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Watch: Tony Hinchcliffe jokes that are far more offensive than Puerto Rican one

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Comedian Tony Hinchcliffe , known for his sharp wit and often polarising humour, has long drawn attention—and controversy—for his edgy jokes that push boundaries. Recently, his commentary has provoked particular ire among Democrats, especially following his apparent alignment with Trump’s campaign rhetoric. His joke about Puerto Rico has the Trump campaign on the backfoot.

Tony Hinchcliffe: Comedian without a filter

After relocating to Los Angeles in 2007, Hinchcliffe began performing as an opening act for stand-up comedians such as Joe Rogan and Jeff Ross, whom he described as a mentor. He also contributed as a writer for the Comedy Central roasts of James Franco , Justin Bieber , Rob Lowe, and Bruce Willis. In May, he joined comedians like Kevin Hart and Nikki Glaser to roast Tom Brady on Netflix, which had also hosted his 2016 stand-up special, One Shot.

Since 2013, Hinchcliffe and Brian Redban have co-hosted the popular Kill Tony podcast, which boasts nearly two million subscribers on YouTube. The weekly live show is filmed outside of Rogan’s comedy club in Austin, Texas. In recent years, Hinchcliffe’s material appears to have taken on a more political tone. Back in 2017, he, who had been nicknamed "The King Joffrey of Comedy," mentioned to Metro that, while he wasn’t specifically pro-Trump, some of his material was, as he tended to focus on positives.

This wasn’t the comic’s first encounter with controversy. In 2021, after being introduced at a gig in Austin, Texas, by fellow comedian Peng Dang, Hinchcliffe used a racial slur while speaking about Dang on stage. The remarks were recorded and widely shared on social media, leading to Hinchcliffe’s dismissal by his talent agency, WME, along with the cancellation of several scheduled performances.

Currently represented by United Talent Agency, Hinchcliffe has never issued an apology for the incident. In October 2023, during an appearance on the YouTube show TRIGGERnometry, he accused Dang of being "a Chinese spy" and suggested the backlash was part of “an orchestrated attack by the Chinese media.”

In response, Dang remarked to Variety earlier this year that it seemed unlikely any nation would dispatch a spy to be a stand-up comedian, noting that spies typically sought classified information on science, technology, or government affairs, rather than comedy. He added that, at the time, there had been a notable rise in anti-Asian sentiment, supported by statistics, and that he personally knew individuals who had been injured in Texas.

In the same article, Hinchcliffe reinforced his stance, saying he believed he hadn’t done anything wrong and found the situation bewildering, particularly given that it was a former opener who shared the video. He told Variety in April that, in his view, comedians should never apologise for jokes, nor halt their work under criticism, and that any such incidents should be used as further material for their performances.

Here’s a look at some of Hinchcliffe’s most offensive jokes that makes his Puerto Rico joke look tame:




Walking the Line: The Nature of Offensive Jokes

Hinchcliffe’s humour has always been abrasive, designed to push audiences out of their comfort zones, an approach that aligns him with the classic stand-up tradition of using comedy as a means to challenge societal norms. However, his alignment with the Trump campaign’s ideology has given his jokes a new edge, offending not only Democrats but many viewers across the political spectrum. His remarks often revolve around issues such as immigration, political correctness, and social justice—hot-button topics that, when handled with his cutting style, tend to alienate audiences who feel personally attacked by his words. For those aligned with progressive views, Hinchcliffe’s humour is less about satire and more about reinforcing divisive narratives.
In recent years, offensive jokes have come under scrutiny, with an increasing number of comedians finding themselves targeted for remarks once deemed innocuous or “just a joke.” Social media plays a significant role here, amplifying reactions and enabling backlash to go viral within hours. Public perception of humour has evolved, and while comedians traditionally claimed the license to “say the unsayable,” today’s cultural landscape has made audiences less tolerant of humour that feels out of step with social justice and inclusivity ideals.

Tony Hinchcliffe and Trump: A Risky Alliance

Hinchcliffe’s recent alignment with Trump campaign views has sparked significant backlash. For a segment of the population, Trump’s name alone is polarising; aligning with his ideology is, for many, a line-crossing act. Hinchcliffe’s apparent sympathy with certain Trump views has been perceived by critics as an endorsement of values they believe promote divisiveness, and his jokes reflect this alignment, especially when they poke at Democratic policies or public figures.
This relationship with Trump has intensified reactions to Hinchcliffe’s work, with some arguing that he is no longer delivering jokes for humour’s sake but rather using his platform to propagate a political stance. By stepping into the realm of partisan politics, Hinchcliffe may have inadvertently altered his career trajectory. While his fanbase may see him as a truth-teller exposing the absurdity of progressive “wokeness,” others see him as crossing into dangerous territory, using comedy to validate controversial and, in some eyes, harmful viewpoints.

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The Broader Context of Offensive Comedy in a Politically Charged Era

Hinchcliffe’s situation speaks to a broader trend within comedy, where the genre’s role has transformed from purely entertainment to a form of political commentary. As comedians have increasingly become cultural commentators, they face pressure to navigate public sensitivities around race, gender, and political ideology. The fallout from Hinchcliffe’s comedy aligns with this trend, with audiences expecting not only humour but a kind of ethical accountability that was largely absent in previous eras of stand-up.
The comedian’s role, historically, has been to expose society’s hypocrisies, often by using “punching down” or “punching up” techniques to direct humour at those in power or societal expectations. In Hinchcliffe’s case, however, his critics argue that his jokes too often punch down, particularly when aligned with Trump’s divisive rhetoric. This has led some to question whether comedians like Hinchcliffe are hiding behind the “it’s just a joke” defence to avoid accountability for spreading harmful messages.

A Divided Audience: Support and Condemnation

While critics argue that Hinchcliffe’s humour crosses lines, his supporters maintain that he is simply exercising his freedom of speech in a genre where pushing boundaries is not only expected but necessary. His defenders argue that the backlash is less about the content of his jokes and more about his willingness to challenge progressive ideologies openly. In this view, Hinchcliffe’s work serves as a reminder that comedy should remain a space where “sacred cows” can be questioned without fear of censorship.
The controversy over Hinchcliffe’s recent Trump-related jokes also speaks to the intense partisanship of the current political climate. Comedy, once a unifying medium, is now divided along ideological lines, with audiences gravitating towards comedians who align with their political beliefs. This trend creates an environment where comedians like Hinchcliffe find a ready-made audience that celebrates jokes others might find offensive or dangerous. However, this alignment risks narrowing his audience to only those who share his political views, making it challenging for him to attract a diverse fanbase in the future.

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