How Dave Chappelle Fights the Culture War From the Stage

There was a time I thought he was the best living comedian on Earth. I'm not sure anymore. He's attacking easy targets and going for easy"low hanging fruit". Is he thought provoking and breaking new ground? Not like he did in the past.

I hope his new Netflix special is a turn for the better. Thus far I've been underwhelmed by somone who's capable of hitting home runs.

Would he do this today? He's too "chicken" to really challenge the progressive narrative.

How Dave Chappelle Fights the Culture War From the Stage

Chappelle sold more tickets in the past year than any other comedian despite repeated controversies and blowback. Now he’s planning to open his own comedy clubs.

Dave Chappelle is one of the most popular comics of the 21st century. In recent years, he has also become one of the most polarizing.

By John Jurgensen, WSJ

Dec. 28, 2023 12:30 pm ET

In the packed sports arenas that Dave Chappelle performed in around the country this year, his stage was situated at the center of the floor so he was surrounded on all sides by his people.

“Here we are to laugh at the stuff we’re not supposed to laugh at anymore,” said Elizabeth Harborth, one of roughly 17,000 who turned out for Chappelle on a Wednesday night last July in San Antonio. A 45-year-old truck driver, she came with her daughters, both Chappelle fans in their 20s.

Followers like these have fueled Chappelle’s live shows. He brought in more money in ticket sales than any comedy act in the last touring year tracked by Pollstar, ending in mid November. He grossed $62 million for 31 ticketed shows in 2023, not including several co-headlining shows with Chris Rock and events with receipts not reported to Pollstar.

Chappelle is one of the most popular comics of the 21st century, but in recent years he has also become the most polarizing. That’s due in large part to the bits about gay and transgender people running through his series of Netflix specials. Now, the likelihood of more controversy looms with the release of a new stand-up special—Chappelle’s seventh for Netflix in six years—on Dec. 31, titled “The Dreamer.”

There’s a gap between the backlash Chappelle generates online and his live shows with legions of fans. Amid this comedy culture war, he’s doubling down and cashing in.

In San Antonio, he took the stage in a sleeveless shirt with his last name across the chest and started in on his notoriety for LGBTQ material. “That’s the old me. I’ve got a whole new show tonight. Tonight I’m going to do all handicapped jokes.” After a roar of laughter, he said, “They’re not as organized as the gays.”

The reaction to his last stand-up special, 2021’s “The Closer,” included a walkout of Netflix employees demanding (unsuccessfully) that the streamer remove it. Around that time, Chappelle started consistently hitting bigger venues than the theaters he focused on before.

Chappelle was one of the first major entertainers to make audiences put their phones in locked pouches, turning his performances into offline experiences. He smokes cigarettes throughout his sets in nonsmoking venues.

While other major comics plan tours long in advance, Chappelle often treats sports arenas more like comedy clubs. He books them on relatively short notice, knowing he can sell tickets quickly.

Chappelle is making his next career move with venues small enough to look his whole audience in the eye. He’s opening a comedy club where he lives in Yellow Springs, Ohio, and he has plans for another club in his original hometown of Washington, D.C. The latter is part of a redevelopment project in a district once known as Black Broadway. A block from the site is the century-old Lincoln Theatre where Chappelle recorded his new Netflix special in October.

As a scene-maker, Chappelle had a trial run during the pandemic summer of 2020. At a series of shows for masked audiences at a rural, outdoor pavilion in Yellow Springs, he did free-form sets and brought out surprise guests from David Letterman to rocker John Mayer. He currently has a deal with Netflix to produce stand-up specials for other comics under the banner “Chappelle’s Home Team.”

Chappelle’s impresario era is now taking shape at a former fire station in Yellow Springs. The comedy and music club bears his logo—a white “C” on a field of red, black and green—outside on a video screen. There’s still construction fencing around the brick building, its restaurant won’t open for months and the venue’s current name—YS Firehouse—could change, but Chappelle is already breaking in a performance room designed for less than 200 people.

He performed there three times over a recent weekend for audiences including locals and family. According to one attendee, Chappelle said the club was one of his proudest achievements and linked it to the village’s history as a haven for artists, free thinkers and the liberal politics of Antioch College, where Chappelle’s late father taught.

Demonstrators gather outside Netflix in response to Chappelle’s special ‘The Closer’ in 2021.

With a club on home turf, Chappelle gets a hangout magnet for his many famous peers, total control over the conditions for their comedy and a more intimate environment than cavernous arenas offer.

“Sometimes I tell a joke to thousands of people and the crowd looks at me like I’m crazy,” Chappelle said at the Enterprise Center in St. Louis last January. “But seven or eight people laugh really hard and I’ll be on stage, like, ‘Yeah, that’s good enough.’”

Chappelle’s critics say he’s been using the global platform of Netflix to hammer on vulnerable groups, harping on their supposed sensitivities and social ranking. “How the f—are transgender people beating Black people in the discrimination Olympics?” he said in the 2017 special “The Age of Spin.”

Former fans call it a fixation that damages his legacy. Chappelle defends such material, for example a “Saturday Night Live” monologue in which he discussed antisemitic outbursts by Ye, formerly known as Kanye West, as a form of artistic expression.

To his base, Chappelle has permanent credibility because of work he did decades ago. Many fans interviewed at his shows pointed to the groundbreaking sketch comedy of “Chappelle’s Show”—and his abrupt decision to quit that TV series. In 2005, he walked away from its third season and a deal with Comedy Central valued at $50 million. Later, Chappelle cited his discomfort with the way white audiences embraced the show’s raw racial satire. In his decade of self-exile from show business that followed, that chapter took on mythic symbolism for Chappelle’s followers.

“I just respect him and the way he isn’t caught up in the machine of the industry,” said 53-year-old Mark Gomez, attending the San Antonio show with his 32-year-old son. “This is all money,” he added, gesturing to the crowd filing through a concourse where there were $90 Chappelle hoodies for sale. “But it doesn’t seem like money is driving all his decisions.”

From the stage, Chappelle has described his motives for digging in on jokes that make people mad. “The more you say I can’t say something, the more urgent it is for me to say it,” he said last year in a speech at his high school alma mater in D.C.

That agenda is now part of the draw at his live shows, even for fans cautious about certain topics. “We’re hypersensitive” to Chappelle’s bits about LGBTQ people, said Meredith Martin of Tupelo, Miss., because one of her two adult sons is gay.

She and her husband, Brent, traveled to a Chappelle show in Memphis, Tenn., last January. They hadn’t yet informed their son about seeing a comic he can’t stand. “He’s in a media bubble, like the rest of us,” Brent said. “He’ll give us hell, but he’ll understand.“

“It’s just freedom,” added the 56-year-old realtor, describing his own Chappelle fandom. “I can laugh at what he says, or I can dismiss it, or I can be offended. But that’s fine, because the next thing he says will probably be funny.”

In Memphis, San Antonio and St. Louis, fans wore pristine sneakers and stylish outfits. Others sported heavy-metal T-shirts and tattoos. They were a mix of races, ages and genders that a political party would envy.

But Chappelle’s live show isn’t always a love fest. Last year, he escaped harm when he was ambushed on stage at the Hollywood Bowl by a man armed with a knife. This past October, remarks Chappelle made about the Israel-Hamas war generated news reports of walkouts and angry shouts from his audience.

He’s known for speaking seriously in his stand-up sets. At the end of his performance at Memphis’s FedExForum last January, Chappelle discussed Tyre Nichols. The 29-year-old Black man had died two weeks prior after being beaten by Memphis police. Chappelle said family members of Nichols were in the audience as he addressed the potential for violent protest in the city: “You guys are about to have a moment, and how you handle these moments is everything,” he said. “Before you destroy something, try to build something, together.”

Chappelle had begun that night with his mock promise of “all handicapped jokes.” He pretended to be a disabled person in the audience, annoyed because they wanted jokes at the expense of trans people.

Out in the audience, 19-year-old Arlo Bishop, who has cerebral palsy, was laughing. “That was the funniest part of the set,” he said later, “because I could totally relate.”

But he was disappointed with the rest of Chappelle’s performance that night. It included a long, blow-by-blow description of a sex tape starring Chuck Berry. Bishop said he and his father had gone in expecting keen social commentary or observational insights from one of their comedy heroes.

“He didn’t really make us think at all,” Bishop said, then added, “I’d give him another chance.”

Write to John Jurgensen at John.Jurgensen@wsj.com