Cancelled Comedy Goes to Riyadh...

Simon Lincoln Reader

September 11, 2025

7 min read

Saudi Arabia is about to welcome Tim Dillon, Dave Chappelle, Tom Segura and others for a two-week comedy festival that would likely spark protests in Europe. The gathering highlights both the Kingdom’s growing confidence and the irony of Riyadh becoming a haven for expression while liberal democracies tighten their own speech boundaries.
Cancelled Comedy Goes to Riyadh...
Image by Zhe Ji - Getty Images

There’s going to be a funny thing happening in the world at the end of this month. Some of America’s best comedians are gathering in one place for two weeks; if you’re lucky enough to be in that one place, you’ll have the chance to watch the often explicit and politically incorrect routines of Tim Dillon, Bobby Lee, Andrew Santino, Dave Chappelle, Jessica Kirsehn, Tom Segura and others.

The comedians have been issued free license, unchained basically, something which would frighten the pants off the UK’s Liberal Democrats and the Green Party, which are now basically the same thing. Some, especially Dillon and Lee, can offend at levels previously unimagined; were this to happen in the UK, the flying squad would invariably interrupt the shows, or activists would pressure the venue to cancellation.

So if it’s not in the UK or the EU, who would host such a thing, you ask? Who would be mad enough, in this febrile age, to invite so many lightning rods into the same place at the same time? Riyadh, Saudi Arabia, it turns out…

Riyadh’s unlikely reinvention

No bait. Riyadh is now a home to comedy in the same way Buenos Aires is a home to sensible fiscal policy. Similarly, Milan was never a domicile for the rich in the way Monaco was; with a bit of initiative, Giorgia Meloni turned it into such and subsequently poached wealthy Londoners exhausted by goblin politics, tax and crime. But of all the transitions, Riyadh, as a new destination for unfiltered comedy, is the most remarkable.

From Khashoggi to global stage

We’re approaching the seventh anniversary of the murder of the Saudi journalist Jamal Khashoggi in Turkey, an event that was supposed to have banished Crown Prince Mohammed bin-Salman (MBS), ultimately the guilty party, into a Gaddafi-like existence. The brutality of Khashoggi’s end was reminiscent of Bashar Al-Assad’s father Hafez machine-gunning his “friends” in the dunes outside Damascus, so the west was primed to isolate yet another medieval caricature before trumpeting its virtues and standards across the region’s peninsulas and deserts.

That didn’t happen. Instead, Saudi Arabia, and MBS, assumed an astonishing recovery. Central to it was ambition; whilst western interests claimed to look away from what they described as a backward, despotic regime, they couldn’t but admire the sheer balls of MBS as he spelled out a future for his people that European liberals were incapable of delivering for theirs. MBS coupled this strategy with reforms, and by the time the geniuses at the New York Times and Bloomberg sat down to write books about how beastly he was, the shift had already occurred: MBS had not only barged back on the world stage, but arguably wielded more power than ever before.

A city wrenched awake

For all his ways, MBS is clearly a phenomenal operator, taking his capital by its neck and jerking it into activity. Within five years of seizing power he completed the King Abdullah Financial District adjoining the city that had been subjected to the same pedestrian approach to development that curses the UK’s planners. He has been jeered for supposedly over-promising on Neom, the linear giga city he hopes will house nine million souls in the desert, but I would caution critics.

Many residents of Johannesburg I suspect privately long for someone with his methods to grab the city’s water crisis by the throat. Perhaps some would wish him to deal with the lazy, greedy, shameless administrators who are clearly unwilling or incapable to address the problem. That would be something.

The Tim Dillon factor

It is difficult to measure the intelligence of your average comedian. In London and Cape Town, the comics are generally awful, spiking their routines with social justice themes that prompt applause from their audiences. Applause in comedy is the equivalent of devil worship. The First Rule: impulse only. Personally, I find the sequence of an Asian tourist unwittingly alighting from his vehicle in the Kruger National Park to take close-up shots of mating lions on the roadside funnier than I do Chester Missing.

But there is no difficulty when it comes to Tim Dillon. He is wildly smart. A former cocaine and vodka martini addict, Dillon was obese from a young age, then locked in a boiler room selling mortgage -backed securities just as the trend blew up in the 2008 global financial crisis. Drying out, he thought about a career in comedy, and prepped for it by taking a job as a tour bus guide in New York.

I’ve seen Dillon twice, and got to know his former producer Ben Avery a bit (Avery since left to establish his own podcast, Lemon Party, I strongly advise against looking up what that means). Dillon is formidable holding court as a headline act, boisterous, menacing, cynical, self-deprecating, sometimes even a bit nervous. These qualities in a comedian speak to ups and downs, passages of near depression and lowliness, interrupted by manic euphoria.
But it’s underwritten by supreme reception of emotion. Audiences laugh at Dillon’s shows. They laugh so hard they fall out their chairs. They cringe and cry. They don’t clap.

The Kingdom’s cultural gamble

Clearly nobody told our new management classes, the right-on media commentators, tax enthusiasts, broadcast regulators and creative industry bosses, that the old world will always seize a self-imposed crisis to fashion into their own opportunity. So you have to hand it to The Kingdom, very much the old world. They have watched as modern western culture has knotted itself stupid. They have stood back as we’ve attacked each other, sued each other, grassed on each other to the police, mostly for having apparently inferior or not suitably progressive views. They saw this in Hollywood’s shape-shifting to diversity casting and its net result: poor content crafted with apparently one intent, to prevent yet another identity protest outside. They’ve seen the censorship, the terminal decay of political movements founded on expression and rights, the erection of state monitoring bodies that resemble their own notorious religious police. They’ve found a way to make it work out for them.

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