Comedian Tony Hinchcliffe made a bad joke about Puerto Rico. Will the Trump campaign pay for it?

Tony Hinchcliffe, the popular comedian best known for his brand of offensive humour, caused a stir after speaking at a Trump rally recently — but not for reasons that the Republican party may have hoped for.

Hinchcliffe made racist jokes at the expense of multiple marginalized groups, but it was a joke that compared Puerto Rico to garbage that really caught the internet's attention.

Today on Commotion, comedy reporter Hershal Pandya and Refinery29 Somos deputy director Raquel Reichard join host Elamin Abdelmahmoud to talk about comedy's role in this year's U.S. election.

We've included some highlights below, edited for length and clarity. For the full discussion, listen and follow Commotion with Elamin Abdelmahmoud on your favourite podcast player.

Elamin: We've talked about Tony Hinchcliffe and his incredibly popular podcast, Kill Tony, on this show before. This appearance at a Trump rally over the weekend was his, let's say, hard launch into the mainstream, in a way. Of all comedians that Trump could have picked, why do you think he picked Tony?

Hershal: Over the past few weeks or so, Trump has been aggressively courting a specific voter demo which we'll call the "male podcast listener" demo. And to an extent he succeeded, right? He's hit a lot of the major tentpoles where these people tune into. He went on The Joe Rogan Experience. He went on This Past Weekend w/ Theo Von, went on Andrew Schulz's Flagrant, but the one podcast he didn't go on was Kill Tony. So I guess his campaign figured, why not do the next best thing? Let's get him into our rally.

But the thing with a lot of these podcasters is, they tend to liken themselves to, like, nonpartisan freethinker types, right? The types who wouldn't go to a rally and support one political candidate over another because that's something that "sheep" would do, right? But Tony Hinchcliffe isn't so bothered by that idea. He's been vocally supporting Trump for at least as far back as 2017. He's been doing pro-Trump material on stage, and he likes to play the heel.

Elamin: He wants to be the bad guy in the room.

Hershal: Precisely. And on top of that, he's had a good year. He was on The Roast of Tom Brady earlier this year on Netflix, and he did incredibly well on that. His podcast sold out Madison Square Garden for two nights just a couple of months ago. So you can just imagine the Trump campaign looking at the stats and being like, "This guy talks to the audience we want to get to, why not bring him into the fold? He'll do some roast jokes about Kamala and it'll be great." And then we saw what happened.

Elamin: Can I just say, if you don't know who Joe Rogan is or Andrew Schulz is or who Theo Von is, I want to live on your internet. That sounds like a much nicer place to exist in.

Raquel, Tony Hinchcliffe had a variety of racist jokes in this particular set, but the one that everyone is talking about is the one about Puerto Rico. What did you think when you first heard it?

Raquel: I have a lot of different feelings, to be honest. Immediately, of course, I was angry. I'm a Puerto Rican woman, so hearing anyone denigrate my ancestral land, our people as garbage … this is dehumanizing us in the same way that the United States has done historically, right? We are a colony of the United States, and this language has been used for more than 100 years. 

So, it was infuriating. So was the laughter, right? The joke got a lot of laughs, so it's clear this ideology runs very deep in this party. But the joke itself, I didn't actually think it was that funny. Like, it felt very random to me. It wasn't tied to a particular cultural moment, a news story or anything. It just wasn't good. Actually, what did have me laughing has been seeing Trump, seeing his camp, seeing the Republican Party really try to distance themselves from the joke, and the way in which they're doing that.

Elamin: You're absolutely right. It is way funnier to be like, "We apologize specifically to the Puerto Ricans in swing states," than anything Tony Hinchcliffe said on that stage. 

Hershal, as Raquel mentioned, Trump and his team are now distancing themselves from Tony Hinchcliffe, saying they didn't know what he was going to say. What do you make of that?

Hershal: Are you implying that they would lie, Elamin? They're upstanding patriots!

Elamin: I would never, I'm asking you! You're the comedy reporter among us.

Hershal: The official party line, from what I read, is that the campaign vetted his jokes ahead of time, but that he ad libbed certain lines. They said he ad libbed the line about Puerto Rico, and the one about Latinos and the one about Black people. And whether that's true or not, I can't say for sure. But what I do know is that when you hire Tony Hinchcliffe, you know what you're getting, which is a comedian who steps on lines and then chastises people for being inevitably offended when he steps on those lines, right? And in doing so, he gets to position those people as annoying moralists and scolds, while he gets to position himself as cool and edgy and in support of freedom. 

A lot of Republican identity is wrapped up in this idea more recently, that "this is our identity, and we're being stepped on by the liberals and these woke people." I hate to use that word. So, you know, I think in a sense that's what the campaign bought from him, right? As Raquel mentioned, his jokes played fine in the room. It's only when they went online that people got mad. And then when they got mad, he got to point at them and say they just have no sense of humour, which is what he wrote on Twitter.

You can listen to the full discussion from today's show on CBC Listen or on our podcast, Commotion with Elamin Abdelmahmoud, available wherever you get your podcasts.

Panel produced by Jean Kim.