Not Funny Enough

Tony Hinchcliffe, Puerto Rico, and the lamest complaint in comedy.

“It was just a joke!”

You’ve heard it before. Everyone has.

The story is that on Sunday, during Donald Trump’s rally at Madison Square Garden, a comedian named Tony Hinchcliffe who hosts a popular Austin-based comedy show called Kill Tony (a show that, full disclaimer, I have enjoyed—more on that later) did what comedians do, which was to deliver a joke.

Like all jokes written and told by professional comedians, it was calibrated to provoke a certain reaction.

Some comedians play to the room, meaning they know who’s in the audience and what makes them tick, and they say something that’s sure to get a big laugh. Other comedians, especially in televised and simulcast settings, play to the audience outside the room—the comedian may be aware that the joke is sure to bomb with, or perhaps even anger, the folks within earshot, but that a larger, different audience will eat it up. The most famous, or infamous, example I can think of is Norm MacDonald at the 1998 ESPY Awards. Another setting in which this dynamic often takes hold is the annual White House correspondents dinner, where it’s something of a tradition for the incumbent president and his administration to be subjected to a vicious comedic tongue lashing akin to an all-out roast (e.g. Stephen Colbert in 2006).

What Hinchcliffe did on Sunday night was to play to neither the in- nor out-groups, but to the audience in his head, who quite dishonestly assured him that this was a good joke, sure to be laughed at be somebody. (He even told it at a club the night before, where it apparently did no better). Hear it yourself, if you must.

Basically, after issuing a hearty shoutout to all the Latinos in the house (many of whom are virtually guaranteed to be Puerto Rican, in whole or in part) and registering their whoops, Hinchcliffe likens Puerto Rico—an unincorporated territory of the United States, in fact—to an island of garbage.

Three million people live in Puerto Rico, and about three million more people claim Puerto Rican heritage (a lot of them live in New York City!), making them the largest Spanish-speaking group in the United States after Mexican Americans. They are all American citizens, and none of them are likely to be pleased by Hinchcliffe’s joke, which came amidst a battery of other stereotype-laden remarks about Hispanics, African Americans, and others—few of which, in their mirth-causing capacities, survived contact with the 21st century.

Adding insult to injury, or maybe injury to insult, Donald Trump has been performing better in polls with Hispanic voters than any Republican nominee since 2004. Before the day was out the campaign (but not Trump) had denounced Hinchcliffe’s remarks, and Senator Rick Scott (R-FL) and Rep. Anthony D’Esposito (R-NY) had done the same; before the sun was up the next morning, Trump 2024 spokesperson Karoline Leavitt hit the friendly territory of Fox & Friends to try to limit the damage: “Obviously, that joke does not reflect the views of President Trump or our campaign.” Among many other interesting tidbits, The Bulwark’s Marc Caputo reported that Florida Rep. Maria Elvira Salazar (R) sought an apology from the former president himself.

There is even limited evidence that Hinchcliffe’s act may be stirring votes on the margins, possibly by forcing former fence-sitters like Latin pop superstar Bad Bunny (however famous you assume he is—think bigger) into the breach on Kamala’s behalf.

Whoops!

As it happens, we didn’t have to wait long after Hinchcliffe’s joke for a reaction from the highest-profile boricua in American politics, Alexandria Ocasio-Cortez, who happened to be counterprogramming the Trump rally via Twitch stream at the time with VP pick Tim Walz.

“Who’s that jack-wad?” Walz asks.

“Actually,” an evidently surprised AOC begins, “I think that’s Tony Hinchcliffe, which is super disappointing…” She sounds like she’s about to elaborate more on who he is and how she knows him, before pivoting into a more politically fruitful thread about the joke’s blatant racism and the history of Puerto Rico.

What I suspect is that beyond living in New York and supporting Bernie Sanders’s runs for president, AOC and I have in common the fact that we have both watched and enjoyed Kill Tony—and not despite Hinchcliffe, who is a serviceable shock-jock host who asks good questions of the wannabe comedians who come on the show. It’s a simple format: dozens if not hundreds put their name in to get up on the Kill Tony stage and tell jokes before Hinchcliffe and his co-hosts attempt to razz and, more often than not, humiliate them. It’s crude, relentlessly mean-spirited, and often very funny.

Which is to say that contrary to much of the last days’ commentary, Hinchcliffe is actually a pretty effective comic in the right format. He keeps things running more or less smoothly on KT, and positively stole the show at Netflix’s Roast of Tom Brady, such that other people—not me—who had seen it said only to watch Hinchcliffe’s segment (that was, they said, the only good part).

Which brings us back to Sunday’s mishap. Surprised to be taking fire from ostensible friendlies, Hinchcliffe, while at the lectern, played the enfant terrible, smiling and trying to channel the audience’s negative response back into his routine (Wow, you guys didn’t like that one, hehe, well how about this next one…). When he actually left the stage and it must have finally began to dawn on him how badly he’d fucked up, Hinchcliffe decamped to X, taking a hasty shot at the politically convenient targets of Walz and AOC:

These people have no sense of humor. Wild that a vice presidential candidate would take time out of his “busy schedule” to analyze a joke taken out of context to make it seem racist. I love Puerto Rico and vacation there. I made fun of everyone…watch the whole set. I’m a comedian Tim…might be time to change your tampon.

Zing.

Now, unlike certified Puerto Rico-enjoyer Tony Hinchcliffe, I’ve never actually been to the island. But I do have some exceedingly modest connections to that place. As a college reporter, I interviewed about half a dozen of my fellow students in the aftermath of Hurricane Maria, writing about how they were staying in touch with family and loved ones after the massive damage and blackouts inflicted by the storm. I learned a few other things, too; about how some, often more politically activist folks, call it the “world’s oldest colony” and seek for it full sovereign status; how many more prefer US statehood and its attendant benefits, like two Senators in Congress and enough electoral votes to make pandering to Puerto Ricans, and even seeking redress of their actual needs, a politically useful task.

At three million-plus, Puerto Rico already has more residents than some twenty-something US states, and a much larger proportion of island-bound Puerto Ricans live beneath the poverty line than in most US states—a fact that surely has something to do with the profound democratic deficit under which they live.

If mocking the less fortunate than oneself is “punching down”—and, therefore, off-limits to the socially conscious comedian—then Tony, while remaining inside the bounds of the US, could hardly have reached lower with his fist. But like AOC, apparently, I’ve seen Hinchcliffe’s punching-down act before. He never isn’t punching down. But usually there are some laughs in the mix.

Face it, buddy—like any of those poor fools you mock so tirelessly at your open mics, you bombed. Hard.

You bombed before an audience that was primed to love your shtick, and in doing so you hurt, in some small but appreciable way, the political cause of the man you claim to adore. In the very same stroke, you undermined whatever exceedingly flimsy claim to a humanist, democratic universalism that Trump—in his campaign of constantly promoting racist tropes while effectively dodging, in the eyes of much of the voting public, the charge that he, himself, is a racist—had managed to preserve.

And then, you—the same one who, like the rest of your anti-woke comedy milieu, professes to be above the scolding of the left; who lets punches fly, land where they may—got mad online about the entirely foreseeable backlash to the joke that you told.

By all means, do edgy comedy. Poke fun at liberal pieties, shock people. Punch down. Given the runaway success of Kill Tony, and the different political stripes of those who watch, there’s clearly a market for that. But just remember, at the end of the day, you have to make them laugh.