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 apologize 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.
The Rise of Kill Tony
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).
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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