Dave Chappelle strode onto the stage in Riyadh on October 4, 2025, and delivered a line that instantly ricocheted around the world: “It’s easier to talk here than it is in America.” The American comedian, famed for his boundary-pushing routines and frequent run-ins with so-called cancel culture, was performing before a crowd of 6,000 at the inaugural Riyadh Comedy Festival—the first event of its kind in Saudi Arabia and, perhaps, the most controversial comedy gathering of the year.
Chappelle’s performance, part of a festival running through October 9 at Boulevard City, a sprawling entertainment complex built to resemble Times Square, was more than just another gig. It became a flashpoint in a global debate about free speech, moral compromise, and the power of laughter in a country notorious for its strict controls on public expression. According to The New York Times, Chappelle told the audience, “Right now in America, they say that if you talk about Charlie Kirk, that you’ll get canceled. I don’t know if that’s true, but I’m gonna find out.”
His words, which drew whoops and applause, seemed to revel in the irony of performing political satire in the heart of a nation frequently criticized for its human rights record. Saudi Arabia maintains tight restrictions on speech, and the list of prohibited topics is long and explicit—criticism of the royal family, the state, or religion is strictly forbidden. Yet, on this night, American comedians were skewering U.S. politics in a place where, as one Saudi dental student marveled, “It was surprising to hear him talk about it in Riyadh, when just recently America canceled Jimmy Kimmel doing the same.”
The festival’s star-studded lineup read like a who’s who of Western comedy: Kevin Hart, Bill Burr, Aziz Ansari, Hannibal Buress, Louis C.K., Whitney Cummings, Pete Davidson, Zarna Garg, Gabriel Iglesias, Jim Jefferies, Jo Koy, Bobby Lee, Jeff Ross, Andrew Santino, Tom Segura, Chris Tucker, and many more. Over 50 international comedians made the journey, lured by both the opportunity and, as some admitted, the promise of significant financial rewards. One comic, Tim Dillon, claimed he was offered $375,000, while others reportedly received up to $1.6 million.
But the event’s glitzy veneer masked a deeper controversy. Critics quickly labeled the festival “artwashing”—a bid by Saudi Arabia to polish its global image through splashy entertainment, even as it continued a crackdown on dissent at home. Human Rights Watch’s Joey Shea told The New York Times, “The festival came at the same time as a crackdown on free speech, which many of these comedians defend but people in Saudi Arabia are completely denied.”
The shadow of Saudi Arabia’s past and present loomed large. The CIA has determined that Crown Prince Mohammed bin Salman approved the 2018 assassination of journalist Jamal Khashoggi, who was brutally killed in the Saudi Consulate in Turkey. Of the 19 hijackers who carried out the September 11 attacks, 15 were Saudi citizens. Saudi courts have handed down lengthy prison sentences for the mildest forms of dissent—one student was sentenced to 34 years simply for retweeting activists.
Some comedians refused to participate on principle. Atsuko Okatsuka, who declined her invitation, posted screenshots of a contract that forbade any material “that may be considered to degrade, defame, or bring into public disrepute, contempt, scandal, embarrassment, or ridicule” Saudi Arabia, its leaders, culture, or any religion. “A lot of the ‘you can’t say anything anymore!’ comedians are doing the festival,” she wrote on X, adding with a laugh that “they had to adhere to censorship rules to do it.”
Bill Burr, another headliner, acknowledged signing a scaled-back version of the gag order after pushing back. “Don’t make fun of royals or religion,” he summarized on his Monday Morning Podcast. “The royals loved the show. Everyone was happy. The people that were doing the festival were thrilled.” Burr admitted he expected hostility, joking, “I expected everyone to be screaming ‘Death to America’ and they’re going to have like fucking machetes and want to chop my head off because this is what I’ve been fed about that part of the world.” Instead, he described the experience as “mind-blowing” and suggested that cultural exchange could be a force for positive change.
Not everyone agreed. Comedians like Marc Maron, David Cross, and Shane Gillis publicly criticized their peers for performing in what Cross called a “totalitarian fiefdom for…what, a fourth house? A boat? More sneakers?” Gillis, who declined a lucrative offer, said, “You don’t 9/11 your friends.” Pete Davidson, whose father died in the 9/11 attacks, faced backlash for his decision to perform. He admitted on Theo Von’s podcast, “I get the routing, and then I see the number, and I go, ‘I’ll go.’”
For the Saudi government, the festival is part of the broader Vision 2030 agenda, a plan spearheaded by Crown Prince Mohammed bin Salman to diversify the oil-dependent economy and create a more open social environment. Music, once banned in public, now blares from loudspeakers as DJs spin techno remixes. Gender-mixed crowds gather under neon lights, and women in abayas mingle with those in jeans. The religious police, once a fearsome presence, have seen their powers sharply curtailed.
Yet, as Deadline and The New York Times both note, the limits of reform are clear. Political humor was welcomed, but sex jokes landed with a thud. When comedian Cipha Sounds ventured into risqué territory, the audience squirmed. “Oh, sex jokes don’t land in Riyadh,” he quipped. “Got it.”
Kevin Hart, who embraced the opportunity to play a role in Saudi Arabia’s transformation, told the crowd, “But I love what y’all are doing here. I’ll continue being a positive ambassador of your change to the world.” Jim Jefferies, who was later dropped from the lineup after comparing Saudi Arabia’s record to America’s, had earlier argued, “If you don’t agree with how they run their place, isn’t this a step in the right direction?”
Chappelle, ever the provocateur, ended his set with a tongue-in-cheek warning that he feared returning to the United States for what he’d said abroad. He even offered a code phrase to alert fans if he was ever truly silenced: “Here’s the phrase: I stand with Israel.”
The festival’s legacy remains uncertain. For some, it’s a sign of progress—a tentative step toward openness in a rapidly changing society. For others, it’s a troubling example of how money and spectacle can overshadow a nation’s darker realities. But for one night in Riyadh, at least, the world was watching as comedians tested the boundaries of what could—and could not—be said.
