Tony Hinchcliffe Managed to Bomb Telling Racist Jokes at a Trump Rally, Which Is an Achievement

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The internet was abuzz this week after Donald Trump hosted a rally in Manhattan at Madison Square Garden. As usual, it featured plenty of washed bozos (Hulk Hogan! Rudy Giuliani!) simping for their candidate and figuratively reenacting this classic Dril tweet. But one of Trump’s new friends, comedian Tony Hinchcliffe, said the quiet part so loudly that even the Trump campaign had to distance itself. His speech featured a string of blatantly racist jokes, the headline grabber being, “I don’t know if you guys know this, but there’s literally a floating island of garbage in the middle of the ocean right now. I think it’s called Puerto Rico”—which, on top of what’s plainly offensive about it, just isn’t at all funny. It barely got a laugh, which is impressive—Hinchcliffe told a joke so foul that even a packed-out Garden full of Donald Trump voters thought it was over the line. But it did manage to overshadow another unfunny zinger, about Travis Kelce potentially being “the next O.J. Simpson.” That’s right: Hinchcliffe did a bit about imagining the violent death of Taylor Swift, and yet Swifties aren’t the group that’s maddest at him today. That’s how you know the Puerto Rico joke was bad.

Hinchcliffe is very, very popular and known for his roasting skills. (One of the stranger parts of this story is dusty liberal satirist Jon Stewart using The Daily Show to come to Hinchcliffe’s defense, arguing that Hinchcliffe was “just doing what he does,” as if there wasn’t a huge and obvious difference between implying that 3.2 million American citizens live in filth and razzing your fellow comedians from the dais while roasting Snoop Dogg or Tom Brady. Hinchcliffe has written for and appeared on eight Comedy Central Roast episodes, all told. But he’s most famous for hosting the Kill Tony podcast since 2013. The podcast features both professional and amateur comedians performing for a panel of judges for 60 seconds and then enduring their criticisms. Over the summer they did a sold-out live version at the scene of the crime, Madison Square Garden. (Of course, he got his start opening for Joe Rogan.)

I thought a comedian’s job was to make people laugh, but priorities seem to have significantly shifted. Now it’s about pandering to whichever side will buy your tickets and stream your specials. The most popular comedians are no longer trying to be funny; instead, they’re trying to be clever, provocative, and political. Look at Dave Chappelle. Someone who has made almost all of us belly laugh is now doing 20-minute chunks of strange anti-trans material in front of sold-out audiences. Chris Rock can only talk about getting slapped, and Joe Rogan (who I have unfortunately seen do stand-up at the Fox Theatre in Atlanta) is one of the least funny people on earth. Tim Dillion, who is naturally very funny, would rather chat with RFK Jr. and JD Vance than recall another hilarious meal at a corporate steakhouse or flight on a private plane.

Comedy was ruined by podcasting. Every guy who had ever waited two hours at “The Store” only to get bumped in favor of a George Lopez drop-in instead got a microphone and producer and mostly stopped telling jokes. Some comedians did use the medium creatively, experimenting and pushing boundaries. But plenty of others just started talking for hours and hours—and since podcasts didn’t offer the same real-time feedback they were used to getting onstage, they began obsessing over social media, and the perceived existential threat to their livelihood posed by so-called cancel culture. Now it’s all politics and no laughs.

As a wildly popular professional comedian, you can say whatever you want and support the political candidates of your choosing. I am not the free-speech police—but this job used to be about being funny, and now it seems to be mostly about ruffling feathers and drawing hard lines in the sand.