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.

The insight in about three minutes.

In four conversations on The Joe Rogan Experience, before and after the 2024 election, comedians and podcasters reach much the same reading of Tony Hinchcliffe's Puerto Rico joke: it was a roast comic's joke, and the mistake was the room. Joe Rogan's rule is one he says he gives every comic: "I tell all comedians don't ever do comedy at something that's not a comedy event." A daytime political rally eight days before an election, in front of a crowd that did not know the comic, was the worst case of it.

Talking with Francis Foster and Konstantin Kisin a little over a week before the election, Rogan does not put it on the comic. He calls Hinchcliffe the world's best roast comic, so the person who booked him made the mistake. He says the joke kills at comedy clubs, that he does not like it, and that he would have told Hinchcliffe not to do it. He explains that it came from Hinchcliffe's obsession with garbage and from Puerto Rico's landfills being way over capacity. Treating the line as a claim, he says, is like watching a Quentin Tarantino movie and saying the man killed that woman. And only a few comedians, a Don Rickles or a Dave Chappelle, can turn a political crowd into a comedy audience just by walking on.

Nobody is surprised that the line was used as campaign ammunition. In that first conversation it is said of the other side: "I'd use it too." The Protect Our Parks group with Shane Gillis, Mark Normand and Ari Shaffir agrees that people trying to win will exploit every last thing. What bothers that group is other comedians piling on, which they put down to grudges and to fear of the internet. Rogan says he was distressed by comedians coming after comedians, and argues that roasts will help save comedy, pointing to the Tom Brady roast on Netflix.

Dave Smith, the day after the election, calls the outrage a political tool and makes a larger claim: cancellation has stopped working, and attacks now make people bigger. He credits Elon Musk buying Twitter and the rise of podcasts. The group notes that the backlash seemed to make Hinchcliffe bigger too.

They do not agree on everything. Before the election Rogan blames the booker; a few days after it, with Theo Von, he says that at Hinchcliffe's level he should have declined. The first conversation passes along that the material had been gone over; later Rogan says the campaign did not vet it, and that the Puerto Rico bit replaced a joke someone asked him to cut. Whether the joke is any good is the least settled point. Smith treats the failed cancellation as a trend, while Rogan says news outlets had stories ready to blame Hinchcliffe if Trump lost.

Keep in mind who is talking. These are all friends and defenders of the comic, no one who was offended by the joke speaks, and the comedians who criticized him are described, not heard.

What to do with it: if you perform, keep comedy to comedy events, know your standing with the room, and decline when the setup is wrong. If you book, match the performer to the event. Before reacting to a clip, ask where it was said and for whom, and separate a joke from a claim. If your objection is to the company someone keeps, say that. Do not weigh in while the pressure is at its height. And if it happens to you, laugh at yourself and use it.

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