Searching For Dave Chapelle Ten Years After He Left His Own Show

Discussed: Ohio’s Rolling Farmland, Hippies in Tie-Dye, Paul Laurence Dunbar, Kanye West, Oprah, A Simpler Way of Life, Seventy-Year-Old Comparative Literature Professors in Birkenstocks, Negritude,Thurgood Marshall, Black Activism, Patrice Lumumba, Stepin Fetchit, Richard Pryor, Dick Gregory, Mark Twain’s Pudd’nhead Wilson, Hemp Stores, Reuben Sandwiches, Dusk in Yellow Springs

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 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 kindsâ€"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.

From above, everything seems smaller and less complicatedâ€"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 leadersâ€"Oprah Winfrey, Bill Cosby, and othersâ€"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 Harrietâ€"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. 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 know you must be doing something right if old people like you.

â€"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. “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 friendsâ€"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.

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. 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 toâ€"and kept him inâ€"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 townâ€"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 lifeâ€"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 culturallyâ€"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 responsibilityâ€"were interests deeply informed by his parents. 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. “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, 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.

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” sketchâ€"the unforgettable short mockumentary about a blind white supremacist who does not know he is black.

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.)

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 thereâ€"a man who was being mourned by Malcolm X and Che Guevara, whose death incited outraged protests all around the worldâ€" 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 inpost-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.”

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 dayâ€"statistically speakingâ€"there’s not one poor white person in Washington.” 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, manâ€"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!”

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.

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 postâ€"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, 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 beâ€"a man without dignityâ€"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

“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 earlierâ€"without explanation to his wife, to Brennan, or to his bosses at Comedy Centralâ€"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.

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 clannishâ€"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.”

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 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.” 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.”

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 difficultly 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 postâ€"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.

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.

“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.

“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.

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 problems… Learn to play basketball, tell jokes, or sell crack. That’s the only way I’ve seen people get out.’

â€"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.”

â€"Dick Gregory, Nigger

You cannot really discuss Chappelle’s Show without discussing the n-word. 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 outlawâ€"but none of that mattered on-screen. 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 Mommaâ€"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.” 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. 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 lookâ€"a roast my sister and I endured one night at a comedy clubâ€"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.”

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 momentsâ€"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. 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 possibleâ€"for them, for us. 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 thinkâ€"” 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.

â€"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.

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 raceâ€"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.”

â€"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 thatâ€"until my plane ride homeâ€"I kicked myself for. Moving on pure instinct, I simply said hello, turned and finished paying my bill, and left.

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 blackâ€"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.