It’s Sunday, 4 September 2022: Dave Chappelle is telling an audience of 20,000 at the O2 arena in east London how he tried to explain to his wife why he had to go back to the boxer Floyd Mayweather’s strip club in Las Vegas – why he had to make a second visit on the same night.
Suffice to say, a supposed longing for a “safe space”, a lot of cash, a fish tank and the ingestion of psychedelic chemicals are all involved in the tale. No transcription can do justice to how funny is his account of fear and fishing in Las Vegas – and his desperate subsequent attempts to pacify Mrs Chappelle – so I’m afraid you’ll just have to take my word for it.
It’s a good night for some laughs, too, as all those who follow such dreadful matters know that, the following day, Liz Truss is to be named as the new Conservative leader and Britain’s next prime minister. (What none of us knows, of course, is that the nation is also about to enter a period of national mourning following the death of Her Majesty The Queen on 8 September or that Truss’s premiership will be over barely six weeks later.)
The show is particularly special because it is a megawattage double bill with Chris Rock, another comedy legend who has filled this very venue as a solo act on many occasions. Rock is the Nijinsky of contemporary stand-up: the rhythm of his comedy, his cadence, his command of the stage, his trademark use of repeated phrases… all are perfect. You are always left gasping. How did he do that?
Yet it is Chappelle’s night, and not even Rock is challenging that assumption. Now aged 49, the man himself has taken to embracing the title GOAT: Greatest Of All Time. Why bother to pretend otherwise? Did Muhammad Ali ever hesitate to call himself The Greatest? Why, then, should Chappelle? It is – after all – true. Lenny Bruce, George Carlin, Richard Pryor, Eddie Murphy, Bill Hicks, Mitch Hedberg, Patrice O’Neal: all are or (mostly) were geniuses. But Chappelle is in a league of his own.
This, of course, remains a matter of personal opinion, and one which some will contest fiercely. But then – not to get combative – I do take the question personally. As much as I loved the September show, it meant even more to be able to take my two sons (then aged 15 and 18) to see Chappelle at the Adelphi Theatre on 2 June 2019, where he was warming up a set that became one of his six Netflix specials. It felt like a cultural rite of passage: sharing a Chappelle performance with the next generation. We had a great time, unforgettably so.
At some point in the last decade or so, I realised that Chappelle had entered my innermost imagination, as an artist whose work I could not operate without and would cherish to the grave. There are hundreds of performers and writers whose achievements I revere. But a very small group occupies a different role: Saul Bellow, JD Salinger, Toni Morrison, Wagner, the Sex Pistols, Joy Division… a few others, but not many, whom I constantly, if subconsciously, consult like inner oracles. And now Chappelle is in there, on the neural granite of this imaginary Mount Rushmore, sharing cigarettes with Johnny Rotten.
Why? To get the most obvious point out of the way: because he is preternaturally, prodigiously talented. Performing since the age of 14, when he was living in Washington DC and his mother, Yvonne, used to drive him back and forth from gigs, Chappelle has, over many years, developed unrivalled comic muscle memory.
There are hundreds of performers and writers whose achievements I revere. But a very small group occupies a different role, whom I constantly, if subconsciously, consult like inner oracles. And now Chappelle is in there.
He put in his time (and then some), not truly breaking through to public consciousness until his unforgettable cameo in The Nutty Professor (1996) as Reggie Warrington, a manic comedian who brutally roasts Professor Sherman Klump (played by Chappelle’s idol, Eddie Murphy), seated miserably in the audience on a date with Carla Purty (Jada Pinkett).
Two specials – Killin’ Them Softly (HBO, 2000) and For What It’s Worth (Showtime, 2004) – considerably enhanced his international reputation, not least when the highlights started proliferating on YouTube. He seemed able to make anything funny: how white people talk to cops (“Sorry officer… I didn’t know I couldn’t do that”); the difference between grape juice and grape drink; why Michael Jackson was an under-appreciated host; meeting a Native American in a Walmart superstore (“Are you a hunter-gatherer?”); his plans for testicular cosmetic surgery; and why terrorists never take Black people hostage (Isis on the phone to the White House: “Hello? We have got five Black… Hello?”).
Yet it was Chappelle’s Show (2003-2004), his two-season sketch series for Comedy Central that truly sealed the deal. The show featured a roster of regular characters: notably Clayton Bigsby, a blind white supremacist unaware he was actually Black; the crack addict Tyrone Biggums; and cocaine dealer Tron Carter, who was always pleading “the fif” (Fifth Amendment) to avoid saying anything incriminating in court.
All of which was standard enough for a sketch series. What sent Chappelle’s Show into the stratosphere was the readiness of its star to rip up the rules and try something new. In particular, he devoted an entire episode to the reminiscences of cast member Charlie Murphy (Eddie’s late and much-mourned brother) about the funk superstar, Rick James. The somewhat addled James was also brought in to recount his own version of events and of the fights that Murphy claimed that he had had over the years with his great friend Rick – played by Chappelle in the dramatised sequences. The episode has rightly entered comedy folklore as one of the funniest half hours ever recorded. It brilliantly satirised James’s casual misogyny (“I’m Rick James, bitch!”) and also spawned the unlikely T-shirt slogan “Fuck yo couch”.
Though Chappelle’s Show was initially hard to see outside the US – this was long before streaming channels, remember – the series proved a worldwide hit on DVD, and the comedian finally achieved something close to global reach. Not surprisingly, Comedy Central wanted to lock in Chappelle for more of the same, and put $50 million on the table as an incentive.
He walked away. Turning down the biggest deal in the history of television comedy, Chappelle headed to South Africa to escape the mayhem he knew would ensue, and to avoid the worst of the gossip about his decision – which was regarded in the tightly knit entertainment industry not only as deeply irrational, but also a despicable act of mutiny. It was insinuated that Chappelle had gone mad, developed a crack habit or that his Muslim faith had turned fundamentalist – sometimes all three.
It looked as though F. Scott Fitzgerald’s line about “no second acts in American lives” might turn out to be true. Chappelle returned to the US, Comedy Central broadcast an awful third season of his show without his participation, mainly cobbled together from outtakes, and the comedian looked set to live in semi-retirement with his family in Yellow Springs, Ohio.
Martin Amis has observed that “most writers need a wound, either physical or spiritual”. A broadening of this thesis might be that cultural figures can grow to a sometimes colossal extent if they recover from an apparently definitive setback – and somehow get back on the spotlit horse.
I don’t mean Take That reuniting for an album and a tour. I mean Elvis storming back with ferocious rock’n’roll menace in the NBC Christmas special of 1968. I mean Ali refusing the draft, being stripped of the world heavyweight title in 1967 – and then winning it back seven years later with his astonishing defeat of George Foreman in the “Rumble in the Jungle”.
Chappelle has never disclosed fully why he walked away in 2005, but the snippets he has offered amount to something close to an answer – and help to explain why the decision was such a formative experience. In an interview with David Letterman in 2020, he revealed that seeing a Chappelle’s Show crew member apparently laughing at him, rather than with him, during the recording of a sketch had strengthened deeper anxieties he had already been feeling.
“It just raised an interesting question to me, which I was already wrestling with in the first place,” he said. “The sketch wasn’t that bad. It’s actually funny. It was a pixie. It was me dressed in blackface, who’d pop up anytime a person felt the pains of racism, which is a tough trick to pull off. It’s not a bad sketch, but hearing the wrong laugh, while you’re dressed that way, it makes you feel shame.”
Fourteen years before, in an episode of Inside the Actors Studio hosted by the late James Lipton, he had attacked the entertainment system more generally, referring to the apparent breakdown of his friend, the comedian and actor Martin Lawrence:
What is happening in Hollywood that a guy that tough will be on a street, waving a gun, screaming: “They are trying to kill me”? What’s going on? Why is Dave Chappelle going to Africa?… A weak person cannot get to sit here 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. “I don’t understand this person, so they’re crazy.” That’s bullshit. These people are not crazy, they’re strong people. Maybe their environment is a little sick.
So when, in 2016, it was announced that, after more than a decade of partial obscurity, Chappelle was returning with a $60 million Netflix deal, the big question was: why? The lure of the money had to be a significant factor: Chappelle was quite open about how much he valued the freedom that this level of financial security gave him. For one thing, it enabled him to produce The Midnight Miracle: a series of near-perfect, often contemplative podcasts with his friends Talib Kweli and Yasiin Bey as co-presenters, which has now been transferred to vinyl. He could finance his own films, too.
But there was more to it than that. No accident, I think, that Chappelle chose to make his return in the very year that everything went haywire, and the ground shook beneath our feet as Donald Trump captured the White House, Brexit sent tremors far beyond these shores and the world became one great cultural warzone.
This was a new Chappelle for new times, too. Previously lanky and artful with his physical awkwardness, he had bulked up in the gym; he stood still more often, drawing with a natural aristocracy upon his cigarette or vape; and the material – though still full of scabrous jokes about sex, human foible and the joyous absurdity of day-to-day life – had taken a sharp turn away from the spirit of the sketch show.
Watch, for starters, his extraordinary short film 8:46 (available on YouTube), which was recorded at the Wirrig Pavilion in Yellow Springs on 6 June 2020, deep in the pandemic, with a socially distanced audience of only 100. A mere 12 days had passed since the murder of George Floyd in Minneapolis – and Chappelle did not hold back:
This man [convicted former police officer Derek Chauvin] kneeled on a man’s neck for eight minutes and 46 seconds. Can you imagine that? This kid thought he was going to die. He knew he was going to die. He called for his mother. He called for his dead mother. I’ve only seen that once before in my life. My father on his deathbed called for his grandmother. When I watched that tape, I understood: this man knew he was going to die. People watched it. People filmed it. And for some reason, that I still don’t understand, all these fucking police had their hands in their pockets. Who are you talking to? What are you signifying – that you can kneel on a man’s neck for eight minutes and 46 seconds and feel like you wouldn’t get the wrath of God? That’s what is happening right now. It’s not for a single cop. It’s for all of it. Fucking… all of it.
Chappelle’s righteous rage is quite something to behold. He is still a comedian, at least by profession. But, in this remarkable monologue, he is using the comedian’s platform to make a point about a deplorable injustice, and doing so with formidable, hard-earned power. Precisely because we were used to him joking about smoking weed with white people, the challenges of dating orangutans, and the intrinsic humour of Mexican food, the punch of his eloquent rage made all the more impact.
It was no accident, I think, that Chappelle chose to make his return in the very year that everything went haywire… as Donald Trump captured the White House, Brexit sent tremors far beyond these shores and the world became one great cultural warzone.
This time he evidently had a lot he wanted to say. That much was clear from the Netflix specials, which were both hilarious and seriously controversial.
In particular, his jokes about the trans community embroiled him in a series of rows that have yet to be truly resolved. Chappelle’s defence was that he makes fun of everybody and everything, that he had always liked trans people and that he had, in particular, formed a close friendship with Daphne Dorman, a trans comedian who killed herself in 2019. Her story forms a significant part of his most recent Netflix special, The Closer.
Dorman had backed Chappelle online only a few weeks before taking her own life. Her family remained supportive of him after her death. But the argument over The Closer spiralled into seething social media anger, vilification of Chappelle as an alleged “transphobe” and even a protest outside Netflix’s headquarters in Los Angeles.
Chappelle’s point has always been specific and related to the pecking order in modern “intersectionality”: the belief that inequalities based on race, sex, sexual orientation, gender identity, disability, class all interact and “intersect”. Common sense, you might think. But who gets the first bite at the social justice cherry? Here’s what he had to say in The Age of Spin (2017):
I was like, “How the fuck are transgender people beating Black people in the discrimination Olympics?” If the police shot half as many transgenders as they did n——- last year, there’d be a fucking war in LA. I know Black dudes in Brooklyn – hard street motherfuckers – that wear heels just to feel safe.
In Equanimity, released by Netflix in the same year, Chappelle warmed to his theme:
I cannot shake this awful suspicion that the only reason everybody is talking about transgenders is because white men want to do it… it reeks of white privilege. You never asked yourself why it was easier for Bruce Jenner to change his gender than it was for Cassius Clay to change his fucking name?
Questions like this can reduce a comedy club to silence (“Why is it so quiet in here?” as Bill Burr likes to say when he tackles tricky themes). But Chappelle’s position is that stand-ups are obliged ex officio to take these risks; to rush into disputed and uncomfortable territory and, using the excavation tools of humour and irony, to dig for the truth.
And especially so at this particular moment in history, at a time when all artists and writers are being urged to consider very carefully the “offence” they might cause, the “safety” of others, and the supposed “harm” that their work can allegedly inflict. As Chappelle said in The Bird Revelation (2017), addressing his fellow comics: “More now than ever… you have a responsibility to speak recklessly. Otherwise, my kids may never know what reckless talk sounds like.”
In the era of cancel culture, “safe spaces”, “sensitivity readers” and (worst of all) pre-emptive self-censorship, it is hard to think of a more counter-cultural stand to take: not only to defend “reckless talk” but to insist upon it. Not, as the comedian puts it, to yield to the demands for silence from those of “brittle spirit”, but to exercise the right to speak without fear or favour.
All of this, I think, has been quite strategic. It is no accident that Chappelle’s favourite book is the autobiography of the great Black abolitionist Frederick Douglass (1818-1895), who understood that free speech is the most precious guarantor of the rights of the oppressed. “Liberty is meaningless,” said Douglass in 1860, “where the right to utter one’s thoughts and opinions has ceased to exist.”
Chappelle came back from semi-retirement because he sensed – correctly – that he truly had something distinctive to offer in the age of populism, so-called “wokery” and the blazing heat of the culture wars. More to the point, he intuited that the art he had mastered, that of the stand-up comedian, was equal to the task, and that the role of truth-teller and story-teller – what, in African tradition, is called the griot – had acquired a new significance in the screaming Babel of the 21st-century digital landscape.
In his acceptance speech for the 2019 Mark Twain Prize for American Humor, he referred directly to his calling as a griot, and also had this to say:
Stand-up comedy is an incredibly American genre… Each and every one of you have a champion in the room. We watch you guys fight, but when we’re together we talk it out… There’s something so true about this genre when done correctly, that I will fight anybody that gets in a true practitioner of this art form’s way, because I know you’re wrong. This is the truth, and you’re obstructing it. I’m not talking about the content, I’m talking about the art form. Do you understand? Do we have an agreement?
But why now? Why does stand-up of this calibre suddenly seem so important and so precious? And why, for that matter, are philosophers and cultural theorists suddenly starting to analyse a stand-up comic? (As part of my research for this piece, I read a collection of scholarly essays published in 2021, called Dave Chappelle and Philosophy, edited by Mark Ralkowski, a professor at George Washington University. No, seriously.)
At base, the answer is simple, and Chappelle nailed it in his bravura 8:46 performance:
It’s serious. The only reason that people want to hear from people like me is because you trust me. You don’t expect me to be perfect. But I don’t lie to you. I’m just the guy. And I don’t lie to you. And every institution, every institution that we trust… lies to us.
That’s it. That’s all it is. Whom do we trust in 2022? One by one, trust in all our institutions has tanked. We don’t trust what we read, see and hear online, frequently with good reason. We don’t trust politicians, the police, the courts, the media, the corporations and sometimes even – most depressingly – scientists. Our reflex to mistrust is now so honed and so easily triggered that many, many millions of people preferred to remain unvaccinated, even as new Covid variants were springing up in the world’s death zones.
But – as it happens, and unexpectedly – we do trust stand-ups; and one in particular. He is the most important humourist since Twain. He is the most fearless, and sometimes divisive cultural icon since Ali. He incarnates a spirit of comic obduracy that can, if we’re lucky, play a part in saving a decadent civilisation from itself.
Every time I hear that somebody is trying to cancel Dave Chappelle, or ban one of his films, or silence him – well, a part of me comes back to life. Because he isn’t going anywhere, thank God. Because laughter is always the best vector for the bitter medicine of the truth. And because, damn it, this is no time for timid talk. Just look out the window – and be grateful for the reckless genius of the GOAT.
Matthew d’Ancona is an editor and partner at Tortoise.
Portrait Robyn Twomey / Redux / eyevine
This piece appeared in the Tortoise Quarterly, our short book of long stories. If you were lucky enough to grab a Founding Membership back in the early days of Tortoise, you’ll receive your copy in glorious, old-fashioned print. If not, you can pick up a physical copy in our shop at a special member price.