Why you can't bring a roast to a rally

A deep dive on comedy, politics, and the importance of context.

Plug: Check out Working Methods, a new 3x/week newsletter filled with quick hit inspiration for creatives from art legends. Coming up: Gems from Leonard Bernstein, Henry Miller, Sylvia Plath, Jim Henson, George Carlin, and more.

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Roasting at a rally

Normally, I’m that guy. Y’know, the comedian who tells people that getting offended at jokes is silly. After all, they’re just jokes. As comics, we are doing our best to get laughs – sometimes it works, sometimes it doesn’t. But the goal is to get laughs. Don’t like a joke? Get over it.

I’ve even written before about why comedians tend to defend each other (it’s not just ‘cuz we’re terrified you’ll come after us next):

Critics can attack how us comics do the job, but they don’t know what it’s like to deal with a hostile crowd, try out an edgy joke, or ride the line between offensiveness and hilarity. They don’t realize the only way to figure out where the line is drawn is by crossing it.

My usual go-to line about it: Intention matters. Did the guy say it in front of a brick wall of a comedy club in order to get laughs? Or did he say it in front of a burning cross at a Klan rally in order to incite hate? Because that’s important.

“This isn’t exactly a perfect comedy setup”

Which brings me to Tony Hinchcliffe’s set at Trump’s MSG rally that generated viral outrage.

The main reaction I had while watching it: Oof, what a hell gig. Tony himself tried to explain why after several jokes didn’t land: “Normally, I don’t follow the national anthem, everybody. This isn’t exactly a perfect comedy setup.”

(Btw, same with Jim Gaffigan hosting that Al Smith dinner. Just an impossible gig. Thinking politicians, Catholic priests, and a comedy roast are a good combination is just insanity. It’s like hiring a death metal band to play a bar mitzvah.)

That’s the thing: Yes, intention matters. But so does context.

I’ve found an important feature of roast jokes is for them to be told at a roast.

See, when you tell jokes at a roast (or a comedy club or standup special), everyone watching knows what’s up. The context is clear.

But when you’re at a political rally, in a suit, standing behind a lectern, with a C-SPAN logo in the corner, in front of a bunch of folks waving signs featuring a hatemonger’s name, amidst a lineup of angry dudes spewing toxic bile, you’ve really messed with the formula.

At that point, the problem isn’t that people can’t take a joke – it’s that they can’t even tell it’s a joke.

Makes me wonder if the N@zis had a comedian at their MSG rally: "Unst zie problem with zie Jews is they can’t take a good roasting. Get it? Oh man, zie snowflaken are gonna hate zis one. But zie only thing better than Der Führer is their furor, am I reich or am I reich? One more? OK, here’s my third reich! Danke schoen!"

(See, I can be offensive too! Btw, I’m a Jew if that makes that any better. No? OK, moving on… 😇)

Basically, comedy showed up where it doesn’t belong. So of course it didn’t go well.

Comedy may seem like a rough and rowdy artform, but it’s actually got a very delicate feng shui. It collapses easily. The slightest misfire sinks the vibe pronto.

Comedians can choose to leave our chicken finger-filled lane, but we do so at our own peril. A skunk in an underground den is right where he belongs. A skunk in someone’s living room stinks up the joint and just makes everyone mad.

Roast rules

Honestly, I don’t understand the appeal of most roast jokes. They usually get over due to cruelty and sneaky turns. And, like late night monologue jokes, they rely on connecting dots, celebs we all know, and shared pop culture references. It all tends to feel like reverse engineered material where gotcha misdirection reigns supreme. I admire folks who do it well, but it just ain’t my bag.

That said, here’s what I know about the typical rules of roasting:

We roast the ones we love. And we roast individuals (not a group). The more famous, the better. And we do it to their face. And then, they get to roast us back. Most importantly, everyone knows they’re at a roast.

All of that seemed to be missing here.

As for the actual jokes: The garbage in the ocean switcheroo was somewhat clever, although a bunch of people from Staten Island and Long Island laughing at another island for being trash is kinda crazy. The watermelon joke (riff?) felt like it was from 1983. And yeah, we know, Jews are cheap. (Btw, why were Jews and Palestinians fair targets, but not Puerto Ricans?)

But picking apart individual jokes is a lame exercise. (I’d hate it if someone did it to me.) Also, the idea that any of this is more outrageous than the stuff Trump says on a regular basis feels bizarre.

None of it should have been a surprise, though. Tony did what he always does (harsh jokes intended to provoke outrage). Whichever moron on the Trump campaign thought it was a good idea to invite him to perform at the rally is the person who should really take the hit.

Set and setting

In the world of psychedelics, people talk a lot about intention, set, and setting. Even if you go into a journey with the best of intentions, a f–d up setting can lead to a f–d up trip. Yet folks often blame the drugs for their bad trip even though the real problem was the environment in which they took them (e.g. every “I had a bad trip at this music festival” story).

At MSG, the intention may have been laughter, but the setting was all wrong. Bro podcast shtick doesn’t work on PBS NewsHour the same way bathroom graffiti doesn’t fly on the walls at MoMA.

There’s also the whole punching up/down thing. See the joke from Tony that went over best:

The other side’s got a lot of crazy endorsements. Swift, Eminem, Leo DiCaprio, Beyonce. Every day the Democratic Party looks more and more like a P. Diddy party.

The crowd roared and Tony noticed:

Oh. Oh, okay. Okay, that’s what you guys want. All right. Heck yeah.

One could argue that actually shows something (gasp) nice about the MAGA folks in attendance. They weren’t onboard for the ethnic trolling bits, but they loved the mocking of famous celebs.

It’s probably why Tony’s set at the Tom Brady roast was more successful. Remember the roast rules mentioned earlier? Going after Gronk to his face is a good time. Attacking entire ethnic groups who aren’t in attendance has a totally different vibe. Even the right wingers at MSG seemed to like it more when he mocked out-of-touch elites as opposed to struggling immigrants and hurricane survivors.

Microfame

There’s also the question of fame. Is Tony some unknown or a big shot? Are these jokes coming from nowhere or is everyone already in on the gag?

Because a common response to all this online has been “I never even heard of this guy.” However, Tony has one of the most popular podcasts in the world, almost 2 million subscribers on YouTube, and recently sold out MSG. (And I’m sure his ticket sales will only increase after all this attention.)

But fame is a tricky beast these days. More and more, show biz is all about microfame. That so many people don’t know who Tony is proves how much we now live in siloed bubbles. Performers can sell out MSG and yet, if asked, 99% of random folks on the street outside the arena would have no idea whom the hell you’re talking about (as discussed by a couple of comedy experts here).

That's never happened before. America used to all watch Seinfeld, Carson, and Kronkite and agree on some version of reality. Now, we all reside in separate circus tents. One man's celebrity is another's "Who dat?"

The main thing you need to know about Hinchcliffe is simply this: He's both very popular and under-the-radar. Which is something you can still say about [Joe] Rogan himself: He has so much reach he can launch new stars like Hinchcliffe. But if you're not tuned to his frequency you might never hear or see him yourself.

That feels like an underrated part of the story too. Tony performed the way he always does for people who enjoy his brand of cruelty. But most of the world still has no idea who he is or what he does. And when all the comedy context clues were removed, it was bound to seem off key. You can’t behave on a first date the way you behave years into a relationship. Yet that’s what we saw at MSG.

The fallout

Of course, the other side, led by Tim Walz, AOC, and Bad Bunny (!), pounced on all this, leading to the usual “that was offensive” vs. “no, you’re just lame” back-and-forth.

Hinchcliffe responded:

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.

Tony’s “I vacation there” defense might legit be the funniest part of all of this. It’s like saying, “I can’t be racist because I’m attracted to black women.” Um, actually… 😬

I don’t really understand provocateurs who are upset when people are, y'know, provoked. No need to be sad about it, you accomplished your mission. Bask in the glow of your successful trolling! If you want the shine, you also gotta take the smoke.

Tony’s response that Walz took the joke out of context is telling. I get where he’s coming from on that; I typically hate it when journalists type out a joke and publish it as if it’s a political statement instead of a joke. My take on that is usually “Of course the joke bombed when you told it.”

But in this case, I’d argue that whomever booked Tony is the one who took things out of context by bringing a roast to a rally. The typical get-out-of-jail card a comedian can play is “Of course I was joking. Look around! It’s a roast!” But when people watched the rest of that rally, why would they think it was a venue for comedy? There wasn’t anything funny about the hatred other speakers delivered there.

I don’t understand provocateurs who are upset when people are provoked. No need to be sad about it, you accomplished your mission.

When you call Puerto Ricans garbage in front of a foaming-at-the-mouth MAGA crowd, who can tell if it’s a joke? There’s a bigger picture here. Is Trump joking when he says he’s going to be a dictator on day one? How about all the other times he said wild stuff and then claimed he was “just joking”? When it comes to politics now, what the hell is a joke anymore and what’s the truth? And how upset can you get at people who can no longer tell the difference?

Woke vs. free speech

We keep seeing comedy stuff framed as a battle between the woke and the free speechers. But that seems like a false choice.

I can’t say I’m with the humorless scolds, but I also think that with power comes responsibility. And when you look at how much comedians and politicians are coming together lately, it’s clear comedians are becoming increasingly powerful.

The left may be too sensitive nowadays, but the right has abused “I was being sarcastic” and “I’m just joking” as excuses. It reminds me of when Jon Stewart tried to claim he shouldn’t be taken seriously because “the show that leads into me is puppets making crank phone calls.” We all knew that was just a lame attempt to have it both ways.

And yes, free speech is vital, especially to comedians. But how can you invoke it as your crucial issue and then support a candidate who wants to throw CBS off the air because 60 Minutes was mean to him? Do you think an authoritarian government is going to be good for comedy? Who’s your favorite comedian from a fascist country? Exactly.

I get it, wokeism has gone too far. But how can comedians kvetch about people getting offended too easily and then complain like a snowflake when people dislike their intentionally provocative jokes?

It all feels like proof we keep slipping further and further from any sort of agreed-upon reality. Now, everything is up for grabs. And it’s tough to say “of course I was joking” when there is no “of course” anymore.

Anyway, I gotta go change my tampon. It’s clogged with the tears of comedians who keep complaining about cancel culture while selling out arenas. And if that offends you…c’mon, I was just joking.

Anyway, here’s my joke about immigrants…

mattrubycomedy

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Quickies

🎯 If we're gonna accept "microaggressions" as legit than I also want to start labelling most complaints as "microtrauma."

🎯 It’s just Manhattan and Brooklyn, but it’s “the Bronx.” That’s why I like to think of “the Bronx” as the “The Ohio State University” of boroughs.

🎯 If you look up "recency bias" in the dictionary, it's just a bunch of yokels arguing Kobe and Lebron were better than MJ.

🎯 My nephew made our family tree at Ancestry.com but accidentally left me out. I asked him to insert me and he said he doesn’t know how to do that. So now I feel like this photo from Back to the Future...

🎯 I don’t like to be called unpopular. I prefer “follower challenged.”

🎯 Tired of people blaming psyche3delics for their bad trips. Nah, you were already on a bad trip. Psychedelics just made you confront that reality instead of continuing to repress it.

🎯 You know who's really into gender essentialism? Every animal in every nature show I've ever watched. We gotta educate these snow leopards about their systems of oppression.

🎯 Nice thing about people who are into vintage clothes is you already know they are low maintenance. If they’re fine with holes in their pants, they’re probably fine with holes in your personality.

🎯 "When you think about it, going bald saves you a lot of money! No shampoo, haircuts, or blow dryer required. It's the best!"
-Me on a flight to Turkey to get a hair transplant

🎯 Will never understand why every restaurant doesn't put something like those up/down mailbox flags on each table so servers know when you need something. It’s. Right. There.

🎯 A manly message re: this election…

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🎯 "There won't be anyone around to restrain Trump this time." That's true. But even scarier: We've never seen what he's like when he doesn't need to win an election sometime in the future. Thus far, we've always seen him needing electoral approval. In a week, that's over and he's unleashed to do whatever he wants. That’s when we really get into IDGAF mode.

🎯 Relationships are tough because if you win a fight you still wind up losing which sucks if you’re good at fighting.

🎯 If an essay, article, or paper can be written by AI, then it is not something that needed to be written in the first place.

🎯 Because it is harder to monetize the written word than it is podcasts/video, we have begun our slow descent back to the idiocy that dominated before the printing press.

🎯 I find access journalism to be less of a problem than access podcasting.

🎯 The bigger the dance floor, the less you should trust the kitchen.

🎯 Next, JJ Redick should let his son coach the Lakers for a quarter.

🎯 Blasé all day.

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Seekers

A mushroom diary excerpt:

So many of us feel lost. But would we even know found if we found it? 

The best way to not get what you want is to never decide what you want. That’s like setting sail without a destination.

So what are you looking for? Where is your destination? Write it down. Every self-help book and productivity guru gives the exact same starter advice: Write down what you want.

There is a hidden secret to that. It forces you to decide what you want. How can you get what you want if you don’t know what it is? Every architect knows the building starts with the blueprints.

“If you have a problem with the third act, the real problem is in the first act,” said director Billy Wilder. The ending isn't working because of the beginning.

In comedy, a punchline problem is usually a setup problem: They didn’t get the punchline because the premise wasn’t clear.

So often, the problem isn’t failure. It’s that we never defined success effectively in the first place. 

(Inspired by a page in my mushroom diary, the notebook I keep during psychedelic journeys. I’ll be doing an entire show about that diary in NYC on November 8 at The Psychedelic Assembly. Tickets available here.)

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Comedy

🃏 Jokes: Get ‘em on my social media: Instagram – TikTok – Threads – X – Substack Notes.

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🃏 NYC weeklies: 1) GOOD EGGS (Mondays) at 7:30pm at NY Comedy Club (Upper West Side). 2) HOT SOUP (Tuesdays) at 10:30pm at Comedy Cellar. 3) GOOD EGGS (Wednesdays) at 8pm at NY Comedy Club (East Village).

🃏 FUNNY HOW: I have another newsletter all about the craft of doing standup. Check it out.

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5-spotted

🗯️ Ethan Hawke on fame and isolation:

Staring at the tabloids, people wonder why celebrities spin off into eccentricity and madness. (As someone who encountered fame at the age of 18, I’ve given this phenomenon considerable reflection.) It has to do with isolation — if you put a human being into any isolation chamber, they will hallucinate. Celebrity is a form of isolation. You are cut off from your community, people react and respond to you in an altered fashion. They give you exemptions from the normal rules of social engagement, they indulge you — and then they resent you for it. You live behind a glass wall — the more people stare, the more alone you feel. Then a snake of madness and megalomania creeps into even the most stable mind. The more fame, the more poison you swallow. The cure, the healing elixir — in my experience — is friendship.

🗯️ Critic Jerry Saltz asks, “What Is a Brooklyn Artist?”

More and more artists have moved further away from artistic centers like New York, as the economics have made living here (even in Brooklyn!) impossible. As long as artists surround themselves with other artists (a must, in my book) and see shows in cities every so often, they don’t need to be in New York per se. Which perhaps is what the migration to Brooklyn was all about anyway: Rather than establishing some new frontier in New York art, it was the first step toward leaving New York for good.

🗯️ @earthlyeducation on Threads:

someone said that "the underlying purpose of AI is for the wealthy to access skill, whilst removing from the skilled the ability to access wealth" and I cannot unhear it

🗯️ A revolutionary idea in the tech world: Try to make money. ATTN co-founder Matthew Segal on the company’s “pivot to profitability”:

There was a moment actually when I realized that un-monetized views were the worst business to be in in the entire world. It was when I went down to Palm Beach, Florida to visit my grandfather, who’s now passed. He was a door and window salesman.

He was like, “Explain your business model.” I’m like, “Well, we’ve raised this venture capital money and we get all these views and then ideally we’re gonna sell to advertisers,” and he goes, “So, are you making or losing money?” I said, “We’re losing money.” He goes, “I don’t understand that. What kind of business loses money?” And I was like, “It’s called venture capital.” He goes, “This is a bad business. You gotta make money, son.” And so I actually kind of had a eureka moment.

🗯️ “The Self-Help Guru for People Who Hate Self-Help” is a profile of Oliver Burkeman:

Maybe we aren’t just afraid to die—maybe what equally intimidates are the real, unvarnished sensations of living: the fear of being unprepared, of letting a pleasant moment slip by, of facing even minor consequences for our actions. By the end of Four Thousand Weeks, he’d arrived at the realization about life that animates this new book—summed up in a favorite quote of his by the Zen teacher Charlotte Joko Beck: “What makes it unbearable is your mistaken belief that it can be cured.” His solution? Develop “a taste for problems,” a readiness to say to yourself, over and over, that problems are “what life is fundamentally about.”

Thanks for reading. Please share it if ya cared for it. ✌️

-Matt