How Dave Chappelle became comedy’s cancel-proof king of controversy

Attending the first of eight London shows, some rescheduled from August, by US comic Dave Chappelle resembled a cross between entering an airport’s secure side and visiting a prison. Any phones had to be sealed in a pouch by staff upon entry and there was an additional admonition that anyone seen using one would be ejected. Plus, there was to be no heckling, penalty unspecified.

The phone protocols are becoming more standard for comedy heavyweights concerned about bootlegs, though a prohibition on heckling is unusual. But Chappelle has good reason to be twitchy. The outspoken African-American, 48, is riding high after a series of Netflix specials that have earned him $120m, but is also seemingly riding for a fall after eliciting a backlash for his latest sets.

As recently as 2019, Chappelle received the Mark Twain Prize for American Humor, presented by the Kennedy Center with the words “Dave is the embodiment of Twain’s observation that ‘against the assault of humour, nothing can stand’. For three decades, Dave has challenged us to see hot-button issues from his entirely original yet relatable perspective”.

But in the past five years, the veneration bestowed on him – exemplified by Esquire magazine describing him in 2006 as the “comic genius of America” - has been less of a done deal.

In early 2017, he was hailed by the New York Times as "an American Folk Hero", with a “unique empathy” for Americans. The mood soured at the end of that year with two Netflix specials Equanimity and The Bird Revelation. In the first set, retorting to complaints about previous transgender material, he expressed ridicule/revulsion at the idea of Caitlyn Jenner posing nude in Sports Illustrated. “Frustratingly out of touch” was the judgement of The Ringer (the Spotify-owned American pop culture website).

Yet he had advocated the right to get it wrong, telling other comics “you have a responsibility to speak recklessly, otherwise my kids might not know what reckless talk sounds like”.

Sticks and Stones (2019) won three Emmys, as well as a Grammy for Best Comedy Album. But it incurred indignation for, among things, its gags about Michael Jackson: “I know more than half the people in this room have been molested in their lives, but it wasn’t no goddamn Michael Jackson, was it?.”

Stinging about #metoo, there was a defence of disgraced comedian Louis CK – accused of sexual misconduct - and material about the LGBTQ community – “an unwritten and unspoken rule of show business ... you are never, ever allowed to upset the alphabet people”. The set “makes a point of punching down. Not everyone is applauding”, the US opinion website Vox reported.

A trans comedian – Daphne Dorman – who defended him was in turn targeted for criticism and committed suicide. Dorman is discussed in The Closer, which was made available last week, and caused more controversy, especially with its observation that someone can be LGBTQ and racist and the sympathy it shows to JK Rowling. Chappelle allied himself with “Team TERF”, using the pejorative term “trans-exclusionary radical feminists” and said: “Every human being had to pass through the legs of a woman to be on earth.”

The US pressure group GLAAD (originally the Gay & Lesbian Alliance Against Defamation) stated that Netflix had a duty to uphold its own policy in relation to “anti-LGBTQ content”. There were apparent ructions at the company itself. Jaclyn Moore, a writer on Netflix series Dear White People, went on Instagram to say: “After the Chappelle special, I can’t do this anymore. I won’t work for @netflix again as long as they keep promoting and profiting from dangerous transphobic content.”

Another Netflix worker, a software engineer Terra Field, complained that “This is not an argument with two sides. It is an argument with trans people who want to be alive and people who don’t want us to be.” Netflix co-CEO Ted Sarandos countered that the set didn’t cross the line into ‘hate’. Dorman’s sister, Becky, reportedly messaged The Daily Beast that [Daphne] “did not find his jokes rude, crude, off-coloring, off-putting, anything. She thought his jokes were funny… Why would her family be offended?”

How did Chappelle get to this vexatious point? Born in 1973, in Washington, DC, growing up in Maryland, he answered his comedy calling in his teens. He cropped up on ABC’s America’s Funniest People in 1990, telling a joke, then honed his stand-up skills in New York, gaining spots on TV, and acquiring the soubriquet “the Kid” from Whoopi Goldberg. He built up a big following via his own Comedy Central series, Chappelle’s Show, but dramatically quit in May 2005, two years after its launch, abandoning a $50 million contract.

At the time he beat a brief retreat to Africa, and later confided to Oprah Winfrey that some of the show’s output had perturbed him, especially playing a pixie in black face, whom he called the “visual personification of the n-word. Somebody on the set [who] was white laughed in such a way … and it was the first time I had ever gotten a laugh that I was uncomfortable with… I don’t want black people to be disappointed in me for putting that [message] out there.”

Untying the corporate knot at that point would still pay long-term dividends. After intermittent appearances, he made a full comeback circa 2013 and played a series of dates at Radio City Music Hall in 2014. The success of the Netflix specials put him on a global stage but has seen him scrutinised as never before.

If Chappelle was sweating uncomfortably at being in the eye of the storm on Tuesday, that wasn’t discernible from the circle of the Apollo Hammersmith, resale tickets for which had been going for over £100. The audience sounded upbeat throughout but Chappelle himself came across as circumspect rather than confrontational, tilting between material that baited outrage and batted it away.

Taking a small age to come on, after two support acts and a loud DJ playlist calculated to pump up excitement, his set ran to a cautious 50 minutes. At least he plunged straight in. “I love my country but clearly I need a break, I’ve been cancelled in America,” he purred, then mischievously rooted about for some cigarettes. “Do they call these fags, or did they get you too?” There was audible mirth at his topical nod to Superman “coming out of the closet” this week.

To the on-side multi-racial crowd he offered a putative olive-branch: “Anyone here from the LGBTQ [community] doesn’t need to worry about a thing, I still love you and I don’t blame the media shenanigans on your community at all”. Few would have found that a satisfactory means of knocking such a complex issue on the head but insinuating that everything had been blown out of proportion is still probably not far from the truth in these hysteria-prone times.

We were made privy to cursory responses rather than a considered rebuttal – this was no era-defining meditation on what was said, and/or his right to say it. Casual, offhand, he let emphatic statements slip in and then sidle off: “I started transgender genocide, that’s what they are saying. I hope that’s not true, that clearly wasn’t the point of the act. If you’re going to kill somebody, then you should watch it again and really rethink the way you saw it the first time.”

“I can’t believe I’m in trouble for the jokes I’m in trouble for,” he said elsewhere. “I thought they’d be madder about ‘space Jews’”. Anyone who has seen The Closer, and noted its outlandish riff about aliens returning to reclaim their home-planet and likening them to Jews, will understand his disbelief too. A Muslim convert since 1991, he added: “They called me anti-Semitic – I will remind you that Palestinians are Semitic people as well.” Which is no answer.

Pre-empting the idea of being cancelled, he jibed: “That wasn’t just a special, it was a letter of resignation... I got so famous, and I can’t say anything, what the hell’s the point of being famous?” That will strike a chord with many but he must know that his wealth and his fame still protects him, as it does the likes of Ricky Gervais or Billy Connolly, who has voiced his concern that these days he would be silenced by the woke mob. For a chap who can’t say anything, Chappelle doesn’t seem much stymied, mixing the relatively innocuous with the risqué.

He recounts obtaining a protection order from a tattooed white racist who attempted to make a belligerent house call, offers some mildly outre thoughts on what it takes to keep a marriage going (“cheating” is one tip), makes a light-hearted allusion to a serial male rapist (“seven came forward which means he must have raped thousands”). And he risks further brushes with his old foes thanks to a gag about requesting to use the toilet in a bar hosting a trans party in North Carolina, where use of the bathroom is subject to trans-hostile curbs.

The simultaneous shortness and slackness of Chappelle’s set suggests a canny operator, not allowing himself the opportunity to create many more difficulties but avoiding seeming risk-averse. His presentational style is effortlessly assured, and his allusions to US history and the current state of play in America offers a reality-check that indirectly sets him in the realm of the righteous. “America is very, very, very divided just like it was before the Civil War,” he explains, noting that his grandfather told him “There will be a civil war in your lifetime, now I’m looking at this s___, I can’t stop thinking the same thing.”

He can perhaps have his cake and eat it, then, pressing buttons to elicit strong reactions while also presenting that frankness as itself a means of healing wounds, the paradox of a discourse across a divide which it accentuates.

“I’ve been treated kindly by all kinds of people,” he offers at the end, reflecting on his sojourn in London and reaching for a live and let live message. Neither this nor what precedes it is marked by the kind of unvarnished originality that warrants his being put on the same pedestal at his idols Richard Pryor and Eddie Murphy. Yet perhaps such soft-pedalling is what the fretful occasion demanded. It felt like a marker not a decisive moment; a panting catch-up amid the culture wars, not a battle won. But his name is on more people’s lips than ever before.

At the Apollo until Oct 21. Tickets: viagogo.co.uk