angeles. I picked it because no one would let Chappelle go, and yet he had been hollering. He was saying, “Leave me the fuck alone,” and no one would. The nursery rhyme never crossed my mind.

Did you ever hear from Dave Chappelle about the piece?


If He Hollers Let Him Go
By Rachel Kaadzi Ghansah
The Believer
October 2013

Although the city of Dayton is small and has been hit hard by the decline of industry, in Xenia and Yellow Springs the land is green, fecund, and alive, even in the relentless heat of summer. Xenia is three miles from where the first private black college, Wilberforce, opened, in 1856, to meet the educational needs of the growing population of freed blacks that crossed the Ohio River. Yellow Springs, a stop on the Underground Railroad, was initially established as a utopian community in 1825. In 1852, Horace Mann founded Antioch College and served as its president. During the ’50s and ’60s, Antioch and Yellow Springs were hamlets of anti-McCarthyism and antiwar and civil rights activism. Today there are a lot of hippies and there’s even more tie-dye. Between the villages, you can drive over rolling hills and pastures and not see another car for miles, and only far off on the horizon will you be able to spot a farmhouse.  I love this opening and I’m shocked you got away with it. I know it’s just a paragraph, but a lot of editors, I think, would push for you to mention Dave Chappelle ASAP. Anyway, why did you begin it this way? I wanted to say, Here’s what surrounds him. If you think about where he’s from as being germane to this story, we should start there. This is kind of like setting up a scene, because at that point I’d spent a week or ten days in Ohio. It was really a fascinating place to me. I was spending a lot of time at the Dayton libraries and I was reading all these histories, so for me it was an opportunity to talk about the things that I had been reading on my own, that were, if not ancillary, at least tertiary to the story of Dave Chappelle–but to me essential. Because I went to Wilberforce and I was fascinated by this school for free blacks that existed close to Dave Chappelle and that his mother worked at for many years. I was just interested in this tiny town giving birth to this really big celebrity.

I spent a week in this part of Ohio, and during my stay I was invited to do all sorts of things with people of all kinds—rich and poor, white and black. I was invited to go flying, dig for worms at midnight, and plant raspberry bushes. My request to drive a tractor was turned down, not because I don’t know how to drive but because the tractor had been put away. In Ohio, there is space for people to do what they want. There is a lot of land, plenty of it. This is where enslaved people ran to, certain that they had finally evaded capture. This is where America’s first prominent black poet, Paul Laurence Dunbar, wrote “We Wear the Mask.” And somewhere in the midst of it all is Dave Chappelle’s home. This is so interesting. It’s just the second paragraph of the story, but what you’ve done here–in telling us all these things you did in Yellow Springs–enriches the entire narrative. I didn’t think it was intuitive.  Well, it was intuitive for me.   Why? Why was it intuitive? That’s the way it went. That’s the way the story began for me. I went to Paul Laurence Dunbar’s house, I asked someone else to ride on a tractor, someone else asked if I wanted to go flying…That’s the way my life is, kind of. Do you know what I mean? Things happen. I went there to do one thing and then all these other things happened, and they were equally interesting to me. And I didn’t think they could happen just anywhere, so it felt very intuitive to say, “Well, this is the sort of place that this area of Ohio is.” In other words, these things are not part of the narrative; they’re part of the location.   Yeah, it’s a location story. It’s about Yellow Springs and the history of Yellow Springs. It’s a historical town. I’m from Philadelphia and I think those sort of places get under your skin. We were in Athens visiting family friends, and they said, “Do you know what it’s like to everyday look up and see ruins?” It’s something that alters your mentality and how you look at time and how you look at the world. And so I felt like Yellow Springs, with all of these Underground Railroad houses and this huge sense of liberation–this free-to-be-yourself-ness–was a part of the story. Everyone there was just doing their thing, and it felt unusual to me. And that’s what I picked up on.

From above, everything seems smaller and less complicated—or at the very least things are put into perspective. From a plane at thirty-five thousand feet it was much easier for me to understand why Dave Chappelle quit his hit TV show, Chappelle’s Show, and said goodbye to all that, and didn’t stop until he got home to Yellow Springs, Ohio. When news of his decision to cease filming the third season of the show first made headlines, there were many spectacular rumors. He had quit the show without any warning. He had unceremoniously ditched its cocreator, his good friend Neal Brennan, leaving him stranded. Chappelle was now addicted to crack. He had lost his mind. The most insane speculation I saw was posted on a friend’s Facebook page at 3 a.m. A website had alleged that a powerful cabal of black leaders—Oprah Winfrey, Bill Cosby, and others—were so offended by Chappelle’s use of the n-word that they had him intimidated and banned. The controversial “Niggar Family” sketch, where viewers were introduced to an Ozzie and Harriet–like 1950s suburban, white, upper-class family named “the Niggars,” was said to have set them off. The weirdest thing was that people actually went for such stories. Chappelle’s brief moment in television had been that incendiary. Why the italics? Emphasis. I think about sentences a lot with rhythm. How would someone write if they were speaking it to you? I don’t like the idea of the written word being in absentia of how we speak–our dialect. With any sentence, it’s how you hit something hard, so people understand, This is where the importance is. Do you read your work aloud? Yeah, always. To other people or yourself? Sometimes I read it to my husband. The problem of reading to someone else is you’re changing it, you’re leaving out words and putting words in. But aren’t you, then, subconsciously making edits that ought to be made? That’s what I try to do when I read it aloud. I’ll sit at the computer just to change it to the way I’m reading it. That’s really important, just so the rhythm is right. I listen to a lot of hip-hop, a lot of rap, and that gets in your ear. And any really great writer that I love has a keen sense of rhythm. Philip Roth and Toni Morrison are my favorite novelists and I reread them constantly even though I don’t write fiction because their sentences are just powerful. I think sentences work better when they have a cadence. Do you have certain writers in mind when you do certain pieces?   No, but I have the pantheon, and they’re always in mind for structural reasons or for sentence reasons or how they make things pop. I’m working on something now and Renata Adler’s “Toward A Radical Middle” is what I keep coming back to. I like how she’s able to keep an even keel and an even tone, while at the same time being very observational and picking up on every detail she’s seeing. It didn’t matter that Chappelle himself had told Oprah on national television that he had quit wholly of his own accord.

Chappelle didn’t seem to understand that these rumors of drugs and insanity, though paternalistic, were just the result of disbelief and curiosity. Like Salinger’s retreat from fame, Chappelle’s departure demanded an explanation: how could any human being have the willpower, the chutzpah, the determination to refuse the amount of money rumored to be Chappelle’s next paycheck: fifty million dollars. Say it with me now. Fifty. Million. Dollars. When the dust settled, and Chappelle had done interviews with Oprah and James Lipton in an attempt to recover his image and tell his story, two things became immediately apparent: Dave Chappelle is without a doubt his generation’s smartest comic, and the hole he left in comedy is so great that even ten years later very few people can accept the reason he later gave for leaving fame and fortune behind: he wanted to find a simpler way of life. You made two bold assertions. Why were they necessary? And was there any worry that you might turn off the reader who doesn’t agree? Well, none of those are assertions really. Name a smarter comedian than Dave Chappelle. And if people don’t miss him, then why are they constantly still looking for him? So, to me, those aren’t assertions–they’re just reads of the landscape. Look, he’s way smarter than Kevin Hart, a close rival with Chris Rock, but doing very different shit. Who else is there? Andy Samberg? If someone disagreed with me, bring it, but bring something, something logical to the argument. And secondly, he states over and over again why he leaves. It gets a little ridiculous. He’s not being oblique about it. So, to me, those aren’t assertions. But why say what you did about Chappelle’s stature? Isn’t it self-evident? You have to build in stakes. If you don’t build stakes into something, well, then the reader has a right to wonder why are you telling me this? Why does this matter? Of what importance is this? It’s a little bit ridiculous to read a story where you don’t know the stakes. To me, it is counterintuitive to what the essay is supposed to do–which is, in some way, to argue for something.

You know you must be doing something right if old people like you.

—Dave Chappelle

Dave Chappelle was in his teens when he first appeared on the comedy-club circuit. He was twenty-three when he and his friend Neal Brennan wrote Half Baked, a now-classic stoner flick about four hapless friends who try to enter the drug-dealing game so they can get bail money for their friend Kenny, who has landed in jail after inadvertently killing a cop’s horse. They were young and had no expectations except to have fun and be funny. They certainly had no idea Chappelle’s Show, another collaboration, would become the most talked-about show on television. But early into the show’s first season, critics at the New York Times would take notice of Chappelle’s “kind of laid-back indignation” and his “refusal to believe that ignoring racial differences will make anyone’s life better.” What Brennan and Chappelle were doing every week was so unusual that the Times declared that “it almost looks like a renaissance for African-American humor on television.”

Chappelle’s comedy found fans in many worlds. At a recent barbecue in Philadelphia, a friend of the host dutifully but disinterestedly interrogated me about my life, and got excited only when my mother let it slip that I was working on a piece about Dave Chappelle. The fourth wall breaks here. It reminds me of something John Jeremiah Sullivan said. He said he liked when the process of reporting a story “gets trapped in the writing of the piece and recorded.” This happens in other areas as well. How and why did you choose to step into the story? That’s interesting, because I don’t feel like I ever step into the story. I always feel like I’m in the story. I would never want to write a story where I’m not in the story. You’re always there. I don’t need to be on the page but I’m present, of course. There are stories where people who have well-defined personalities hold back, but you know they’re so present that they don’t need to be there in first-person. “Sentimental Journeys” comes to mind, where [Joan] Didion doesn’t do what she’d done before in a lot of her reporting, say, “This was told to me” or “This is what the hippies did in Haight-Ashbury. But you know that everything is being filtered through her and you can hear her sensibility. To me, you’re always there. I’m there in how people interact with me; it’s different than if, say, you were reporting or anyone else. What’s happening to me is very personal. It seems necessary, or honest, to say this is how it felt to me as it happened. I don’t like it, generally, when writers insert themselves into their work. It doesn’t often seem necessary and most often gratuitous. I don’t think it’s gratuitous. I think it’s the opposite. In fact, I think the West has this huge importance on saying, “I’m not in the story.” But you’re always in the story. It’s just that you’ve placed yourself in the center, as if it’s not subjective. And part of my subjectivity coming to it, as a woman and a black woman, is that you’re in the story as much as you’re not in the story, even when you’re not present. You can’t remove yourself from the center. There’s a sensibility, especially in journalism, for people to say, “I’m not in the story! It’s objective!” Well, that’s not true at all! You are the filter of the story. You are in it, whether you want to be or not. It’s good to know the vantage point of the writer. That’s why, in “Frank Sinatra Has A Cold,” Talese is in the story. He’s Italian-American. He related to this person in a different way. It’s why Hunter S. Thompson is in the Ali stuff. They’re both from Louisville. It’s awesome when he says we’re both from Louisville, but we probably never encountered each other. Because at the moment we grew up in Louisville, our worlds were splintered. “Aw, man. I miss that guy,” he said. “He was my friend. I really felt like he was my friend.” I hear this a lot, usually from white people, and usually from white people without many black friends—like this seventy-year-old comparative literature professor in Birkenstocks. Part of what made the show so ingenious was that Chappelle’s racial invective found friends in strange places. With a regularly broadcasted television show, Chappelle was finally able to display what writer and activist Kevin Powell described in an Esquire profile as a “unique capacity to stand out and blend in, to cross boundaries and set up roadblocks.” Almost overnight, Chappelle became America’s black friend. He was a polyglot. He told Powell that, growing up, he used to “hang out with the Jewish kids, black kids, and Vietnamese immigrants,” and it was apparent that Chappelle had used these experiences to become America’s consul and translator for all things racial. More than any comic of his generation, he lanced the boil of how race works and also prodded at how nuanced race had become. “Sometimes convention and what’s funny butt heads,” Chappelle confessed to Entertainment Weekly in 2004, “and when [they do], we just err on the side of what’s funny.”

Besides race, three things make Dave Chappelle’s comedy innovative and universal: wit, self-deprecation, and toilet humor. This is the same triumvirate that makes Philip Roth’s writing so original. Woody Allen’s movies, too. Chappelle had a keen sense of the archetypal nature of race, and understood just as acutely how people work on a very basic level. In a Chappelle’s Show sketch about the reality show Trading Spouses, a black man sits on a toilet in a white family’s house and flips through a copy of People magazine while taking a dump. He looks up: “Who the fuck is Renée Zellwedger?” In another sketch, a stodgy, Waspy white man (Chappelle in whiteface) lies in bed with an attractive black woman in classy lingerie. He wants her. But he wants to make love with his pajamas on.

What guided how you wrote about Chappelle’s comedy? It must’ve been tremendously daunting to write about the most famous comedian on the planet without recycling old ideas. How did you reach your conclusions? You sit and you watch thousands of years of Chappelle’s Show. And you’re like, what are the themes that he keeps talking about? What makes this work? It’s just being observational. What’s the common ground that he’s laying out that makes Half Baked work? What’s the common ground that makes Twain’s “Letters From The Earth” work? I think people are bawdy and human and you need some ground-level bawdy, biological stuff to anything that’s highbrow and brilliant. You need to lay the groundwork for your humor. That’s what Chappelle does well and what Woody Allen used to do really well, when he was younger.  

Chappelle did such a good job of truth-telling, on every subject, that nobody knew what to do when he just stopped talking. In no way did his quitting conform to our understanding of the comic’s one obligation: to be funny. To talk to us. To entertain us. To make us laugh. We aren’t used to taking no for an answer, to being rejected, especially not by the people who are supposed to make us smile. Especially not by black men who are supposed to make us smile. I’m generally put off by the use of ‘us’ in stories. Who are you to speak for me? But it works here. Why? Did you have the audience in mind? No, I never think about the audience. That doesn’t come up for me. When I think about “us,” it’s a better way of saying “folks.” It’s the collective. With someone like Dave Chappelle, who really touched millions of people, I think “us” is completely appropriate. There are figures that are that galvanizing and that unionizing and uniting because of the connection they made to so many people, so it is acceptable to say, “This is why we love them.” Michael Jackson would be one of them. It’s a sort of level of celebrity and Chappelle is definitely on it. With him, it’s not hard to find a big group of people who will say, “Yeah, I felt that way about him too.” And yet Chappelle did just that. And so, like everyone, I wondered what had happened. What had happened, and, more so, what had brought Chappelle to—and kept him in—Yellow Springs? At a stand-up appearance in Sacramento in 2004, a frustrated Chappelle lashed out at his hecklers from the stage, yelling, “You people are stupid!” So what was it about this small college town—where hippies slipped me bags of Girl Scout cookies, where Tibetan jewelry stores and fair-trade coffee shops dotted the main street, and where kindly white ladies crossed the street to tell me my wild hair was giving them life How did you respond? The same way I do to lots of weird people who come up to me and tell me they like my hair: “Oooookay.” As long as you don’t touch it or ask me how I wash it, you just keep it moving. —that made it more satisfying than celebrity or fame?

Even before Chappelle himself, politely but firmly, turned down my interview request, I had begun to suspect that the keys to everything he was doing politically and culturally—block parties with Erykah Badu, videos with Mos Def and De La Soul, and campaigning for young black candidates like Kevin Powell, who stressed social responsibility—were interests deeply informed by his parents. What would you have done if Chappelle had talked to you? Would you still have talked to his mother? Do have any idea what sort of piece that would’ve been? That’s so theoretical. So I don’t know. You know, sometimes I don’t like doing interviews, only because people are sometimes not the best observers of themselves. You sometimes don’t get that much information out of them, as opposed to the information you get from people who know them well. His mother is a historian and his father was a dean of community services and a professor of music. Edward Countryman, the American historian, has pointed out some worthwhile context: “Until John Hope Franklin joined the University of Chicago in 1964, no black person held a senior rank in a major history department that encouraged research and trained doctoral students.” But Chappelle, like Kanye West, grew up in a home where black activism and black leftist thought were the languages of the household. No wonder, then, that both Chappelle and West have wrestled so bitterly and publicly with their sense of responsibility to and also their failure to meet those same obligations. Why did you bring Kanye West into the story? Are there other parallels between them? Don’t I explain that? Yes, but aren’t there other people with whom the comparison would have worked? Were those circumstances so unusual?   Um, I don’t know of other people who grew up with Black Panther or radial leftist professor parents who grew up to be very famous in the hip-hop generation. It is rather specific, no? “It’s a dilemma,” Chappelle told Kevin Powell. “It’s something that is unique to us. White people, white artists, are allowed to be individuals. But we always have this greater struggle that we at least have to keep in mind somewhere.” Chappelle’s throwback kind of celebrity and his many concerns about “social responsibility” are faintly reminiscent of the work that his mother, Professor Yvonne Seon, did in the ’60s and ’70s as a scholar of the Negritude movement.

In 1939, the poet Aimé Césaire would return to his island homeland of Martinique, in the Caribbean, after spending years in Europe. The move would prompt his book-length piece of prose poetry, which André Breton would call a masterpiece: Cahier d’un retour au pays natal (Notebook of a Return to the Native Land). Césaire, a gifted writer, was sent to Europe as a young man to study in the center of the French-speaking world. Once there, he reunited with his childhood friend Léon Damas and a young Senegalese poet and future president named Léopold Sédar Senghor. Together, as black men in France, they attempted to educate themselves in a culture where the word negre was inherently a pejorative. To cope while living under the double bind of colonialism and racism, they created “Negritude,” literally a “Blackness” movement.

Sometime after my first few interviews with Seon How did she react to your request for an interview? Was there any hesitation because her son had turned you down? We had many conversations. I never talked to her about her son. I was genuinely only interested in her. I was interested in what that generation of women meant for their children. And there was this whole moment in the seventies and the eighties when black academic thought was really strong. So I was really interested in connecting with Professor Seon to know her experiences. And the thing about her is that her life was absolutely incredible—as incredible as her son’s in a lot of ways. But also, I’m a person who writes about celebrity, but has no real interest in celebrities. Celebrity in itself is interesting, but celebrities aren’t interesting to me. I care more about why people care. And I do care about how people get to the point where other people care about them. So I really like coming-of-age stories and origin stories. That’s what saved this piece. You don’t go blindly to the brightest thing in front of your face, right? The brightest thing would’ve been Chappelle himself. The more interesting thing, I think, was his mother and the foundation she laid for him and his siblings. When you approached her, how did you position the story? I said I grew up around a lot of these guys, and I’m interested in the connection that many of them have professor mothers. And I was interested in their leftism, and their radical academic work–and how the vestiges of it show up in their sons’ entertainment work. So Chappelle was tertiary to your pitch? To me, the story is barely about Dave Chappelle. Ultimately, the story became about a lot of people and things, and one of them was Dave Chappelle. Because if someone is going to tell a story about Gay Talese, they’re gonna have to talk to Nan [his wife], they’re gonna have to talk to his kids. We are each other’s bounties, said Gwendolyn Brooks. We are each other’s harvest. All of these people are always coming into your being. That’s why profiles are always kind of spoked. We start here, but then we follow all of those spokes out to what makes the whole story. To me, she was one of them. Was she eager to talk to you?   She was eager to talk to me. She knows she has an interesting story in her own right. And one that the world needs to hear. She knows that. How can you not? she mailed me an essay that she wrote in 1975 that had been published in a magazine called Black World. The issue features Muhammad Ali on the cover, and in her essay Seon describes Negritude as being more of a sensibility than a literary movement that is fixed in the past. To me, more than anything, it voices the dilemma her son would experience decades later:

When one speaks of Negritude, one may be speaking of either of two quite different things. In its narrow definition, Negritude is a literary movement of the late 1930’s. In this restricted sense, it represents the use by Black French-speaking poets, of the techniques of French Impressionism to break away from French culture and to give creative expression to an inner, African self that had been hidden away. But the broader, more important meaning of Negritude has to do with a process isolated and identified by these poets. It is the process by which Black people, who have been cut off from and made to learn to know themselves again, come to accept themselves, and begin to believe in (i.e. to value) themselves. At what point in the reporting and writing process did you make the connection between Negritude and Chappelle’s own life decisions? That happened before I even wrote the piece. Because I knew that Professor Seon had worked for Lumumba and is a poet herself. So I knew that he already knew about Negritude. Writing about women tends to be about inner lives, domestic lives, household lives. Never lives that go out and change nations. And so, for me, that Dave Chappelle had a mother who knew she could change a nation–as a woman–meant that he was probably imbued with that sense from the moment he was born. Because how many people’s mother can tell them, “I was driving down the road in Kinshasa and they pulled us over with guns…”? It’s crazy! She’s an extraordinary figure.

Seon was born in Washington, DC. Her father was a fair-skinned man who was adopted by a black woman. Although he self-identified as black, by all accounts he looked Greek. He was also blind. On the day Martin Luther King Jr. was shot, Chappelle’s grandfather was on a city bus and overheard rumblings of a beat-down about to happen to a white fellow on his bus. That guy’s gonna be in trouble, he thought. He did not realize that he was the white man being threatened. This anecdote about his grandfather would inspire Chappelle’s “Clayton Bigsby” sketch—the unforgettable short mockumentary about a blind white supremacist who does not know he is black. Where did you get this information? His mother. She told me that story, more than a few times.

Beginning in 1944, Seon’s mother worked as an administrative assistant for the NAACP. Seon tells me about early memories of sitting outside of NAACP meetings and waving hello to the organization’s chief counsel, Thurgood Marshall, who was working on the cases that would dismantle the Jim Crow laws. In the ’50s, when Africa began to hammer off its colonial shackles, her family found itself in the front lines as black American allies.

“My mother was very much one of the people who was paying attention to what was going on in Africa; she knew the ambassadors, we went to the celebrations of independence. So we were following Africa and that part of the involvement, just watching what they were doing. We were aware of the avant-garde, the people who were questing for liberation in Africa.”

Seon was twenty-two when she met Patrice Lumumba, the young, energetic prime minister of the Congo, at a society mixer. That same afternoon, he offered her a job. She went home and asked her parents for permission, and they came back and talked with Lumumba. It was agreed she would fly to the Congo and help Lumumba, who, unlike Ghana’s President Kwame Nkrumah, didn’t have a college degree or much of a background in government. Instead, Lumumba was a beer-selling postmaster who had crushed one of the most dehumanizing, despotic colonial regimes with pure rhetoric and was now learning how to establish a new nation. She made plans to leave in the winter, but on December 1, Patrice Lumumba was arrested. “The hardest part was not knowing,” she says. In the weeks to come they found out: Lumumba had been murdered, most likely by American and Belgian operatives; Lumumba’s pan-Africanism, his vision of a unified Congo, and his utter lack of patience had alarmed the West so much they had had him killed. (Belgium apologized in 2002 for its “moral responsibility” in the murder.) I could ask this anywhere, but what was the editing process like? Light? Heavy? There are editors who want to go in and change everything because…who knows? But Karolina [Waclawiak] was absolutely awesome and she is an author in her own right. Eliza Mills is another incredible editor (she is not at the Believer) who I trust implicitly and I showed her a draft as well. The editing process with Karolina was, I’d send her things and she’d say, “Ehhhh! Do you like that sentence here?” And I’d say, “Actually, I really do.” And then we could have a dialogue. Some people, you end up fighting them. It’s like, “Dude, I would never write that sentence if I was dying. It has no rhythm, it’s flat, it does not sound good.” Sound is really tricky. How do you express to someone that it doesn’t sound good? But it’s as bad as an editor who came to me and said, “This is clichéd.” I thought of something Renata Adler said: If it’s clichéd, point to it and show me the cliché! Because you just saying it’s clichéd is completely subjective, right? Karolina, though, was so incisive, so correct and so encouraging. I was having a meltdown in the process of writing this piece. I was getting married in two weeks, and she was saying, “Where is this piece?” I knew Chappelle wasn’t going to do the interview. So I was like, “I need to go to Ohio.” And they were like, “You need to go to Ohio? For what?” “Well,” I said, “I don’t know but you just have to trust me on this.” And she did. So the editing process was, to me, a tract of trust, a bond. I was constantly asking for things that had seemingly nebulous returns. But every time I asked Karolina to have faith in me, she did. That’s the ideal kind of editor. We were doing trust falls all summer.

But here is the part you should remember if you want to understand Dave Chappelle’s unbridled wit and compulsion to be free: a young Yvonne Seon still decided to take off for the Congo, not knowing what to expect, but knowing that her contact there—a man who was being mourned by Malcolm X and Che Guevara, whose death incited outraged protests all around the world— had been murdered. She needed to fulfill her promise to the dead man and his hope for a “history of dignity” for African people. “We were very much aware that if America was going to have its independence, our independence was tied to the independence of the African countries. And I personally believed at the time that African Americans would not be able to get civil rights until Africa had won its independence, that the two things were interrelated.” Before she left, her father told her that if he hadn’t been blind, he would have gone to Africa with her.

When she returned to the States two years later, Seon attended graduate school and met her husband, William David Chappelle (who died in 1998), in those times of great hope and unrest. In the late ’60s, they came to Yellow Springs to visit friends for the weekend, and, besotted with the town’s counterculture, diversity, and leftist vibe, her husband didn’t want to leave. When Chappelle was two, his parents divorced, and his father returned to Yellow Springs to teach at Antioch while his mother stayed in Washington, DC, with the children. Dave Chappelle has said of his childhood, “We were like the broke Huxtables. There were books around the house; everybody was educated to a college level. We used to have a picture of Malcolm X in Ghana. Last Poets records. We were poor but we were cultured.”

When they reached the age where he and his siblings could start “running the streets,” his mother sent them to Yellow Springs to live with their father. Chappelle returned when he was fourteen. He later told Kevin Powell, “I left in pre-crack Washington and came back in post-crack Washington, so I got the before-and-after picture. It was literally jolting, like, what the fuck happened? My freshman year of high school, over five hundred kids my age were murdered.”  Is this true? It may not be. Even if it’s false, doesn’t that still say something about Chappelle’s beliefs? Why isn’t it true? The highest number of total homicides in a given year was under 500. How much under? I don’t remember. But is there ever an obligation to correct a falsehood that’s in a quote? I don’t think that’s a falsehood. I think if you’re growing up in crack-burdened D.C. in the eighties, saying that 500 kids were killed–even if it’s 300 kids–that’s just being honest to the magnitude of violence that’s you’re living in. There’s an emotional truth. Now, if he said, “I grew up in D.C. and one kid got killed,” that to me is what I’d be worried about–the veracity. Not, though, if it’s emotionally true and speaks to an understanding of the cataclysmic nature of what was happening to that city at the time.

In addition to the typical growing pains that accompany adolescence, Chappelle found himself having to navigate what he described to James Lipton as being “a very segregated city, especially at that time. Statistically speaking to this day—statistically speaking—there’s not one poor white person in Washington.” Not to belabor the point, but is this assertion, which isn’t true, allowed to stand unchallenged because this is an essay?   Ha! I bet he’s right about that. I mean, how many white people were in Washington then? It was called the Chocolate City for something. Let’s look up Washington demographics [takes out phone] I bet there’s maybe one, but there aren’t a hundred. I grew up near Washington, in Reston, where my mother worked for the State Department. So, in 1970, when he was living there, the black population was 70 percent. That’s incredible. You don’t have black cities like that anymore. So it’s 30 percent for other people, and you can imagine that they weren’t just bumming around. They were probably there in government. It’s a pretty segregated city, but also an intensely black city when he was living there.  DC was a far cry from Yellow Springs, and he struggled to adjust to the culture shock. It was his mother who gave him a copy of a magazine with Bill Cosby on the cover. Chappelle felt instantaneously connected to the comic. When he finished reading, he says, “I put it down. And it was like: I’mma be a comedian. And, man, I’m telling you, I could see it so clearly, so clearly, man—this is it. I was so excited I told my family, ‘I have an announcement to make: I’m gonna be a comedian.’”

Because he was fourteen and his mother took him to gigs around the city, other comics called him “the kid.” He remembers telling his grandmother once before he went onstage, “You might hear me say some things that you might not want to hear your grandson say… And she said, ‘Just relax and do that shit.’ I was like, Wow. I had never heard her curse!” How did you decide to credit your secondary sources? There are wonderful quotes from Lipton, Esquire and elsewhere. Was it a difficult trick to properly credit without breaking up the flow of the story? (This is a constant struggle for a lot of writers. Gay Talese, for example, doesn’t like doing it.) I don’t think it’s difficult. If anything, it probably speaks to a generational divide of having the Internet and ease of cutting and pasting. No, I’m just talking about crediting sources. For instance, in “Frank Sinatra Has A Cold,” Talese took a scene from a story written by Maurice Zolotow, but he didn’t credit him. “I just clipped it,” he said. He didn’t mention Zolotow because he didn’t want to. So it’s not about finding the information. That is probably also generational. How can you get away with not crediting someone’s information that anyone else can find? People get in trouble for that all the time. It wasn’t an uncommon practice among the New Journalism guys. Tom Wolfe did it, too. There’s no latent privilege going on with that crowd, right? I sort of can’t imagine taking someone’s hard work and not putting their name in it. Because I wouldn’t want someone to do that to me because people have done that to people who look like me. I love the blues but how those guys were robbed breaks my heart. People deserve credit for what they do.

Over lunch in Ohio, Seon tells me, with the same optimism as every other time we’ve talked, about the years she spent in Kinshasa. Her stories are populated with dangers she still seems impervious to: Évariste Kimba, a prime minister who soon succeeded Lumumba, was also executed, and the Congo was at the start of a long period of war. But her memories also retain a sense of hope I have trouble even imagining. “You know,” she says, “I’ve never gone back to the Congo, because it is difficult, you know, to look back at a place that was so full of possibilities and see what has happened. That is always hard to see, isn’t it?”

There is a strange moment in James Lipton’s interview with Chappelle where the comedian discusses his decision not to attend college. “I was the first person in my family not to go to college, that had not been a slave.” The audience laughs. I can never tell if they realize that he is serious. Can we talk about the structure? It’s not a classic profile structure. In the two grafs above, for example, we have two seemingly disjointed moments—Seon in Kinshasa and then the Lipton interview. And that’s directly followed by a leap to Muhammad Ali. Clearly, there’s purpose here. The jumpiness is how you get all these things to fit in. You need sections, which help you think about the piece as small parcels. If there are drastic jumps, think about how you end your graf and how you begin the next graf or section. How did you make sense of all the information? Do you use an outline? No. But I write down the theme from one section to the next. And sometimes I’ll write the grafs and then cut them out, physically, and move them around, so that it becomes something palpable and I can think about the flow. You can take up the whole living room, but you need a very supportive roommate or significant other.

In his fantastic profile of Muhammad Ali, Hunter S. Thompson writes that “the Champ, after all, had once hurled his Olympic gold medal into the Ohio River, in a fit of pique at some alleged racial insult in Louisville.” The medal was a symbol of a white world that Ali “was already learning to treat with a very calculated measure of public disrespect.” Like most people of the post–civil rights generation, I think that Chappelle, whose family had long been free, educated, leftist, and radical, had hoped that his success would not need to follow that same militant path. Despite the fact that four in ten white Americans do not have any black friends As I read this, a study has come out that 75% of white people do not have a single black friend. So apparently the problem has gotten even worse. I don’t think it’s unusual. These days I don’t really care if you don’t have a black friend. I care if you don’t have a black boss or a black employee or a black coworker. Friends, to me, are neither here nor there. But what that statistic meant for me is that we aren’t even comfortable around people unfamiliar from each other. So the viewpoints are going to be disparate. But what Chappelle did is he became this great interlocutor and he was able to do a lot of that going in-between. When you grow up in a diverse environment, you’re able to have a conversation with anyone. and more pressingly, that all too many workplaces are integrated only in theory, I think Chappelle hoped that he could bring Yellow Springs’ open-mindedness to the world. For a while he did, but then he became aware that his brand of humor was not without a history and was forced to acknowledge its context. Next came conferences with suits at Comedy Central about his use of the n-word and his being chastised in the press, and finally he was humiliated and called insane. Like Thompson once wrote of Ali, Chappelle was put through “one of the meanest and most shameful ordeals any prominent American has ever endured.” Without knowing his history, Dave Chappelle’s decision to figuratively toss his gold medal into the Ohio River does seem like a bizarre, illogical act that abbreviated a successful career on its ascent. But was it illogical? Hardly. Revolutionary? Possibly. To turn his back on Hollywood, to walk away from the spotlight because it was turning him into a man he didn’t want to be—a man without dignity—was a move that was, in a way, Chappelle’s birthright, his own unwieldy kind of Negritude.

There’s no friends like the old friends.

― James Joyce

Why did you use quotes like this throughout? How were they chosen? Reminds me of “Frank Sinatra.” Talese used quotes? Wow, he is so great. [Hunter] Thompson uses quotes, too. And I like it. The quotes let me get where I need to go. They serve as epigraphs. They help to get me started, not just transitionally but mentally. So I could say, “This is about this.” They’re focal points or writing prompts. Was that always the plan? Yeah, these were all in the first draft.

“I wasn’t crazy but it is incredibly stressful,” Dave Chappelle explained to Oprah on The Oprah Winfrey Show in 2006. With his mother sitting in the front row, he was trying to explain why ten months years earlier—without explanation to his wife, to Brennan, or to his bosses at Comedy Central—he had quit his show.

“I would go to work on the show and I felt awful every day,” he said. “I felt like some kind of prostitute or something. If I feel so bad, why keep on showing up to this place? I’m going to Africa.” Five years have passed since that interview, and Brennan has gone on to write for President Obama at the White House Correspondents’ Dinner and to work with comedians like Amy Schumer and Chris Rock. Brennan repeats to me how much he respects Dave, but he tells me that being “trashed” by Chappelle on Oprah still bothers him. In 2011, he told a reporter: “You know, for a black artist that’s beloved to go on TV and say he was victimized by a white corporate structure, that is like white-people nectar, it’s like white liberal nectar, like, ‘Oh my god, this young black man has been victimized.’ Dave did real well from the show, you know. There was a huge benefit to Dave. So the idea that somehow he was victimized . . . My experience was he wasn’t victimized and that it was a matter of pressure and needing to eject from the pressure.”

Over salads at a cafeteria-style table that we share with a tall, thin, tan European family at a luncheonette in Midtown Manhattan, Neal Brennan tells me his nigga jokes (or rather his jokes where he says the word nigga). Two weeks earlier, in New Orleans, I had hung out in the whitewashed wings of the Civic Theatre and watched Brennan direct his first Comedy Central one-hour special. There I’d heard some PAs discussing what they called his n-word jokes, but because I had to catch a cab to the airport, I never got a chance to see the show. In New York, sitting a few feet from each other, I tried to prepare myself for the inevitable, but each time I thought about it my hands had instinctively cocked and curled into fists under the table. At this point, there isn’t even a suggestion that Brennan is white. Why? I wonder if it’s because I thought that Neal Brennan is kind of a celebrity? Also, I can’t imagine a black person saying, as Brennan does, “Oh my god, this young black man has been victimized.”

Brennan says Chappelle’s Show told two stories: “What it was like to be a dude, and what it was like to be a black dude.” He grew up in the Philadelphia suburbs and is a former altar boy, the youngest of ten kids in a large Irish Catholic family. He is very thin and he has what he himself calls a “roguish charm.” Brennan is really, really funny and quick. He wears a uniform of jeans, sneakers, and a T-shirt. He has large ears and wide eyes and spiky hair that is often gelled to a point, cockatoo-style. As we talk, I realize that I recognize many of his expressions from the show. Brennan tells me that as a writer he knows how to shape and structure a joke. He directs the jab. “My job and life are basically just saying, ‘Hey, say this.’ Say, ‘Doctor says I needs a backiotomy.’”

Brennan met Chappelle when they were both eighteen. Everyone else in the New York comedy scene was in their late twenties. “Comedy,” he shrugs and sighs deeply, “is incredibly racially integrated. Probably the most diverse workplace there is, and it’s not clannish—there is a table at the Comedy Cellar where we all go, and you can look around some nights and it is Mexican, white, Jewish, black. You are friends based on your comedy ability, not based on your age or something. Like race is almost irrelevant.” Brennan studied film at NYU during the day, and at night he stood outside and worked as the annoying guy who yells, “Hey! Come inside and check out the comedy show!” Chappelle had moved to New York to do stand-up and was working in Washington Square Park, learning from a street comic named Charlie Barnett.

Neal and Dave had similar sensibilities: they liked the same movies (Spike Lee Joints), the same music (hip-hop), the same TV shows (Family Ties). It was kismet. “Chappelle had been on all of these pilots and had been paired with all of the wrong writers, wrong actors; like no thought to chemistry. Just: ‘He’s a hot writer and you’re a hot stand-up,’” Brennan says. Entertainment Weekly would say of Chappelle’s first sitcom: “The worst thing about Buddies is that it makes racism boring.”

Years passed, and Brennan left New York to live in Los Angeles and write comedy for Nickelodeon, but he stayed in touch with Chappelle. Their film, Half Baked, was totally unexpected and came about quickly. In fact, they had only a month to outline it. “We pitched it. Universal sold it in, like, March, and we were shooting it in July. Which is crazy. Really crazy. But we didn’t know anything because we were, like, twenty-three.” Is all this biographical information up until now, and following this, all from Brennan? Or was a lot of this already in the public record? All from Brennan. We talked a lot. We hung out briefly in New Orleans, I went to his show, we talked on the phone.

From the moment they arrived on the set, Brennan says he knew that something was off about the production. “First of all, it should have looked more like Kids and Trainspotting. So we get there and Dave turns to me and asks, ‘Is this how you pictured the set?’ And I go, ‘Nope.’ And he goes, ‘Me neither.’” Neal shrugs again. “But again, twenty-three. And there is just nothing you can do. I’m not a fan of the movie. Dave’s not a fan of the movie.” Directed by Tamra Davis, Half Baked was released in 1998, the same weekend as Titanic, and flopped. Brennan and Chappelle stopped talking for a while. These silences are themes in their friendship. I ask him why. “I guess not wanting to acknowledge responsibility, negative association, you want to leave the scene of the crime. Like having a child die and the parents want to get a divorce.”

It would be the first defeat in a series of many. After Half Baked, Dave bought his “Fuck you, Hollywood” farm, sixty-five acres of land in Ohio. He was living there and having a tough time professionally. Killin’ Them Softly, his one-hour special, came out in 1999. Brennan is blunt about it: “No one cared. But Killin’ Them Softy is a great one-hour special.

“Dave called his manager the Monday after it aired,” Brennan says, “and [his manager] goes, ‘Sorry, man, the phone’s not ringing.’” That is how it was. It cemented a sense within Brennan and Chappelle that show business is built upon what’s hot and what’s not, and, worse, that show business is random, anti-intellectual, and often pretty far behind. “We were the underdogs. We were left for dead and came from behind and did CPR on ourselves.” He pauses and peers over the heads of the towheaded European family sitting next to us. “To give you a sense of things, this is how little respect Dave was getting: we pitched Chappelle’s Show to one station and they literally looked at us like we were lepers. Like, because Chris Rock had just gone off the air, they were like, ‘Chris Rock is everything and you’re nothing, Dave.’ Then we walk up Fifth Avenue and pitch it to Comedy Central. They buy it. And it becomes the show. And now Chappelle’s Show has sold three million copies on DVD.” (It remains the world’s top-selling TV-to-DVD series.)

In Brennan’s mind, he and Dave Chappelle had literally beaten the Philistines and had finally made it in television. But, as Chappelle told Oprah, this was not at all true. When Brennan discusses the demise of the show, he discusses it as a conflict about renegotiating the terms of the third season. Or, as he told fellow comedian Joe Rogan How many secondary sources did you use? I have no idea! I don’t even think about it. It just happens. But I think I mention every single secondary source I actually used. Maybe 30 or 40? in an interview where Brennan looks visibly pained, “It became an ego thing, once the negotiations started. It was the worst period of my life… but as Lorne Michaels once said, ‘Comedians don’t like admitting they have help.’” Brennan says that at the height of the contretemps, they both said awful things to each other. When Chappelle discusses his exit, he does not deny that things went haywire, but he attributes it mostly to his discomfort with the material, the politics of the show, and the climate on the set. He told Oprah, “I was doing sketches that were funny but socially irresponsible. It was encouraged. I felt I was deliberately being encouraged and I was overwhelmed.”

I ask an older friend who is black and a theorist of sorts what he thinks about Chappelle’s Show. I get an answer that surprises me with its vitriol: “Chappelle was at the end of the one-hundred-and-fifty-year minstrel cycle and fifty years after the height of the civil rights movement and ten years after the beginning of Southern hip-hop and in the midst of the most coonish aspects of dirty South hip-hop. He wrung the last bits of potential energy out of taboos that had been in guarded reserve that show niggas as violent, unintelligent, unlettered beasts. And he portrayed niggas that way (while maintaining an ironic distance from those caricatures). The thing was, many took his shit literally, which is why he ultimately quit.” This is such a wonderful quote. Why did your friend want anonymity? I’m going to let the cat out of the bag with that one. That’s Richard Nichols. He was probably the most brilliant person to come out of American culture in the 20th and 21st centuries. He was the manager of a hip-hop group. He passed away in July. He was more of a father figure to me than anyone I knew. He was kind of a theorist, of sorts. When I say that he said it with vitriol, that vitriol wasn’t directed at Chappelle. He loved Chappelle. It was directed at me. It was the nature of our conversations–probing, open-ended and theoretical. He was an absolute genius. And when you talk to people like that, they get exasperated. Like, “What do you mean? Obviously it’s this!” It was just a result of me asking, “What is it?” And that’s what it was. Him yelling at me. So, why didn’t you mention his name? At the time, he had to protect his position as a manager, someone negotiating business on his own. Maybe I should be respectful of that, but he’s too brilliant for me not to go on the record. Now that he’s not here, I’m going to. Was the quote spoken or in an email? It was probably a Gchat. That was our primary means of communication towards the end. I go back and watch “The Mad Real World” sketch, a spoof of the MTV reality show. In the sketch a white man moves into a house full of black roommates and, in the ensuing weeks, his father is stabbed while visiting, his blond girlfriend is turned out by two guys, and the living room is regularly transformed into a makeshift nightclub. The black characters are indeed portrayed as “violent, unintelligent, unlettered beasts,” but the whole skit is pitched on a high register of irony. When I ask Brennan how he dealt with backlash about the show’s use of the n-word and its edgy racial humor, he objects. “As much as people say that about Chappelle’s Show, no one ever got pissed. People ask, ‘Were you worried?’ and it’s like, no, because it was all founded on real, empirical observations and lived lives. Like, that ‘Real World’ sketch was a discussion we had been having for a decade about black people on The Real World. The guy who pulled the blanket off the girl was Dave’s best friend. So we knew what that shit was like.

“Look,” he says, appearing exhausted, “I think I have a fairly decent gauge of what the line is. It is not perfect, but, like, I say the n-word eight times in my stand-up. And it works. People can tell if you mean it. And the other thing is I never say it, I’m always paraphrasing someone. And… I open up by shitting on white people. And pedigree. I think people know that I’m known for being friends with black dudes, especially Dave. And I talk about that, I talk about being called it. I talk about the first time I was called the n-word. I get called the n-word every day. I can show you texts.”

Scrolling through his phone without looking up, he tells me, “So it is a weird thing where you expect me to inhale something and not exhale. And people are like, ‘You can’t say that.’ But I get called it every day. Constantly, for twenty years.” I choked on this a bit. I kind of want to shake Brennan and yell, “THAT IS NOT THE SAME THING, WHITE PERSON.” How did you react to this? Generally, I try to keep very cool with stuff like that before I flip out. But usually it takes about ten attempts. I don’t like people saying n-word at all, ever. And I was expecting him to keep pushing it and then I would just explode. We, as people of color, become very socialized with accepting people’s bad behavior. And so I wanted to indict our acceptance of that behavior, as much as I wanted to indict the people who test us with that behavior. But I did what was comfortable in the moment, which was to laugh. Which was to say, “He’s guilty of something here and I’m guilty of something here.” Which is why Chappelle is even more interesting. He finally said, “Fuck this bullshit. I’m fucking out. You can call me crazy, but I don’t give a fuck because my dignity’s intact.”

Later on, Brennan brings up an idea first posited by the psychologist Beverly Tatum about the ways we tend to segregate ourselves as we get older and grow apart from our friends of different races. Neal tells me, “It’s like when black kids sit at the lunch table with only black kids, and the white kids sit with white kids. I think it is just like, ‘Well, they look like family.’ It is just some animal shit. It is safety.” When I read Tatum’s book, she says something that sticks with me: that so often the difficulty in discussing race is about working around the divide of that which we do not know. As I listen to Brennan talk, I think about how he is right, that comedy is different. Comedians live for the joke and the joke alone. White writers have long written jokes for black comics with great success (my favorites being Ed. Weinberger for Bill Cosby and Louis C.K. for Chris Rock), but at the same time none of this goodwill can negate the possibility that Chappelle experienced what his mother had written about twenty years before: the desire to “learn to know himself again.” And that for all the post–civil rights progress we have made, it is possible that you could be best friends with someone of a different race without being able to enter worlds and spaces that they can, or in the way that they do. I think this is absolutely true. Is it specific to race? Is this also true of men who are friends with women? It’s with many things. But race is one of those things that people always want to immerse themselves in. You see young white people constantly saying, “I’m a black, or I’m so down,” and they don’t want to take on anything. Anything but the burden, for them. Like Iggy Azalea, who is dreadful, people don’t want to do it for more than fun. Ultimately, being anything is not always fun. It’s life. I think there are people, actually, who give up their race and identities, but I’m not entirely sure that they give up their privileges. Who? James McBride’s mom. A Jewish woman who effectively gave up her life as a Jewish woman to live in this black community. She had black kids at a time when people didn’t do that. What I find interesting is you don’t see a lot of people of color who are able to do that, who are able to give up their lives and say, “Hey, guys! I’m white today!” It’s a one-way street. It’s a privilege. So maybe you’re not so much giving up your privilege as exerting it.

After two hours of remarkably easy conversation, I can tell it is time for the moment I’ve been clenching my fist about. Maybe he had needed to feel me out. Neal Brennan, who definitely embodies the best of the easy wit of Chappelle’s Show, goes for it. This moment is the point of highest tension in the story. To be blunt: a black woman confronts a white man about race. And the story itself is about a black man confronting how the world at large (both white and black) perceives his comedy about race. Did you see yourself as a stand-in for Chappelle here? Maybe I did. I remember thinking that Brennan didn’t really know what he was talking about at times, and he knew so little about Chappelle’s mom. That seemed like something he would know and also think about, when he’s popping off saying the n-word constantly to this dude. I mean, how long is that gonna fly for? Ta-Nehisi Coates wrote about him after this piece and I realized then that people tend to see that Neal Brennan is someone who has both a good and bad gauge of things.

“The joke in my act is: ‘It is so bad I call myself it when no one’s around.’ It will be lunchtime and I’m like, Nigga, you need to eat. And I’m like, Who are you talking to?”

My hand unclenches. His n-word joke reminded me of the weird moments when I’ve been around young white men who identify with hip-hop culture and who, for some strange reason, despite their stated best intentions, need to access that word as proof that they are accepted or acknowledged by the community they are involved with. They do not realize the hubris and dominance inherent in the act of wanting to use that word. Brennan’s joke is a joke on those guys, but it is also, inadvertently, a joke on himself. I think he knows this. Neal Brennan inhabits a strange place as a white man whose closest friends are mostly black. But what, if anything, does that mean? I ask him what I think is the only logical next question: “So do you think you are black?”

“No!” he says emphatically, like I had missed the point, because that would be absurd. “I also think that is a silly thing. Like I’ve never spoken Ebonics.”

“Do you think that you’re a racist?” I ask, but not because I think Brennan is any more racist than any other white person, especially if racism is viewed as a system of white privilege and unearned benefits. I ask this because part of knowing where the line is is knowing where you situate yourself along it or against it. I love that you asked this. I think his answer is a cop-out. Yeah, it’s a pat answer. But what does anyone do when asked, “Hey, are you a racist?” I was really asking Brennan how self-aware he was.

“Uh, I think that everybody is racist. It is a natural human condition. It’s tribal.”

Another evening, Brennan and I talk about what the ride of success felt like. He remembers hanging out at a club in Arizona where he and Chappelle were approached by a white fan who was loose with his use of the word nigger and who praised Chappelle for making it so funny. “It was awful,” Brennan recalls.

The thing is, I like Neal Brennan. And I got the joke, I think. But when he first told it to me, there was an awkward silence that I think both Brennan and I noticed. The cafeteria seemed to swell with noise. And for a brief moment, my head clouded, and there was nothing I could think of to say, so to get out of the silence, I did what was expected: I laughed. When I got home, this troubled me deeply. On the whole, how did working on this story affect you? I was just going crazy in general because there was a lot going on. But I remember being deeply engrossed in comedy, more tragic comedy. Comedy was the id to me. We all have that accurate, let-it-bleed reality in us that we keep tucked away because we’re not brave enough to let it out. It was definitely something I became more aware of.

You can’t say anything real when it comes to race. That’s why Bill Cosby’s in such trouble for saying black folks have got to take responsibility for their own lives. I spoke at my high school last week and I told them, ‘You’ve got to focus. Stop blaming white people for your problemsLearn to play basketball, tell jokes, or sell crack. That’s the only way I’ve seen people get out.’

—Dave Chappelle

Last time I was down South I walked into this restaurant, and this white waitress came up to me and said: “We don’t serve colored people here.” I said: “That’s all right, I don’t eat colored people. Bring me a whole fried chicken.”

—Dick Gregory, Nigger

 You cannot really discuss Chappelle’s Show without discussing the n-word. Why ‘n-word’ and not ‘nigger’? As noted below, this puts you at odds with Dick Gregory. I just don’t use it. I don’t like it when white people use it, either. Like you. I think this is the first time I’ve said it aloud. I just don’t think it’s a word to use. I use it socially with other black people, but I think there are private conversations, right? The stupidest argument I’ve ever heard is, “You say it, why can’t I?” All cultures have things that one says that we can’t say to other people. If you don’t know that, then you haven’t existed within any sort of subculture or culture. I asked because you can use the word. But I wouldn’t use the word with you. I wouldn’t use the word with the general public. I don’t use the word with the white people in my life. It’s a private conversation. One also cannot discuss the n-word without discussing Dick Gregory. Neal Brennan and Dave Chappelle weren’t even born yet when Dick Gregory bounded onto the American comedy scene and asked to stand flat-footed or to sit down and be spoken to like a man. Yvonne Seon tells me that when Dick Gregory campaigned for president in 1968, “we all had our eyes on him.” Dick Gregory is a larger-than-life sort of man. To reach him, you have to get past his wife of fifty years, Miss Lillian. “You were lucky,” Gregory tells me. “She is tough. She once told the president I’d have to call him back.”

Although things have slowed down from the days when he commanded a weekly rate of something just shy of fifteen thousand bucks, when the only peers in his earning bracket were Woody Allen, Mort Sahl, and Lenny Bruce, Dick Gregory is still on the move. All of his activity is made even more remarkable by the fact that he is now eighty. He still runs and does regular juice fasts, and his long white beard makes him look like a Methuselah among men. And maybe he is. Richard Pryor once said: “Dick was the greatest, and he was the first. Somebody had to break down that door. He was the one.”

Before Dick Gregory, there were no elegant black men in comedy. The generation before Dick Gregory’s grew up on Stepin Fetchit, the stage name of a black actor named Lincoln Perry and one of America’s most famous black personalities for more than twenty years. These days it is difficult to find clips of Stepin Fetchit and the existing films are rarely shown. Stepin Fetchit acts like a shuffling, befuddled fool, and because of this many of Perry’s films have been deemed offensive. Little remains to show his enormous influence on- and off-camera: he was the first black A-list actor, a millionaire during the Great Depression; he owned a fleet of limos and sports cars and he employed a retinue of Asian maids and butlers. He carried guns, he wrote essays for black newspapers, he was handsome, he was a Hollywood outlaw—but none of that mattered on-screen. I can’t imagine how much research you did for this piece. How long was the original draft? We didn’t cut much. Maybe two pages. What kind of stuff did you lose? Stuff that was kind of dangling, repetition. On-screen he stooped his neck, and dropped his bottom lip, and acted as shiftless and stupid as possible. Stepin Fetchit is the id figure, in characterization only, that sits on Chappelle’s shoulder in one of his skits and demands that Chappelle make himself happy and order chicken during a flight. It is not the chicken that is the problem, it is the familiarity of the characterization. That whether Chappelle liked it or not, whether Dick Gregory liked it or not, this was the precedent.

“When the Playboy Club brought me in,” Dick Gregory recalls, “up until then you could sing, you could dance, but you could not stand flat-footed and talk and just tell jokes, because the people upstairs didn’t want folks to know just how intelligent black folks were. [The Playboy Club] brought me in, though, and it opened up the floodgates. Now,” he says, “Will Smith’s movies alone have made three billion dollars.” Dick Gregory’s gig at the Playboy Club started in 1961, and three years later he would write his memoir, entitled Nigger. This is the part of his dedication to his mother that is often quoted:

“Dear Momma—Wherever you are, if you ever hear the word ‘nigger’ again, remember they are advertising my book.”

When I suggest to Gregory that he used his comedy as a weapon, he shouts, “What?” so loud I get scared. “How could comedy be a weapon? Comedy has got to be funny. Comedy can’t be no damn weapon. Comedy is just disappointment within a friendly relation.” This surprised me. I can’t tell if Gregory is being modest, if he didn’t understand what you meant, or if he genuinely believed this. Why, do you think, doesn’t he see comedy as a weapon? It is, right? Well, it’s the sense that comedy isn’t more than the sum of its parts. If it’s not funny, it can’t be a weapon. So what he means is, the forefront of the joke is not to be a weapon; it has to be a joke. It either makes you laugh or it doesn’t. Can’t it be funny and a weapon? Your joke could be a weapon, but it wouldn’t necessarily be a joke. Jokes and weapons have two different functions. That’s what he’s saying. Is his understanding generational? No, I think that’s a comedian’s understanding. Chappelle, he says, was very good at it. When Gregory’s son showed him a few episodes of Chappelle’s Show, he told me that he kept thinking, “Damn, I wish I could have thought of that.” Then Gregory volunteers to tell me the names of the three greatest comedians of all time, and in a proud and awesomely fraternal way, he says, in order: “Lenny Bruce, Richard Pryor, and Mark Twain.”

“Yes,” I say. “But isn’t it difficult to be that profane and that profound, in droves, especially as Twain in Pudd’nhead Wilson?”

“Did you say Pudd’nhead Wilson?” Gregory shouts.

“Yes,” I say, scared again that I’ve said the wrong thing.

Pudd’nhead Wilson! Brilliant stuff! I could kiss you! Mmhm,” he says. “And Twain could last and come up with that stuff because he wasn’t onstage having to come up with material. But listen,” he says, waiting a beat. “Nobody said comedy was easy.”

Dick Gregory admires Mark Twain’s audacity as a white man to discuss race in America. He hates the idea of concealing the word nigger behind euphemisms like the n-word, and he seems to think it should be a shared burden. “Before Twain, no white people would ever write about lynchings. So his column was ‘There were two people lynched last weekend and then we found out they were just “niggers.”’ And then he did the whole article about how the good Christian church people were there. And the white women brought their babies and children were selling Kool-Aid and lemonade, like, ‘So what? They were just niggers!’ That was the first time that anyone in history wrote anything like that, nothing about those gatherings had ever been written about lynching! That had never been done before! And like that, that is comedy!” When I ask Estee Adoram, the lovely, legendary, no-nonsense booker at New York’s best comedy club, the Comedy Cellar, what sort of person becomes a stand-up comic, the first thing she says is “A very brave person. A person willing to be laughed at.”

When I read about Twain saying the word nigger, in the exact same way Neal Brennan did, it does not raise the hairs on my neck. I do not think we want censored comics. It occurs to me that this piece is as much about your own self-education as it is about Dave Chappelle. Am I overthinking it? No, you’re right. Because, while I liked comedy, I didn’t know much about it. I had to figure out how it worked. I tried to get as close to the answer as I could, and the learning process is what you’re hearing. But I’m given pause. Estee tells me she can sense when there is “an unfunny bitterness behind the joke.” The fun of humor is the way it pushes at the boundaries. The joke is indeed a tricky thing. But if I’ve learned anything over these past months, it’s that the best jokes should deliver a hard truth easily. It is the difference between asking girls in the crowd how their butt-holes look—a roast my sister and I endured one night at a comedy club—and mastering the subtlety of the uniquely American art form of stand-up comedy. Dick Gregory has a joke for me:

So I’m standing at the airport and I see this white lady talking to her daughter. Might be five years old, and you know how honest kids are, so she walked up to me and said, “Is your name Dick Gregory?” And I said, “Yes.” And she said, “My mamma says you have a tail.” And I said, “Yes, and you tell her my tail is in my front.” What’s it like interviewing Gregory? Is interviewing a legend difficult? How do you maintain your composure? Well, I grew up around show business. Celebrity doesn’t really intimidate me. Socializing with anyone might be difficult for me, but interviewing is just game face.

Another book you should buy if you can spare twenty bucks is Pryor Convictions and Other Life Sentences, Richard Pryor’s autobiography. In it, he tells of a dinner party thrown in his honor by Bobby Darin. Pryor is seated across from Groucho Marx, who told him “that he’d seen me on The Merv Griffin Show a few weeks earlier, when I’d guested with Jerry Lewis.”

It hadn’t been one of my better moments—Jerry and I had gotten laughs by spitting on each other, and Groucho, it turned out, had a few things to say about that.

“Young man, you’re a comic?” he asked.

“Yes,” I nodded. “Yes, I am.”

“So how do you want to end up? Have you thought about that? Do you want a career you’re proud of? Or do you want to end up a spitting wad like Jerry Lewis?”

The man was right… I could feel the stirrings of an identity crisis. It was coming on like the beginning of an acid trip. Groucho’s comments spoke to me. “Wake up, Richard. Yes, you are an ignorant jerk, pimping your talent like a cheap whore. But you don’t have to stay that way. You have a brain. Use it.”

The next sentence? “The thing was, I didn’t have to.”

The thing about Chappelle is that he wanted to use it, and he knew how. There is no doubt that Chappelle’s Show is his finest work, but the block party that he put on and filmed in Bed-Stuy in 2004 is also a revealing production in the sense that we get to see the comedian almost at rest, listening to the music he enjoys with his celebrity friends. I was there, both in the crowd and backstage, and there was a remarkable amount of solidarity, love, and exuberance even in the drizzly September rain. This is, I think, the first time you talk directly about your own connection to Chappelle’s work. And that’s an interesting thing about this story, that your connection is deep, but also long. When did you start thinking about writing it? Oh, man. I’d been wanting to write about Chappelle for so many years. I’ve got everyone I want to write about in my mind. Anyone I’ve ever written about has been on my mind since I’ve known about them. That’s why I don’t like it when people ask me if I want to write about someone. My sister and I, growing up, were really nerdy girls. We had like three VHSs. One was Wayne’s World and we had it memorized. Every single line. She was Garth and I was Wayne, only out of age difference. And after we outgrew that, somehow she acquired Half Baked. My sister is five years younger. She’s in almost every piece I write. She’s the Robin figure in my Batman caper shit. So she got Half Baked and I thought, “What twelve year old kid gets Half Baked and knows all the lines?” She knew the lines before she’d even grown up, which was bizarre but really funny. And Pootie Tang, too. She had the VHS of that, too. But Chappelle we deeply connected to as black nerds. It was like, Oh snap, here is this guy that perfectly summarizes our life in an academic world, growing up in a diverse, hippie community, moving around a lot, being a black weirdo in a family that had more books than kind of money–exactly like us. That was Dave Chappelle’s life, too. When he came out with Half Baked, we both thought, “He is us!” So, he’s always been in my mind, kind of like a totem. There’s a real connection here between the writer and the subject. Oh, yeah. I saw Mike Myers on the street the other day while we were driving. He was all alone. I saw him and I said, “Mike Myers! Yaaaaaaaayyyyyyyy! Party on, Wayne!” He did the hand wave back and I almost lost my mind. There are people who you hope will see you because you’ve seen them for so long. Half Baked and Wayne’s World were the two most important childhood movies of my life. Deep connections to those guys. The kind that I can’t forget. Watching a triumphant Lauryn Hill resplendent in cream slacks and a Yankees cap, reunited with her bandmates from the Fugees. Looking down from a nearby roof, I believed anything was possible—for them, for us Who is “us”? Well, here ”us” is black people. Chappelle was the kind of celebrity who wanted to reach out to fans who looked like him, and it was clear that as much as he aspired to universality, he realized that “the bottom line was, white people own everything, and where can a black person go and be himself or say something that’s familiar to him and not have to explain or apologize?” So sometimes it was very nice to have, as the comic himself said, “Five thousand black people chillin’ in the rain,” like a Pan-African Congress right off of Putnam Avenue.

When I ask Yvonne Seon what she thinks about the n-word and how easily it is used these days in hip-hop culture, she says, “There has always been a tendency to try and rehab a word that has been used as an epithet for you. It’s a way of claiming something that hurt you, hoping that you can say, ‘Now this word won’t hurt me anymore.’ It’s a part of the attempted healing. When James Brown sang, ‘I’m black and I’m proud,’ that is an example of how he tried to rehabilitate that word. Because there was a time when I was growing up when you didn’t call anybody black unless you wanted to get knocked into next week. There was too much shame involved.”

“Do you think—” I start.

And she laughs and cuts me off with a question. “Do I think, like, ‘I’m black and I’m proud,’ ‘I’m a nigga and I am proud!’ could exist?” We both laugh at the absurdity, and also the very real possibility, of that song. “Hm,” she says. “I have trouble with the word nigga. I associate that word with lynching, violence, and hate, and I don’t associate the word black with that. But I do associate the word nigga with that history. So it’s not a term that I could ever use easily or encourage the use of. There have been articles written about teaching this history, and we’ve discussed them in my black studies class, but what usually happens is that the class eventually decides that they’re going to be part of the movement against the word nigger. Once they understand what the history is and what the word means, they stop using it and they encourage their friends to stop using it.”

“It is about choices,” I say, feeling guilty for a lot of reasons before she demurely stops me.

“Yes, it always is,” she says, “about choices.”

Just being a Negro doesn’t qualify you to understand the race situation any more than being sick makes you an expert on medicine. Do you agree with this? I get what he’s saying but I think, on some deep level, the analogy is facile. I don’t necessarily agree with it. The quote I like more is from Toni Morrison. She said, “I can’t be the doctor and the patient.” That makes more sense.

—Dick Gregory

Tamra Davis, the director of Half Baked, is feeding her children, so she can’t say out loud the last lines of the movie she directed. These are lines she had to fight for, and, along with Brennan and Chappelle, she had to try to convince fifteen studio executives that they deserved to be in the movie. She tries to talk around the lines, but finally she whispers, “I love weed, love it! Probably always will! But not as much as I love pussy!” She giggles. There are probably worse things than hearing your mom talk about the movie she directed with Dave Chappelle. Tamra Davis is nonchalantly cool, despite having the distinction of having directed the early movies of Adam Sandler (Happy Gilmore) and Chris Rock (CB4). She grew up in California and has been around comedy all her life. Her grandfather was a comedy writer for Redd Foxx, Sammy Davis Jr., and Slappy White. She understands comedy instinctually, and knows that the difference between a writer and a comic is the energy and love a comic must bring to the stage, to the audience.  You talked to some really interesting people. Who, aside from Chappelle, wouldn’t talk to you? Paul Mooney, Louis C.K. and I couldn’t find a connect to Chris Rock. Also, Bill Cosby wouldn’t talk to me. I pursued him for three months, the entire time. There was no brotherly love shown to this Philly girl by Cosby. He was my imaginary dad, too, growing up.

Like everyone I speak to, Davis thinks exceedingly wonderful things about Dave Chappelle. The man has a hagiography; I hear it from everyone: from Neal Brennan to a former executive of Comedy Central, who tells me, “I have so, so much respect for Dave. He is a great guy.” For all the bridges he has supposedly burned, Dave Chappelle is beloved. Tamra Davis is the most direct. “I just really think his voice is an important voice to be heard. I’ve spent my life working with young people who all of a sudden get launched into an incredible position of celebrity and fame and it’s very, very difficult to handle. And people handle it in different ways. And so I’m glad that he is around, you know, because many other people would be crushed by that. Having to have that inner dialogue in your head, knowing that everybody is talking about you. It’s a very difficult thing to have to navigate.”

What separated Dave Chappelle not just from Neal Brennan but also his fans is that he was suddenly vaulted into the awkward position of being the world’s most famous interlocutor in a conversation about race—the one conversation no one likes having. Yes, it is hard to look back. But it’s easy to understand why Chappelle was done with being misread, tired of explaining, finished talking. As Brennan, and then everyone else, told me: the man turned down fifty million dollars. You will never get him to speak with you.

“Beware, my body and my soul, beware above all of crossing your arms and assuming the sterile attitude of the spectator, for life is not a spectacle, a sea of griefs is not a proscenium, and a man who wails is not a dancing bear.”

—Aimé Césaire, Notebook of a Return to the Native Land

When a chance came to visit Yellow Springs, I had no expectation that Chappelle would be there. But I wanted to see it. In Yellow Springs, I met Yvonne Seon. We had a good time. We discussed my wedding, we discussed Michelle Alexander’s The New Jim Crow, and she introduced me to her family. It was a lovely day. Idyllic, even. On my way out of town, I felt tired, so I stopped for some coffee at a local coffee shop. As I was paying, I saw a few guys out back in the garden, talking, and then I saw Dave Chappelle, in a weird white tank top that strained to contain his muscles. No longer lean. Well-defended.

So at a cash register in Yellow Springs I stood and watched as the person I had so badly wanted to talk to walked toward me. But when he said hello, I made a decision that—until my plane ride home—I kicked myself for. Moving on pure instinct, I simply said hello, turned and finished paying my bill, and left.  This decision of yours–to let him go, as it were–was quite contentious! “There was no conversation to have,” you told Longform, because Chappelle had already declined to do an interview. “The point is he’s stated all he needs to say.” Is this the difference between being a reporter and an essayist? I think a reporter would be obligated to be, as you put it to Longform, a pest, while the essayist has the freedom to stay back. But is the reporter obligated to find things if they already know the answer? Plus, I don’t think the story needed it. You need to respect people’s autonomy and their ability to make decisions for themselves. It’s a comment on the entire history of black people in America. We haven’t had autonomy and ownership of things. Here was someone who had ownership of all that stuff, and didn’t have any reason to return again. I don’t think I wanted to see Dave Chappelle, the person who wanted to be pestered; I wanted to see Dave Chappelle, the person who wouldn’t talk to me. And that’s what I got. I was pretty satisfied with that.   As soon as you saw Chappelle, did you know that was going to be the end of the piece?   Yeah, I did know. I knew when I went out to Yellow Springs, that what are the chances of me seeing Dave Chappelle? I literally just went to have lunch with his mother. I just found her so amazing. It never crossed my mind that I might see Dave Chappelle and it never crossed my mind to ask her to meet him. We never talked about him. So when I saw him, I thought, “Oh, my god. This is crazy. You’ve been looking for this person for three or four months now.” And here this guy is, just walking down the street. Do you know what that is like? That was cray-zee. I knew for months that I just needed him in it. And then the dude walks by in a tank top and a backpack. He’s fucking buff, too. It was weird as shit. It was weird to catch up with him ten years later and he looks like The Incredible Hulk in mocha. I have one more thing to tell you, because this is the last interview I’ll ever do about this piece, so I’ll let this one out. When you see the person you’ve been reading about–thinking about, talking about; almost living, eating and breathing them–just walk down the street, it’s incredible. I went to get the coffee and he just walked right by. And he actually said, “Hello.” In that moment–which was kind of Negritude; that is what my mom calls it when black people see each other, we know instinctively to always say hello–I knew I could’ve said, “Hey, I just had lunch with your mom,” or “Hey, I’m working on this piece.” But as soon as it happened, it was over. And he kept living his life. And that, to me, in my gut, that was the end. I got the right thing. So then I’m flying out of Dayton on this small plane, and I’m sitting next to this guy and we’re talking. And he ends up being Dave Chappelle’s best friend in Yellow Springs. And that’s when I really knew I had done the right thing. I knew it was all good. Finally, the other thing is, Dave Chappelle did a show at Radio City Music Hall and I got backstage passes from Richard Nichols. Rich was always looking out for me. So my husband and I are going backstage because there was a break between shows. And I knew that I might see Dave Chappelle and I was going to tell him that I’d written this long piece about him. And I was so excited to let it all bleed. There’s a scene in Chappelle’s Show about what if everything was in slow motion. So we were walking backstage and, all of a sudden, I see Dave Chappelle coming towards me. He’s carrying a bottle of Veuve and security is around him. But I have my pass and I’m feeling emboldened, so I get ready to talk to him. Then suddenly a big hand goes pssshhhewwww! We’re not small people but we were cleared the fuck out! Which is exactly what he does in that skit, he imagines being cool enough to do that to people. And I thought, anytime you get to make a skit like that come to life, just keep on truckin’, brother. So I’m still searching for Chappelle, ten years later.

Did I mention that the light is beautiful at dusk in Yellow Springs? The people walk the streets, going to the grocery store or looking at the theater listings. There is a café that was once a house on the Underground Railroad that now serves delicious Reuben sandwiches and plays disco music. People say hello in passing, kids with Afros zip by on scooters. It is small-town America, but with hemp stores. I didn’t want to leave, because it seems like an easy place to live. Not without its problems, but a place with a quiet understanding that conversation is the minimum for living in a better world. You know, simple things.

At a memorial for his father a few years back, standing next to his mother at the podium at Antioch College, Dave Chappelle ended his speech by thanking the community of Yellow Springs. “So,” he said, “thank you to you all for giving my father a context where he could just exist and be a good dude, because to be a good dude, as many good dudes have shown you before, is just not a comfortable thing to be. It’s a very hard thing to aspire to. And so thanks for honoring him, because sometimes it is a lonely, quiet road when you make a decision to try to transcend your own demons or be good or whatever he was trying to do here.”

In my car’s rearview mirror, it doesn’t seem strange to me at all that I am watching America’s funniest comic standing in a small town, smoking cigarettes and shooting the shit with his friends. Like everyone else on the street, one friend is white, the other is black—the only difference being that they are with Dave. But here Dave is just Dave. Totally uninterrupted, unheckled, free to be himself, free to have a family, and land, and time to recover. Time to be complicated, time to be a confessed fan of fame who one day decided that it was important to learn to be himself again. Chappelle took a drag on his cigarette, and laughed, and it was apparent that he was doing what he said he wanted most in life: having fun and being funny. So, for better or for worse, I took this to be my answer.

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