Donald Trump Got the Tony Hinchcliffe He Hired

Photo: Evan Vucci/AP

In the context of a roast, there tends to be a shared understanding among the guest of honor, the panelists on the dais, and, crucially, the audience that nothing is off-limits. It’s why comedian Tony Hinchcliffe’s joke during Netflix’s The Roast of Tom Brady earlier this year that Kevin Hart is “so small that when his ancestors picked cotton, they called it deadlifting” didn’t cause a gigantic hullabaloo. In May, when the streamer aired the event live, Hinchcliffe’s set was the most mainstream exposure he’d received yet. That was until this past weekend, when Hinchcliffe spoke at a political rally for Donald Trump at Madison Square Garden and sparked controversy by telling roast jokes in a wildly different context. “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,” he said in one joke that sparked viral outrage and celebrity backlash. Another saw him propose that Palestinians and Israelis settle their ongoing conflict with a game of rock, paper, scissors: “You know the Palestinians are going to throw rock every time. But you also know the Jews have a hard time throwing that paper.”

That Hinchcliffe would use this platform to tell jokes of this nature would have been unsurprising to anyone familiar with his work. He is, first and foremost, a roast comic who revels in shock — the type of performer who inspires YouTube compilations with titles like “Tony Hinchcliffe Being a Savage for 10 Minutes Straight.” It’s a sensibility he developed as a means to capture audience attention at the Comedy Store in Los Angeles, where he honed his chops. “My style is very much arranged around the darkness and extremely late spots and having to be compelling,” he said in a 2017 interview. “I had no choice. Normally by the time I go onstage, they’ve already seen 14 of the best comedians in town.”

Working in that setting, Hinchcliffe caught the attention of Joe Rogan and Jeff Ross, who separately tapped the comic to open for them on the road, and whose audiences also rewarded Hinchcliffe’s inclination toward hot-button subject matter and prickly jokes. Through Ross, Hinchcliffe eventually found his way into the writers’ rooms of several Comedy Central roasts, where he found a natural outlet for his comedic skill set. Hinchcliffe has also released two stand-up specials: 2016’s One Shot, which premiered on Netflix but is no longer available to stream online; and 2020’s Making Friends on YouTube. In each, he barrels through charged topics one by one — like transgender women in sports and Bill Cosby’s legacy — to make wordplay-heavy jokes about the supposed hypocrisies of moralists, then to subsequently assert that he’s breaking an iron taboo by doing so. The latter special, for example, opens with a joke about abortion being banned in Alabama, which he calls “a state in which abortion should be mandatory.” He notes that Alabama is the birthplace of Helen Keller, the extremely overused comedy-reference point. Then, despite no discernible audience pushback, he adds, “Those of you groaning on this side of the room, let me remind you Helen Keller is dead. Even if she was alive and in this showroom, she would have no idea what I just said.”

It’s a style that has landed him in trouble before. In 2021, Hinchcliffe caused a stir when, during a stand-up performance at Vulcan Gas Company in Austin, Texas, he referred to comedian Peng Dang, who preceded him on the evening’s lineup, as a “filthy little fucking chink” and mocked him using an exaggerated Chinese accent. Hinchcliffe was dropped by his agent at WME in the aftermath but has no regrets about how the incident unfolded. “It was a joke, and my stance is that comedians should never apologize for a joke,” he said in a 2024 interview. “Real comedy fans see through it. They want that line. They know that line. And they love that line. That line is exactly where I love to exist, and I push that to the limits.” Per comments on the dedicated sub-Reddit for his massive podcast Kill Tony, even Hinchcliffe’s fans are divided on whether his stand-up is too derivative or reliant on contrived provocation.

More so than for his stand-up or writing accomplishments, that podcast — launched in 2013 with co-host Brian Redban (previously best known as the producer of The Joe Rogan Experience) — is the source of Hinchcliffe’s popularity. Taped at Rogan’s Comedy Mothership in Austin since 2020 (though it occasionally tapes elsewhere on the road), it is the 13th most-listened-to podcast on Apple’s comedy-podcast chart, and the show’s episodes routinely rack up more than 3 million views on YouTube. Recorded live in front of an audience, the podcast is a quasi–open mic, where comedians’ names are drawn from a bucket, then they are given one minute to perform stand-up, which is then critiqued by a panel of comedians. Panelists often include the usual suspects, like Rogan, Shane Gillis, Tim Dillon, Andrew Schulz, etc. — all of whom have huge podcast followings and reputations for generating offense — but also acclaimed comedians outside that circle including Sam Jay, Eddie Pepitone, and Punkie Johnson.

In rare instances, these comics’ feedback takes the form of constructive tips on joke structure or performance style, but it more often devolves into no-holds-barred roasts of the comedian hopefuls. Those who come out on top are usually those who demonstrate the same lack of regard for cultural sensitivities that Hinchcliffe and his fellow panelists do. It’s ultimately what the live audience who attends the show’s tapings come to see, and it’s what the rabid, overwhelmingly young male fan base tunes in to the show on YouTube to get a fix of. To that end, an entire Kill Tony ecosystem has sprung up to serve this market. The show has become a career launching pad, with comedians like David Lucas, Hans Kim, Kam Patterson, and Jeremiah Watkins establishing lucrative touring careers thanks to repeat appearances on the show; on August 9 and August 10, Hinchcliffe hosted live, sold-out Kill Tony recordings at Madison Square Garden.

Trump has been courting young male podcast listeners aggressively in recent weeks, with appearances on The Joe Rogan Experience, Andrew Schulz’s Flagrant With Akaash Singh, This Past Weekend w/ Theo Von, and more. Most of these comedians are political agnostics; they’re too interested in maintaining their image as nonpartisan freethinkers to explicitly support one presidential candidate over another at a rally, but Hinchcliffe has long been a public proponent of Trump. (He was performing pro-Trump material onstage as far back as 2017.) Yet Hinchcliffe’s comedy style was never going to fly in this setting when broadcast to the public. A presidential rally is not a Kill Tony open mic, where comedians without the power to enact policy are given leeway to find out where the lines are in service of comedy. It’s why Hinchcliffe’s attempt to defend himself from criticism — by writing on X that his critics “have no sense of humor” — doesn’t land. Even if Hinchcliffe’s message at the rally was no more racist than Trump’s own throughout the campaign, given all his fearmongering about “migrants,” the tone was all wrong. The goal of a good roast joke is to establish a clear target and hit it as accurately as possible. The goal of political messaging is to gesture at big ideas and talk in circles around them. If a dog whistle gets laughs, it means too many people understood it.

In the backlash that followed Hinchcliffe’s remarks, Danielle Alvarez, a senior adviser with the Trump campaign, released a statement distancing the former president from Hinchcliffe’s Puerto Rico joke. “This joke does not reflect the views of President Trump or the campaign,” she said. But for all the walking back the campaign is doing now and all the fuss that specific joke has caused, Hinchcliffe’s set in its entirety appeared to play fine in the room. “Republicans are the party with a good sense of humor,” Hinchcliffe said at one point during his address. “Free speech is under attack.” Then, like clockwork, a bunch of Democrats got mad. The legitimacy of the grievance is, unfortunately, irrelevant. If the Trump campaign booked Hinchcliffe to convey to his audience that a vote for them is a vote to protect the uninhibited comedy they’d see at a Kill Tony show, they may just have gotten that message across.