Who Is Tony Hinchcliffe?

And why did he diss Puerto Rico at a Trump rally?

During Ronald Reagan’s second inaugural ball in 1985, the late Don Rickles, often considered the king of insult comedy, lobbed one-liners against high-profile figures in the audience. After being introduced by Emmanuel Lewis, the diminutive actor who was well into his teens when he played a youngster on the TV show “Webster,” Rickles smirked, “That’s the first black kid I ever saw that’ll never play basketball.”

After insulting everyone from then Secretary of State George Schultz to the actor Charlton Heston to President Reagan himself, Rickles quipped, “I make fun of everyone. That’s America.” The crowd seemed to agree.

Fast-forward about 40 years later, when another insult comedian took the stage to support a politician. This time, things didn’t go so well.

Tony Hinchcliffe, co-host of the podcast “Kill Tony,” served as one of the warmup speakers at Donald Trump’s rally in Madison Square Garden in October. The event was already under scrutiny, as some pundits predicted it would be a Nazi-like rally. People were paying close attention to what Trump would say to the crowd, but it turned out he wasn’t the one to create controversy.

[NOTE THAT THE FOLLOWING JOKE CONTAINS ADULT HUMOR]

During his set, Hinchcliffe first took aim at Latinos: “These Latinos, they love making babies too,” he quipped. “There’s no pulling out. They don’t do that. They come inside, just like they did to our country.”

Then he zeroed in on Puerto Rico: “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.”

Hinchcliffe moved on to Blacks, saying that he and a Black man in the audience were carving watermelons together the night before.

Later in his monologue, he suggested the Israelis and Palestinians play “rocky, paper, scissors” to solve their conflict. “You know the Palestinians are going to throw rocks every time and you know the Jews have a hard time throwing that paper. You know what I’m saying?” meaning that Jewish people are often stereotyped as being stingy with money.

The Puerto Rico joke especially landed like a lead balloon. The media quickly ran with the story. Democratic politicians called out Hinchcliffe’s insulting comments, but many Republicans did, too.

U.S. Sen. Rick Scott, a Florida Republican: “This joke bombed for a reason. It’s not funny and it’s not true. Puerto Ricans are amazing people and amazing Americans!”

U.S. Rep. Maria Elvira Salazar, a Florida Republican: Hinchcliffe’s “racist comment does not reflect GOP values.”

U.S. Rep. Anthony D’Esposito, a New York Republican of Puerto Rican heritage: “The only thing that’s ‘garbage’ was a bad comedy set. Stay on message.”

How was Rickles able to insult and get laughs while Hinchcliffe insulted and received groans and backlash? Has our sense of humor changed? Are we more sensitive to ethnic stereotypes? Or is Hinchcliffe just mean and unfunny?

Who is this guy, anyway?

Hinchcliffe grew up in Youngstown, Ohio, and attended Catholic high school, graduating in 2002. According to Wikipedia, Hinchcliffe lived in a tough part of the city’s North Side and roasting people was a way to defend himself. He told Cleveland.com that his abrasive humor got him punched in the face on the school bus.

In 2007, Hinchcliffe moved to LA to try to make it into the comedy clubs. His Wikipedia bio notes that “Hinchcliffe became known at The Comedy Store for insulting other comics and audience members during shows. He is also known for broaching uncomfortable and sensitive topics during his stand-up sets.”

Hinchcliffe’s sharp roasting skills caught the eye of Jeff Ross, host of the TV series “Comedy Central Roast.” He also started to open for Joe Rogan’s comedy shows and became friends with the podcaster.

His joke about Puerto Rico being a floating island of garbage was well-known by Rogan. "I've gotta tell you, that joke kills at comedy clubs. I don't like the joke, [but] it kills," Rogan said during a podcast after the Trump rally controversy. He added that he told Hinchcliffe, “That’s the [joke] that’s going to get you stabbed.”

Roast or insult comedy is nothing new. Through the years, comedians like Joan Rivers, Sam Kinison, Gilbert Godfried, Rodney Dangerfield, Colin Quinn, Lenny Bruce and Ricky Gervais have embraced the genre. The idea is that making fun of other people is, in a sense, making fun of yourself. No one is off-limits. If done properly, insult comedy appeals not only to the witty upper crust but also to the ethnic blue-collar worker.

The key to success seems to be knowing your audience. A bawdy joke that flies in a scrappy comedy club may crash and burn at a large rally that’s also being broadcast around the world. And that’s what happened to Hinchcliffe. The biggest problem with his joke about Puerto Rico is that it didn’t tease about a particular ethnic group; it made fun of an entire island - which just so happens to be part of the United States.

While it was not Trump himself who made the joke, it reflected negatively on his campaign.

This isn’t the first time Hinchcliffe has landed in hot water for insulting jokes. According to Forbes, in 2021 he used a stereotypical Asian accent and called another comedian a slur. Hinchcliffe’s talent agency dropped him, and Rogan removed him from his upcoming shows. Following the blowback, he said in an interview that comedians shouldn’t apologize for the jokes they tell.

Hinchcliffe remained true to that belief, refusing to apologize for his set during the Trump rally. “These people have no sense of humor,” he tweeted on X. “I love Puerto Rico and vacation there.

“I made fun of everyone…watch the whole set. I’m a comedian,” Hinchcliffe added, sounding very much like Don Rickles during his comedy set 40 years ago. It remains to be seen if Hinchcliffe will maintain his popularity as Rickles did or fade into oblivion.