| Politicians, please be mindful of where and when you unleash your favorite insult comic. That's just one of the many practical lessons the political world is learning this week, during the closing days of what people have called the 'podcast election.' On Sunday, comedian-turned-podcaster Tony Hinchcliffe tried to do what he does best – get a crowd fired up with some insulting jokes. The context this time around, however, didn't exactly lend itself to Hinchcliffe's searing style of riling up an audience. In the end, Donald Trump's rally at Madison Square Garden became headline news not for what speakers like Tucker Carlson, Stephen Miller, Hulk Hogan or even Trump said on stage. Instead, it was a bad joke from Hinchcliffe — the punchline of which centered on calling Puerto Rico a garbage island — that became the biggest takeaway of the night. Afterward, the angry blowback ricocheted across social-media platforms. The joke galvanized people in a way that the event's organizers could hardly have imagined, eliciting passionate endorsements of Kamala Harris and widespread condemnations of Hinchcliffe and Trump. Bad Bunny, the biggest Puerto Rican superstar, posted numerous videos of Harris, emphasizing his support. Aubrey Plaza, also of Puerto Rican descent, took to the stage at an event and invoked her "abuelita,"to tell off Hinchcliffe. In response, Marc Maron, a fellow comedian and podcaster, even wrote a lengthy blog post dissecting the state of his profession. "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," he wrote. On the flip side, Jon Stewart played clips of Hinchcliffe making fun of various folks during Netflix's roast of Tom Brady and said he finds Hinchcliffe hilarious. "Obviously, in retrospect, having a roast comedian come to a political rally a week before Election Day and roasting a key voting demographic is probably not the best decision by the campaign politically," Stewart said on The Daily Show. "But to be fair, the guy's really just doing what he does." After Alexandria Ocasio-Cortez and Tim Walz discussed the joke on a Twitch stream, Hinchcliffe responded in a post on X. "These people have no sense of humor," he wrote. "Wild that a vice presidential candidate would take time out of his 'busy schedule' to analyze a joke taken out of context to make it seem racist. I love Puerto Rico and vacation there." Amid the cacophony of denunciations, there was also a fair amount of confusion, as many observers were left wondering, um, Tony...who? Though his name resonates with a certain crowd, he exists in a cultural blind spot for many others. Earlier this year, my colleague Felix Gillette and I traveled to Austin to document the comedy scene that's sprung up around podcaster Joe Rogan. There, Hinchcliffe plays a vital role in the growing ecosystem by providing a high-wire comedy testing ground through which undiscovered talent can measure their skills in front of a raucous live crowd and a panel of proven professionals. Each week, Hinchcliffe records his podcast, Kill Tony, at Rogan's club the Comedy Mothership. The show gives a handful of volunteers, whose names are picked out of a bucket, one minute to perform a stand-up set, after which they're either roasted or praised by Hinchcliffe and his celebrity guests. Of all the comics in Rogan's orbit, Hinchcliffe might be the one who has benefitted the most from the Comedy Mothership's emergence as a powerful new vortex in the comedy industry, and we featured him quite a bit in our resulting story, which you can read here. Along the way, we also spent 40 minutes in the green room of the Comedy Mothership, interviewing Hinchcliffe. In many ways, he told us, his journey to Austin mirrors Rogan's own decampment to the Lone Star State. Ultimately, Hinchcliffe said, it was a reaction to the progressive policies implemented by the California government in response to Covid-19. Hinchcliffe grew up in Youngstown, Ohio and, like a lot of comedians, eventually moved to Los Angeles. When the pandemic hit, the city largely shut down, forcing Hinchcliffe to perform his podcast to an empty room at the Comedy Store. Without its usual live audience, the show fizzled. "It killed us," he said. At one point, Hinchcliffe traveled to Austin to visit Rogan and to play golf with comedian and resident Ron White. Recently, the sport had become something of a mental health release for Hinchcliffe. When he returned to LA, however, he says he learned that people could only golf with members of their household – a problem for Hinchcliffe who lived alone. When the protests surrounding the murder of George Floyd broke out, Hinchcliffe says, he watched as local establishments were set on fire and he saw police cars burning a block away from him. That's enough, he thought. "Why would I want to be in a place that's that vulnerable and susceptible," he said, adding that a situation like that wouldn't happen in Texas because people own guns. So he packed up and followed in Rogan's footsteps, catching a growing cultural wave that was just starting to gain force. "I read the article about Elon Musk moving to Austin while waking up in bed in Austin," Hinchcliffe told us. "I'm like, 'Whoa, I'm right about something for a change.' Like I'm ahead on a stock tip or something like that." Before long, he grew enamored with the state's low taxes and natural beauty. "There's rivers, there's mountains, there's better golf, there's better people," he said. He's now become one of the biggest boosters of Austin's growing comedy scene. On weekends, his comedy buddies tour around the country, performing in arenas and clubs. During the week, they come back, boat around Lake Austin, play golf and perform sets at the Mothership, their new de facto clubhouse. The scene keeps growing. Elon Musk, who also spoke at Trump's MSG rally this past weekend, moved to the city, as did podcaster Lex Fridman. On Kill Tony, politics frequently surface in one way or another. Carlson, the former Fox News pundit, sat in as a guest on the show this year. Another time, fellow comedians Shane Gillis and Adam Ray appeared together performing impressions of Trump and President Joe Biden respectively throughout the show. "It's definitely crazy times," Hinchcliffe said about why comedy has exploded in popularity. "I think people are kind of divided, and they need a release. I think people are working hard to provide for their families. I think the economy's rough, and when the times are rough, people want to get away. They want to laugh." Though maybe not about Puerto Rico, not in the final stages of a divisive political campaign when seemingly the entire nation is on edge. Just days before the New York rally, Rogan had welcomed Trump to Austin for a chummy, meandering, three-hour interview with the former president. It was arguably the biggest sign yet of the sway that Rogan's scene in Texas is starting to exert, not just in the comedy world but also in politics. Naturally, this week Rogan took to his podcast to defend Hinchcliffe. At one point he said the origin of the Puerto Rico joke stemmed from Hinchcliffe's "being environmentally conscious." Rogan said Hinchliffe is "obsessed" with the Great Pacific Garbage Patch and that Puerto Rico's landfills are overcapacity because they're on an island. "From a roaster perspective," Rogan said, "that's where the joke comes from."
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