The Puerto Rico joke: comedians on Tony Hinchcliffe, context and pile-ons

October 13, 2026 · 16 min read

The Triggernometry hosts discuss the uproar over Tony Hinchcliffe's joke about Puerto Rico at a Trump rally and comedy taken out of context, the Protect Our Parks comics talk about the pile-on and why roasts matter, Dave Smith ties the episode to the end of cancel culture, and Theo Von and Joe Rogan revisit the Madison Square Garden joke after the election. The episode is a case study in what happens when a roast comic's joke is treated as a political statement.

12 questions on this insight. Answer in your head, then open the card.
What rule does Joe Rogan say he gives every comedian? Show answer

Never do comedy at something that is not a comedy event. A political rally with a run of speakers is, to him, a terrible setup for jokes.

Why does Rogan first blame the booker and not Tony Hinchcliffe? Show answer

He calls Hinchcliffe the world's best roast comic, whose specialty is insult. If you book him he will be himself, so the person who booked him made the mistake.

Where do Rogan and the comics say the Puerto Rico joke came from? Show answer

From Hinchcliffe's obsession with ocean garbage and landfills, and from Puerto Rico's real trash problem, with landfills way over capacity. This is their account of his thinking, not his own.

What comparison does Rogan use for treating a joke as a statement? Show answer

He says it is like watching a Quentin Tarantino movie and saying the man killed that woman, when no one died and everyone is fine.

Which comedians does Rogan say can turn a political crowd into a comedy audience? Show answer

Don Rickles had that with Reagan, and Dave Chappelle would have it because he is a cultural icon. Rogan says Hinchcliffe does not have that.

What did Francis Foster and Konstantin Kisin correct about the room's reaction? Show answer

Having been at the rally, they said it is not quite true that no one laughed. The joke got a bit of a laugh, and he had better jokes that got a bigger response.

What bothered the Protect Our Parks group most? Show answer

Other comedians piling on. They suggest people with grudges waited until Hinchcliffe looked vulnerable, and Rogan says he was distressed over comedians coming after comedians.

Why does Rogan say roasts matter for comedy? Show answer

He says roasts are so funny that they are undeniable to Netflix, pointing to the Tom Brady roast, which he says got Netflix its highest ratings and was completely non-PC.

What is Dave Smith's larger claim about cancellation? Show answer

That it has stopped working and attacks now make people bigger. He credits Elon Musk buying Twitter and the rise of podcasts.

How did Rogan's verdict on Hinchcliffe change after the election? Show answer

Before it he said the mistake was the booker's. Afterward, with Theo Von, he said that at Hinchcliffe's level he should have declined.

What did Rogan later say about whether the campaign vetted the material? Show answer

He said the campaign did not vet it. Someone asked Hinchcliffe to cut one joke, and he replaced it with the Puerto Rico bit.

What limits should a reader keep in mind about these four conversations? Show answer

All are hosted by Rogan, at whose club Hinchcliffe performs, and the guests are fellow comedians or sympathetic podcasters. No one who was offended by the joke speaks.

This is the short form. The full insight has every expert's reasoning, their own words and the sources.