As the first-ever Riyadh Comedy Festival drew to a close last week, a debate raged across entertainment as to whether the free speech warriors who’ve decried cancel culture in their stand-up gigs — from Dave Chappelle to Bill Burr — were being rank hypocrites by renting their comedy talent to a repressive Islamic regime.
“How can any of us take any of you seriously ever again?” comedian David Cross wrote in an open letter last week that tore into the participating comedians. “All of your bitching about ‘cancel culture’ and ‘freedom of speech’ and all that s–t? Done. You don’t get to talk about it ever again.”
Saudi Arabia has taken big steps to open its conservative Muslim culture and Arab traditions to Western influence in the past few years. It allowed women to drive, make some decisions without a male guardian, participate in the workforce and play in sports, all while building out a massive entertainment ecosystem, which included this new festival.
But should American comedians participate? Should any American artist who believes in freedom of expression?
Get over it. We’re taking the money. How about that?”
– Tim Dillon, comedian
The question will become increasingly relevant in a shifting moral landscape where Saudi Arabia is prepared to pay handsomely for visiting Hollywood talent, and as the battle over free expression in the United States takes on ominous overtones with the Trump administration threatening comedians from Jimmy Kimmel to Rosie O’Donnell and Stephen Colbert.
“Their reputation is going to depend on whether people see them as fearless or independent or honest people who say the things the rest of society can’t,” said Michael Halcomb, a professor and faith-based stand-up comedian, who described the dilemma as comedians trying to manage their public “face.” “When they go and perform in Saudi Arabia, some people see that as compromising their face, like they’re trading their integrity for money or for political gain or access, but the comedians might frame it differently.”
“Every comedian has to evaluate it for or against their own brand and the values that their brands represent,” said Eric Schiffer, the chairman of crisis PR firm Reputation Management Consultants. “Most fans will not, at the end of the day, care, nor remember in six to nine months whether their favorite comedian may have performed in Saudi Arabia, and many won’t even find it relevant.”

Indeed, while the controversy has bubbled up over the last two weeks, it’s almost certain that some other outrage will take its place in the near future. For big name comedians like Kevin Hart, Jimmy Carr and Aziz Ansari, who all attended, Schiffer said any outrage could be mitigated down the line.
“That’s easily reframed through future work and other appearances, and even at some point talking about it as part of your comedy routine,” he added.
The Riyadh Comedy Festival’s conclusion on Thursday capped a two-week-long discourse that roped in comedians across the political spectrum, with some comics defending their participation by claiming, perhaps jokingly, the U.S. didn’t fare much better when it came to free speech.
It didn’t work. Scores of people, including top comedians, tore into the 36 comedians who participated in the event, with the likes of Marc Maron and Gianmarco Soresi alleging the performers traded in their ethical values in favor of serving as tools, in Soresi’s words, “Saudi propaganda.”
“It’s embarrassing to go on stage and tell jokes that if some of the audience members tweeted from their own personal accounts, could lead to them being executed,” Soresi told CNN last month.
The response from the festival performers has been, to put it mildly, mixed.
Ansari told Kimmel last week that he felt his participation could help the country “be more open and to push a dialogue” rather than imposing a policy of isolation. He said he would donate a portion of his fee to human rights groups such as Human Rights Watch, but the group said Thursday that it would refuse his donation.
Others, such as Burr, remained defiant and rebuked critics who felt their engagement was misguided.

“All of these sanctimonious c–ts out there…who don’t really sincerely give a s–t,” Burr told Conan O’Brien last week. “If you actually give a f–k about those people and how they’re living over there, there’s gonna have to be these types of things to pull them in.
“I will tell you, the Cheesecake Factory in Riyadh, it’s incredible,” he added. “It’s right next to Pizza Hut and KFC, and if you want a pair of Timberlands, it’s across the street next to the Marriott, catty-corner to the f–king Hilton.”
Such an image of a brand-fueled world is one that the Arab nation has tried to project as part of its country’s Vision 2030 — backed by its Public Investment Fund, which is estimated to have roughly $1 trillion USD in its coffers — to diversify the country’s economy and develop its entertainment sectors, thereby rebranding its image on the international stage. It founded the General Entertainment Authority in 2016, one of two cultural agencies aimed at supporting the quest, and the country invested $64 billion in its entertainment sector in 2021.
Yet, despite its public vows to loosen restrictions in recent years, its vicious punishment of critics persists. U.S. intelligence concluded that Crown Prince Mohammed bin Salman ordered the brutal murder of U.S.-based journalist Jamal Khashoggi at a Saudi consulate in Turkey in 2018. Even international condemnation over the killing has not halted its tactics, as the regime executed journalist Turki al-Jasser in June after a seven-year detention for “high treason” after operating an anonymous Twitter account that criticized Saudi officials.
Women still require a male guardian’s permission for important life decisions, including marriage, and same-sex activity, regardless of gender, is still punishable by death.
These issues highlight the split nature of the Saudi dilemma, which is embracing aspects of Western culture and relying on the likes of Western music artists for the country’s Soundstorm Festival (this year’s lineup features the queer pop singer Halsey and Grammy winner Post Malone, among others).
Hollywood types, too, have not seemed bothered by such issues of authoritarian tendencies, including the stifling of speech, the murder of Khashoggi and accusations in U.S. courts over the country’s involvement in the Sept. 11 terrorist attacks (which the Saudis have denied).

Last year, the country hosted its fourth annual Red Sea International Film Festival, a cinema showcase in Jeddah founded by Prince Bader bin Abdullah bin Mohammed bin Farhan Al-Saud, the country’s minister of culture. It brought Hollywood starpower, with the likes of “Wicked” star Cynthia Erivo, “Sex and the City” lead Sarah Jessica Parker and Oscar-winning filmmaker Spike Lee gracing its theaters and red carpet.
Hollywood’s eagerness to show up for Saudi Arabia represents a significant shift. In 2019, Hollywood power broker Ari Emanuel returned a $400 million investment from Saudi Arabia into the talent agency Endeavor — only to partner with the country this year through its sports company TKO to promote Zuffa Boxing, which also struck a streaming deal with Paramount. Other notable plays on sports include the Saudi-backed LIV Golf tour and the launch of the Saudi Arabian Grand Prix Formula 1 event in 2021.
One top talent agent told TheWrap the country would likely invite more American icons.
“They pay too well and Hollywood has short attention spans,” the agent said. “There is very little money left in this business now, so stars will go where they’re paid.”
Comedians who participated in the Riyadh festival were required to refrain from criticizing the regime — specifically not to “degrade, defame, or bring into public disrepute, contempt, scandal, embarrassment or ridicule” — according to a copy of a contract that one comedian refused to sign and published online. Comedian Tim Dillon, who was scheduled to participate before getting excised from the lineup for criticizing the government, said on his podcast in August that he was offered $375,000 to perform. Others, he claimed, were offered up to $1.6 million.

“They’re paying millions of dollars to comedians,” Dillon said at the time. “Get over it. We’re taking the money. How about that?”
But this moment especially follows the U.S.’ own intimidation of comics critical of the government, with Stephen Colbert and Jimmy Kimmel the high profile targets of the Trump administration.
While both comedians remain on the air, the actions of large conglomerates in the face of government intimidation led some comedians to warn that the U.S. risked a turn toward authoritarianism.
It presents a problem for participating comedians like Chappelle or Louis C.K. and Ansari, who have derided cancel culture in the United States: Speak out in defense of U.S. comedians who appear to be silenced in the face of government intimidation, like Kimmel or Colbert, or accept hordes of money from a nation that’s been repeatedly rebuked by human rights groups for stifling speech and killing of a U.S.-based journalist?
The answer, for some, appears to be… maybe?
“There’s people over there that don’t agree with the stuff that the government’s doing, and to ascribe the worst behavior of the government onto those people, that’s not fair,” Ansari told Kimmel on Wednesday. “Just like there’s people in America that don’t agree with the things the government is doing.”
Others, however, were more blunt.
“I just know I get the routing, and then I see the number, and I go, ‘I’ll go,’” comedian Pete Davidson told podcaster Theo Von last month.