It’s politics 101: do not hire an insult comic to perform at a rally in the waning days of the election.
But the Trumposphere writes their own rules — at times to their own detriment.
And booking Tony Hinchcliffe — a comedian whose particular skill is ruthlessly roasting anyone with a pulse — to perform at Sunday’s Madison Square Garden rally, was political malpractice.
Hinchcliffe’s now infamous set included a joke where he called Puerto Rico a “floating island of garbage.”
And, well, it’s not good to offend an entire demographic of voters you’re still trying to woo.
The Trump camp distanced themselves from the line and a report in the Bulwark said the bit was ad libbed.
Hey, they were able to catch in the script a joke where Hinchcliffe called Kamala Harris the c-word, which a staffer asked him to remove.
As the right did damage control amidst the uproar, President Biden apparently said “hold my ice cream cone” and decided to defend Puerto Rico’s honor — by calling Trump “supporters” garbage.
The gaffe was reminiscent of Hillary Clinton’s 2016 “basket of deplorables” comment and also brought to mind Obama’s alleged assessment of his Veep’s instincts, “Never underestimate Joe’s ability to f–k things up.”
Bumbling Joe, who is an actual politician and not a comedian, is now doing clean up duty. With a major assist from the media who were outraged by Hinchcliffe just days ago.
In the midst of this stinky mess remains a collective pearl clutching about the initial jokes (which was a reference to PR’s very real garbage problem). Hinchcliffe’s set was not evidence that Trump is a racist.
Having Hinchcliffe on the mic, while unsavvy and imprudent did, however, show someone in the former president’s camp has impeccable taste in comedy.
Hinchcliffe is a take no prisoners roast comedian: an equal opportunity offender who deploys vicious put downs with the accuracy of a sniper. His jokes are cutting and rude. And no creed, no race and no identity will be spared.
His wildly popular “Kill Tony” podcast, where newbie joke tellers perform a minute set for Hinchcliffe and two other established comedians, has 1.9 million subscribers. But his star really rose after Netflix’s roast of Tom Brady, where he put him through an insult clinic.
The Texas based comic said Gronk “looked like the Nazi that kept burning himself on the ovens” and Brady looked like a “Confederate f-g.” Jeff Ross was “so Jewish he only watches football for the coin toss.” He also joked that fellow roaster Sam J is “an obese African American lesbian” thus allowing Netflix to check a lot of diversity boxes.
In other words, there are no sacred cows in the comedy of Hinchcliffe.
As Jon Stewart noted on “The Daily Show” he is, by trade, an insult merchant.
“There’s something wrong with me. I find that guy very funny,” he added.
Because Hinchcliffe is hilarious, and he’s no outlier in the comedy world. The industry’s most popular performers like Bill Burr and Dave Chappelle are transgressive, regularly taking aim at identity.
Burr’s act is filled with race jokes. He pokes at the idea of white male privilege and mocks transgenders in women’s sports — something a majority of Americans believe is a travesty. Chappelle’s 2021 show, “The Closer” landed him in a mess with the trans community.
In an important move, Netflix stood behind him and free speech.
But in 2024 our cultural sensitivities have shifted. DEI is receding and comedy is hitting harder.
This can be seen through Shane Gillis who was hired and fired by SNL in 2019 because he used an Asian slur in an old podcast. Gillis didn’t go meekly into the night. In February, he triumphantly returned to SNL, not as a cast member but a host.
Gillis’ ascent also illustrates the disconnect between what we’re told is supposed to be funny and what Americans actually think is funny.
It turns out, audiences love hearing people speak in public the way many do in private. That, in a sense, explains the appeal of Trump, who can be crude and defies conventional political wisdom that tells candidates to maintain a veneer of politeness. And save the blunt talk for the back room.
No one wants to be coddled and infantilized. They want to hear truths. They want to poke fun at life’s miseries and, sometimes, at themselves.
But for the next time, keep the edgier stuff in the comedy club.
