It was the “joke” heard around the world, one that some are speculating – a little too optimistically, perhaps – might help swing the US election. Last Sunday, US insult comic Tony Hinchcliffe described Puerto Rico as “a floating island of garbage” while standing at a podium emblazoned with “Trump Vance 2024”, in New York’s Madison Square Garden. It prompted a huge backlash among Puerto Ricans, including some very famous members of the community, as well as that rarest of things: contrition from the usually unapologetic Trump campaign, which said that Hinchcliffe’s comments did not reflect the (famously moderate) views of Donald Trump himself.
I should stop here to apologise to anyone who has come to The Guide for a break from the oxygen-hogging, 24/7 carnival that is the US election. Normal service will resume next week, I promise – but this is a political story that is, at its very least, culture-adjacent. And it prompts an interesting question: how did Hinchcliffe, a shock comic whose routines would make even the crowd at Late ‘n’ Live retreat to their fainting couches, end up as the opening act at a major political rally? The answer has a lot to do with the growing bromance between insult comedy and the right wing.
If you hadn’t heard of Hinchcliffe before the Puerto Rico palaver, that’s probably understandable: he’s rarely interacted with the comedy mainstream, bar an appearance on Netflix’s hugely popular Roast of Tom Brady earlier this year. Which isn’t to say that he isn’t hugely popular: his standup showcase/roast battle Kill Tony is one of the highest-ranked comedy podcasts on the planet, regularly vying with The Joe Rogan Experience at the top of the podcast charts. (Rogan and Hinchcliffe are close: Rogan coaxed Hinchcliffe into moving to Rogan’s home base of Austin, Texas; Kill Tony is recorded at Rogan’s Comedy Mothership venue in Austin; and the two often appear on each other’s podcasts.) A month before Trump descended on Madison Square Garden, Kill Tony casually bested him by selling out two dates at the arena.
In a sense, it’s not hard to see why Kill Tony is so well liked. The premise – budding standups are savagely critiqued by a panel of professional comics in front of a studio audience – is a juicy one, updating the comedy roasts of Dean Martin and Don Rickles for a more clippable, social media-friendly age. And it manages to lure in some big names in the comedy world – Rogan, Shane Gillis, Whitney Cummings (though Hinchcliffe also has an unpleasant habit of coaxing prominent far-right non-comedians, including Tucker Carlson, Jordan Peterson and Alex Jones, on to the show).
As for the humour … well, roast comedy inevitably has risks attached, and Kill Tony can sometimes be pretty repellent, notably in a now-notorious 2021 show where Hinchcliffe launched a racist tirade at a Chinese-American comic.
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Fans would argue that suffering such moments is the trade-off for the freedom that the comedy roast offers. And, in fairness, a good comedy roast with talented standups dancing along the line of offence is pretty electrifying. There’s a strange equality at play: the victim of a joke gets a chance to enact revenge at some point in the night. Everyone present operates under a single shared comic belief: that all that matters is whether something is funny or not.
Things have become more complicated in that regard lately, though. That mantra of saying the unsayable has been latched on to by a movement of standups who blur the lines between free speech comedy activism and something more avowedly rightwing.
Veteran comic and podcaster Marc Maron wrote in response to Hinchcliffe’s rally appearance: “The anti-woke flank of the new fascism is being driven almost exclusively by comics. When comedians with podcasts have shameless, self-proclaimed white supremacists and fascists on their show to joke around like they are just entertainers or even just politicians, all it does is humanize and normalize fascism.”
That last point was a veiled dig at comics like Theo Von and Andrew Schulz, who have invited Trump on to their podcasts for cosy chats, as part of the Trump campaign’s attempts to court young, disengaged male voters.
By appearing at Trump’s Madison Square Garden event, Hinchcliffe took this alliance to its absurdist endpoint. But in doing, so he fatally misunderstood the brief. A political rally is a dramatically different arena from a comedy club, where you can hide behind the idea of “anything goes”. What’s more, performing at this sort of political rally is a betrayal of the entire ethos of roast comedy: it lacks the willing victim, who has the opportunity to clap back, meaning that Hinchcliffe was left saying objectionable things to an audience who had no chance of rebuttal.
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Which, of course, makes him no different to much of the rally’s other speakers – including Trump himself. It has long been said (perhaps best in this Emily Nussbaum New Yorker piece (£) from way back in 2017) that Trump operates like a standup comedian – in form and rhythm, if not in quality of material. He is a man well accustomed to the comedy roast, and has played both victim and perpetrator (though sometimes he has shown an extremely thin skin). And he has learned, over his decade-long (and it has felt so long) political career, the value of shock comedy, of being able to say something outrageous and then walk it back by saying “I was just kidding … what’s the matter, can’t you take a joke?” It’s been a crucial component of his Teflon-like political status.
Wouldn’t it be a delicious irony, then, if another roast comedian helped the comedy roast president lose the election next week?
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