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Was Dave Chappelle Crazy, or Were We?

When the comedian vanished in 2005, he gave up superstardom and a $50 million contract. White America called him crazy. But there's another side to his story — about race, mental health and a priceless taste of freedom — that everyone seemed to miss.

Dave Chappelle was in blackface, dressed in a bellhop costume and holding a cane. He’d just gotten done performing a “coon dance,” when the sound of a white man’s laughter echoed loud and long throughout the soundstage where Chappelle was shooting an episode of his wildly popular Comedy Central series Chappelle’s Show. It was the laugh Chappelle never expected. But it helped make up his mind: It was time to quit his show, no matter the fact that he’d just signed a new $55 million contract. Because for all the laughs he’d gotten along the way, his ears could only hear that one laugh from that one white man. To Chappelle, it was undeniable proof that he’d somehow lost his way. 

And so, at the beginning of May 2005, Chappelle disappeared. Not even his wife and children knew where he went. He was just gone. He needed space to think — and to not think. Following in the footsteps of one of his comedy idols, Richard Pryor, he fled to Africa to deal with the pain and confusion of being a Black man who tells the truth for a living in America. 

From the jump, Chappelle threaded the needle of racial humor in brilliant, enlightening ways. The very first episode of Chappelle’s Show famously featured a fake documentary about Clayton Bigsby, the leader of a white supremacist hate group who didn’t know he was Black because he was also blind. The second season included a skit about a 1950s-era white family called “The Niggars.” Chappelle could even turn Rick James into a classic trickster character of minstrel show lore yet never have it seem overtly racist. The same for a sketch that sent a group of time-traveling, Jheri-curled, lime-green-gator-wearing 1970s pimps back to the Antebellum South to fuck up some slave masters. He found a way for it to feel good to be a Black person laughing at a slavery joke. Chappelle could always deftly make fun of a Black person without Black people becoming the butt of the joke. 

As for the skit that ended it all — the one that featured Chappelle in blackface — it was meant to be a comic investigation of how Black people must navigate stereotypes, every day, everywhere, and how sometimes this costs us not just job promotions, but also dumb little things, like our favorite foods. It’s a moment most white people are likely to never know.

The sketch opens with Chappelle on a plane. The flight attendant asks him if he’d prefer the fish or fried chicken for his in-flight meal. He wants the chicken, but he also doesn’t want to be a stereotype. With a poof of smoke, a tiny pixie in blackface (also Chappelle) appears on the seat-back in front of him. “Whoo-whee!” the blackface pixie howls. “I just heard the magic words: chicken! Go on and order you a big bucket, nigga, and take a bite. Ya Black motherfucker!” 

Chappelle reacts in horror at his own internalized racism as the pixie does a celebratory “coon dance.” As Chappelle explained to Oprah in 2006, in his first televised interview after returning from Africa, “The premise of the sketch was that every race had this racial pixie, like, this racial complex. But the pixie was in blackface. Now, blackface is a very difficult image. But the reason I had chosen blackface at the time was because this was going to be the visual personification of the N-word. It was a good spirit of intention behind it. But what I didn’t consider was how many people watch the show and how the way people use television is subjective.”

Oprah listened in her very Oprah way, and nodded, adding that she knew exactly what he meant, but warmly urged him to finish his point. “When I’m on the set, and we’re finally taping the sketch, somebody on the set that was white laughed in such a way — I know the difference of people laughing with me and people laughing at me,” he told her. “And it was the first time I’d ever gotten a laugh that I was uncomfortable with. Not just uncomfortable but, like, …Should I fire this person?”

* * * * *

In 1976, three years before Richard Pryor took his fateful trip to Africa, he gave an interview to a Cleveland newspaper reporter. She asked why his comedy was so provocative, so offensive. Pryor responded simply: “I don’t know if I like to shock people, as much as I like to get to them. Touch them.” To help her understand his intent to connect, he added, “I read somewhere that if you tell people the truth, you’ve got to make them laugh, or they’ll kill you.” 

The Irish playwright George Bernard Shaw said that, and just like Pryor before him, Chappelle also knew that, for a Black comedian, if you tell them the truth and make them laugh, they still might kill you. As proof, Chappelle often cites the fact that, in 1997, Martin Lawrence, another of his heroes, was once driven by the madness of racism to the point that he stood in a Hollywood intersection in his underwear and claimed he was a Jedi knight, yelling, “They are trying to kill me.”

Chappelle’s second post-Africa televised interview after Oprah was with James Lipton from Inside the Actors Studio. During their interview, Chappelle asked the audience of students a rhetorical question, “What is happening in Hollywood that a guy that tough will be on the street, waving a gun, screaming, ‘They are trying to kill me!’? What’s going on? Why is Dave Chappelle going to Africa? Why does Mariah Carey make a hundred-million-dollar deal and take her clothes off on TRL? A weak person cannot get here and sit and talk to you. Ain’t no weak people talking to you. So what is happening in Hollywood? Nobody knows. The worst thing to call somebody is crazy. It’s dismissive.”

When he left his show, it was widely reported that Chappelle had himself gone crazy — that he was on drugs, and that somehow he’d lost his mind. But if people had been paying attention, if cultural memories were longer than five minutes, those same people would have recognized that when Chappelle quit his show, he was doing exactly what he said he would if he were ever tempted by $50 million.

It was January 20, 1998, the eve of the premiere of Half Baked, and he was on Late Night With Conan O’Brien to hype his new film. The two sharp-minded comedians bantered, and at one point, O’Brien complimented Chappelle for how he approaches comedy. Chappelle explained that he likes to mix the philosophical with the small details of life. As an example, Chappelle raised a question, one that he said works well to amuse people at parties: “Would you rather have $50 million or a magic carpet that, you know, works?” 

O’Brien didn’t hesitate; he picked the money. With childish enthusiasm, his sidekick Andy Richter said he’d pick the magic carpet. Chappelle named Richter the winner. O’Brien protested, as Chappelle explained why it’s always better to take the magic carpet than the $50 million. He concluded by saying, “Forget the money, think how much booty you could get with a magic carpet.”

O’Brien conceded sarcastically, “No, that’s a good point, because who’d come around offering up booty to someone with $50 million?”

“That — that will run out,” Chappelle cautioned him in return. “You have to compete with other rich men. A man with a magic carpet will usually be the only person in the room with a magic carpet.”

Of course, within a few years, Chappelle would be asked essentially the same question, but for real this time. And staying true to himself, he picked the magic carpet, which, in his case, was his freedom — or his Blackness, his realness, his dignity and his soul. 

* * * * *

The Richard Pryor Show walked in 1977 so that Chappelle’s Show could run in the early aughts. Maybe the best example: Black audiences and white audiences likely laughed for different reasons at a sketch about a money-loving, hyper-sexualized, immoral Black preacher who wants to get his hands on “white folks’ money.” Backed by telephone operators like a telethon, Pryor’s preacher tries to get white folks to open up their wallets and purses and support the Black church. He says they’re “not begging for the crippled children,” nor for “the Black orphans of Watts,” and they’re also “not begging for the Black old folks’ home either.” Pryor’s preacher explains, “This money is to go to the BTAM fund — the Back to Africa Movement.” 

As soon as he stops speaking, the phones start ringing with dozens of callers, all eager to give their “crossover bucks” to his church and send Black people back to Africa.

This idea of “going back to Africa” — not to move there the way Marcus Garvey and his Black Star Line proposed, but rather to reconnect to one’s roots — was the theme of multiple Richard Pryor Show skits, which is notable since the series only lasted four episodes. For instance, there’s one sketch about Black Americans traveling to Africa to find their roots, only to discover con men waiting for them with the promise of a connection to their history, which they can purchase as a tour. Pryor calls his sleaze-bag African character the Mr. Come-From Man. He will tell you where you come from. A biting joke to be sure, but it’s not meant to make fun of Black people for having the desire to reconnect to Africa, but rather for getting hoodwinked by the kind of greed they should expect in any group of humans. 

When Chappelle first left the U.S., he didn’t plan to go to the Motherland. Originally, he wanted to travel to Saudi Arabia, to go to Mecca and perform the hajj, the religious pilgrimage required of all able-bodied and financially-capable Muslims. But since his escape-from-America plan was formulated last minute, he didn’t have the necessary visas and paperwork; famous or not, he just couldn’t get into Saudi Arabia. So he flew to South Africa to visit family friends, like a low-key hajj; it was a pilgrimage to his community. 

Chappelle recalled that change in plans during his Inside the Actors Studio appearance. “I don’t necessarily practice the way a good Muslim is supposed to practice,” he joked. “But I believe in these tenets. And in Africa, there’s a small community of people that don’t know anything about the work I do, and they just treat me like I’m a regular dude. So I knew that in Africa I’d have a place to sleep, and that I wouldn’t have to feel strange, and you know, where they wouldn’t call me crackhead and all these things they said in the country where I’m from. In Africa, they didn’t know anything. They was feeding me, and taking care of me, and taking me to the mall, and just regular stuff. It just made me feel good. It reminded me that I was a person, you know.”

After being returned to a sense of normalcy, Chappelle reached out to his wife and family back home. “Then I called home, and people be like, ‘Oh my God, are you all right?’ ‘Yeah, I’m just chillin’. I’m in Africa, baby. What’s going on?’ And then I got a call from a journalist that had been working on a story, and he was like, ‘Yeah, rumor mill is going on about ya. I just wanna clear a few things up, and I’m like, ‘Yeah, what’s going on?’ ‘Do you smoke crack?’ I said, ‘What?!’ ‘Did you graduate from high school?’ It was all these crazy questions, and I thought about never coming back. I said this place is crazy.”

What brought Chappelle back to this crazy place — what helped him see America as his home, and a place worth fighting for — was Pryor. Chappelle told that same audience of acting students how the ethos of Pryor’s comedy convinced him to return home, and pushed him to get back up onstage and do what he does best. 

“You know, those like evolution charts? He was the dude walking upright,” Chappelle offered. “Richard was the highest evolution of comedy. There was an article I had read after he died. It said it best: ‘The mark of greatness is when everything before you is obsolete, and everything after you bears your mark.’ And what a precedent he set — not just as a comic, but as a dude. The fact that someone was able to open themselves wide open like that. It’s so hard to talk in front of people, or to open yourself up to your closest friends, but to open yourself up for everybody. ‘Yeah, I free-base, I beat my women, I shot my car,’ and nobody’s mad at Richard for that — they understand. And when I was going through this thing this year, that is the example I would think to myself, that gave me the courage to just go back on the stage.”

Both Black men wanted to be funny but without losing their dignity, to be honest without losing their mind and to be successful without losing their soul. Both men’s work is solid evidence of how comedy helps bring about social change just like more serious-minded Civil Rights workers. Like the Freedom Riders, Chappelle and Pryor also demanded equality, and did so with dignity and respect for Black people, as we continue to struggle to make America see and affirm our humanity.

Like Chappelle, Pryor often spoke openly about the intersection of racism and entertainment. In an interview with reporter Bill Boggs, he was asked, “What do you think these executives are afraid you’re going to do to White America?”

“Uh, probably stop some racism,” Pryor responded.

“Stop racism?” Boggs retorted, incredulously.

“Yeah,” Pryor said with a nod. “They’re probably afraid of that, because then if people don’t hate each other and people start talking to each other, they find out who’s the problem.”

“Which is?” Boggs followed up.

“Um, greedy people,” Pryor answered, straight-faced, no joke in his answer. 

“Do you really think that some of the guys that you dealt with at NBC — no names, right, because there’s lawsuits for that, too — that some of these guys really want to promote racism? Actively, or is it a subconscious thing?”

“I just think it’s part of capitalism to promote racism, right? In order to make things work. If you feel better because you’re white, and you can get a job, you use that, you know. I mean, I would.”

In 1979, after Pryor’s wife “hauled him out of a house full of hookers and drugs,” the comic’s therapist suggested that he get out of American and go to Africa. Taking the advice to heart, Pryor hit up Kenya. He was overcome with what he found there: “The only people you saw were Black — at the hotel, on television, in stores, on the street, in the newspapers, at restaurants, running the government, on advertisements. Everywhere.” 

As he reflected on how it felt for him to see a world made by and run by Black people, Pryor had an awakening, telling his wife, “You know what? There are no niggers here. … The people here, they still have their self-respect, their pride.” 

This thought led to Pryor’s most famous epiphany, which he discussed in his autobiography Pryor Convictions, when he wrote about his past use of the N-word: “To this day I wish I’d never said the word. I felt its lameness. It was misunderstood by people. They didn’t get what I was talking about. Neither did I. … So I vowed never to say it again.”

After he returned to the U.S., Pryor was better, healthier, but he wasn’t healed. It doesn’t work like that. Africa isn’t Wakanda; it’s not a magical place. Nor is it able to single-handedly cure generational trauma and systemic racism. Case in point: Within two years of reconnecting with his deeper self in Africa, Pryor decided to light himself on fire. 

According to his bodyguard, the two men were watching a documentary about the Vietnam War, and Pryor was inspired by the unflinching conviction of a Buddhist monk who self-immolated in protest of the war and American imperialism. When his bodyguard left the room, Pryor doused himself with three-quarters of a bottle of 151 rum, grabbed a lighter and set himself ablaze. His bodyguard recalled a ball of fire running past him. Despite having only a one in three chance of surviving the third-degree burns over 40 percent of his body, somehow Pryor survived. 

For Chappelle, a young boy in Washington, D.C., at the time, Pryor became a cautionary tale. He showed Chappelle that if Chappelle wanted to follow in his footsteps, he needed to always be sure to spit fire, otherwise it might consume him. 

* * * * *

“You disappeared for a while. People were saying, ‘Where’s Dave? Where’s Dave Chappelle? Where’s he gone?’ It turns out you took a trip to Africa, is that true?” Conan O’Brien asked Chappelle during a guest appearance in 2006.

“Yeah, it’s true. It wasn’t like they said,” Chappelle explained.

“Because the stories were, like… Because the stories, as you know, you were hearing all kinds of stuff on the news,” O’Brien continued.

“It was crazy, man,” Chappelle marveled. “First, I went to Africa to chill. I’ll tell you, you hear a lot of Black people say this — when you go to Africa, especially your first time, it gives you the overwhelming feeling like you’re home, which is true. I had that feeling: ‘Man, this feels like home.’ I think I felt that way because there’s a McDonald’s in the airport.”

The audience laughed; they could see that Chappelle was officially back. “I was in Africa, and the next thing I know I started hearing about all the stories: ‘Comedian Dave Chappelle is in a mental institution in South Africa.’ And I was like, ‘Man, I must be losing my mind, because I thought this was the beach.’” 

After the audience laughed once more, after Chappelle could hear they were laughing with him, not at him, he hit the crowd with one more bit of his truth: “Maybe I know stuff that people don’t want me to talk about, or things they don’t want you to believe, so they call me crazy. But it was a weird thing to get called crazy. At first it was scary. Now I feel like it’s liberating. I feel free, like I can just say what I want to — they already call me crazy.”

A decade later, Chappelle signed a deal with Netflix for a series of comedy specials (at $20 million per special). To date, he’s released five of them, which means he’s already doubled his lost Comedy Central money (and in the process, gotten both the cash and the magic carpet ride). The specials, of course, have also caused controversy, notably for his material about trans people. To Chappelle’s view, the trans community mirrors the larger LGBTQ community (and society in general) in that white trans people have more social standing and power than Black trans people (and Black people overall). A solid example is Marsha P. Johnson, now hailed as the person who sparked the Stonewall uprising that started the modern fight for gay rights, but at that time, Johnson was largely seen as a threat to mainstream acceptance of gay people. 

But while Chappelle focuses on the racial aspects of such stories, he ignores the larger issue that Johnson’s life and work can’t be flattened to the fact that she was Black or that she was trans. Johnson was both. To only focus on a trans person’s Blackness is to deny the fullness of their humanity. Much like how racism works. Chappelle has yet to fully grasp this. He was always so far ahead of the pack when joking about racism in America, it’s unexpected to see him fall backwards for the same reason. (It also doesn’t excuse the clear cheap shots he’s taken at members of the trans community — or the myriad defenses he’s offered for Michael Jackson and Louis C.K. and his stubborn dismissal of #MeToo.)

Chappelle’s critique of the LGBTQ community is something else he has in common with Pryor. In 1977, two years before he went to Africa, Pryor was asked by his friend Lily Tomlin to come to the Hollywood Bowl to speak at one of the largest mainstream gay rights events ever. When he took the stage, Pryor didn’t tell any jokes. Instead, he decided to call out the gay rights activists and gay community for failing to show up for Black people when they needed help during the Civil Rights movement. Then he told the audience to “kiss my happy, rich Black ass,” leaving the stage to an overwhelming chorus of boos. 

That’s the other thing with speaking “truth” and “truth tellers.” They can forget that not all of their truths are universal. Some are personal. Some are shared. And some are just bigotry cloaked in “honesty” and/or “humor.” It’s vital to know the difference. Obviously, Chappelle understands very little about the trans community (or victims of sexual assault). But it’s hard to deny that as a Black man, he doesn’t understand many of the sad shared truths about being Black in America. And to escape them, if just for a moment, he had to go all the way to Africa. Because no matter the amount of money and fame that awaited him here in the U.S. — and how many times he was called crazy for leaving it all behind — it was the only place that he could feel free to just be human.