Tony Hinchcliffe wasn’t just cruel at the Trump rally. He broke a cardinal rule of comedy | Canada Voices

Even before he started kissing women in the crowd through increasingly small panes of Plexiglas, it had become clear that Carrot Top’s show was not for me.

In 2022, at the insistence of a friend obsessed with ironic bits, I found myself among a guys-trip of men (like a parliament of owls, I believe “guys-trip” is the collective noun) at the Luxor in Las Vegas, the garish hotel-casino that’s as Egyptian as the Bangles. There, the manic prop comic has been holding a residency for nearly two decades – and it showed, as he fired off outdated punchlines about Richard Simmons, the watermelon-smashing Gallagher and Pee-wee Herman’s 1991 masturbation scandal. (Those jokes may well be in his rotation still, even though all three of them have since died.) I checked my watch much more than I laughed.

But I won’t deny that the packed house absolutely loved Carrot Top, with a fervour I haven’t seen before or since. He knew who would give him his biggest laughs and what would tickle them (crude humour that pretends to be middlebrow; jokes that pretend to be apolitical but treat Donald Trump as harmlessly cuddly and prod the left), and then played to them with surgical charisma. He didn’t need me for his show to work. As if to underline the point, as the crowd filed out after the show in red hats and aggressively pro-gun shirts, one man exulted that finally, someone was “doing our comedy.”

Which brings me to insult comedian Tony Hinchcliffe, who found himself at the centre of controversy when he called Puerto Rico “a floating island of garbage” (among other racist and antisemitic remarks) at Trump’s Madison Square Garden rally on Sunday.

But it wasn’t just that his “jokes” were bad – so much so that even the Trump campaign distanced itself from him. He also flubbed a Comedy-101 dictum, and in doing so, sparked this whole furor: He failed to understand his audience.

Over the past five years, Hinchcliffe has become irrefutably famous – he’s sold out Madison Square Garden before, and his Kill Tony podcast is one of the world’s most popular – though our fragmented culture has kept his profile relatively niche. He’s crass and mean, and while he’s also hacky, that’s what’s funny to a good chunk of people now: jokes where the cruelty is the point. That’s their comedy.

It works best in Hinchcliffe’s bread-and-butter venues: roasts, where audiences extend insulters a long leash because they’ve been explicitly primed for viciousness, and more intimate comedy clubs. In one of his signature “savage” clips, as a woman is escorted out of a small-club show after taking offence to a tasteless bit about aborting Helen Keller, he menaces from the stage like a cartoon villain, the crowd deliriously cheering him on: “It’s the dark side now, and I’m telling you … you can’t handle me.” (Hinchcliffe’s brand is cocksure aggression in places where he knows the crowd is on his side, but that’s not anti-woke, transgressive, or brave: that’s finding a safe space.)

It’s easier to be cruel without pushback if you’re doing a set in an intimate club. It’s different when you’re giving a speech at one of the highest-profile events of perhaps history’s most-watched election: The bigger the crowd, the less control you have over how your words will be received. But he clearly wanted to aim big – so it’s on him, not the “humourless left,” that he got a big response. (When aggrieved comedians like Hinchcliffe rail against “cancel culture,” what they’re actually decrying, for the most part, is the feeling of being caught off-guard that more people were listening than the narrow group of people they were thinking about).

Embarrassingly, Hinchcliffe was apparently certain that Trump supporters were his people. Last Saturday, he reportedly rehearsed his Puerto Rico line at a small New York comedy club; when it drew few laughs, he insisted that it would be better received “tomorrow at the rally.” (It wasn’t.) But he should’ve known better. On stage, he admitted: “This is very different than where I’m used to performing.” And he ignored his patron Joe Rogan, who said he warned him about losing sight of his audience: “I tell all comedians, don’t ever do comedy at something that’s not a comedy event.”

You have to know your audience. Comedy turns on expectations: How they’re flipped, played with, ignored. To really play in a sandbox, you have to know where the walls are. If comedians are supposed to be courageous challengers of the social order, as some believe, they need to have a pulse for what society considers sacred. That’s why so many comics talk about the importance of finding your people, especially when you’re starting out.

Today, that’s simultaneously easier and harder. Comedians can acquire fans at the speed of a viral clip, but also find themselves interpreted in unanticipated ways by audiences that are more empowered to speak their mind than ever before. Thinking ahead to avoid that is the modern challenge. Take it from Jerry Seinfeld, who made headlines for comments that “the extreme left and PC crap” were killing comedy, but has since walked that back, acknowledging the best comics understand boundaries and how they shift: “If you’re a champion skier, you can put the gates anywhere you want on the mountain and you’re going to make the gate. That’s comedy. … The game is, ‘Where is the gate, how do I make the gate and get down the hill the way I want to?’ ”

There is a comedic talent, then, in knowing where the gates are – kind of like someone who would laser-focus his jokes while swaddled in Egyptian pastiche in the desert for almost two decades. Grudging respect for Carrot Top? Looks like he got the last laugh, after all.

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