The worst sin you can commit as a comedian
A deep dive interview with me about comedy, algorithms, meditation, tension, and more.
I had a great Q&A with
and you can stream it here:
Below is Jason’s summary of what went down…
Yesterday, I sat down with Matt Ruby, a comedian who's somehow managed to turn drug experimentation into art, philosophical wisdom into punchlines, and crowdwork critique into a manifesto. What started as a chat about joke writing quickly devolved into an exploration of why we're all slaves to Chinese algorithms, how meditation is the antidote to everything, and why tension might just be comedy's secret weapon.
Matt's an inventive comic. He once did a special called Substance where he performs the same material drunk, high, on mushrooms, and sober – not because he's reckless, but because he's genuinely curious about consciousness. His Substack, Funny How: Letters to a Young Comedian, reads as if Marcus Aurelius decided to become a stand-up comic, and his latest special Bolo proves he's not just thinking about comedy deeply – he's executing it at the highest level in the trenches of NYC comedy clubs.
The Worst Sin You Can Commit
"I think the worst sin that you can do is to be dull," Matt told me early in our conversation. "Just don't be boring." It's a philosophy that extends beyond the stage into his entire approach to art and life. When everyone else is zigging, he’s looking for what he can break to make his comedy zag. Or zog. Or something.
This isn't contrarianism for its own sake – it's strategic differentiation based on supply and demand. "If there's something that everyone else is saying, it's probably not going to be great fodder for stand-up." The result of doing the opposite is comedy that feels like watching someone dig a hole for themselves just to see if they can climb out. As Matt puts it, "Sometimes digging a hole for yourself... if you can get out of it, it's almost like a magic trick element to it."
The Philosophy of Getting Uncomfortable
Matt's approach to tension might be the most illuminating thing about his comedy philosophy. When I mentioned how audiences sometimes seize up at the topic of a joke rather than waiting for the target, he lit up: "To me, that's a golden opportunity. Tension is opportunity."
His analogy is perfect: "Tension to a comedian is what waves are to a surfer." You don't paddle away from waves – you learn to ride them. "Laughter is tension released, so if you've got them feeling tense, that's not necessarily something to run away from."
This isn't just theory. Matt's 2020 special tackled cancel culture not by taking cheap shots, but by genuinely exploring the discomfort around what we can and can't say. The audience doesn't know where he's going, which creates that crucial tension that great comedy requires.
The Substance Experiment: Malcolm Gladwell Meets Morgan Spurlock
Matt's most audacious project remains Substance, where he performed stand-up under the influence of alcohol, weed, mushrooms, and completely sober. As his friend Gina noted, "It makes sense because you have your 10,000 hours in all of those things."
The results were revelatory. Alcohol, he discovered, is "the worst possible drug there is" for performing. "I felt like I had broken a contract with the audience... as soon as the audience hears you slur, all bets are off."
The drunk set was all ego: "I'm doing great, they love this." The mushroom set was complete ego loss: "This is about us, what can we do together?" One drug builds walls, the other tears them down – a perfect window into what these substances actually do to human consciousness.
The Chris Rock Rule and the Death of The Hang
One of the most practical pieces of advice Matt shared came from Chris Rock: "If there's anything that you've talked about three times in your life with someone else, try talking about it on stage." The logic is bulletproof – if you've brought it up three times, you clearly care about it, and that authentic investment is what audiences crave.
Meditation, Mushrooms, & the Pursuit of Presence
Matt's been meditating since childhood – his mom had a meditation room. His joke: "The first time I ever smoked weed, I was like, wow, this smells a lot like my mom's meditation room."
The Crowdwork Apocalypse
Matt has thoughts about the algorithmic dominance of crowd work clips, and they're not pleasant. "It's weird to me that it did pivot into being like a dominant version of the art craft... as perceived online by people who just see it on social media."
The Loud-Soft-Loud Dynamic
Matt's musical background in Chicago rock informed more than just his rhythm – it gave him a framework for understanding comedy dynamics. "I love Led Zeppelin or the Pixies or that sort of loud, soft, loud dynamic and how one buys you the other."
Surfers, Gardeners, and Universal Wisdom
Matt's got theories about who understands the universe best, and they're surprisingly specific: surfers and gardeners. "I think surfers and gardeners sort of understand the universe in some really deep ways that the rest of us can learn from."
The Shamanic Art of Energy Management
Watching Chappelle work a small room gave Matt a revelation about comedy's deeper purpose: "I remember watching him do a set at Comedy Cellar... really feeling like, oh, this is very shamanic in how he's using the energy and playing with it."
The Antidote to Everything
For Matt, live comedy represents something essential we're losing: "I get to be in a room with a room full of people who are not on their screens, who are aligned with a bunch of strangers and who are experiencing joy. And it's like, Oh, thank God... this is how we're supposed to be."
Robot or Animal: Choose Your Future
Matt's vision of the future is stark but oddly hopeful: "I think there's probably some path where you choose between robot or animal in the future." You can have your Neuralink and AI girlfriend and live in virtual reality, "or you'll be an animal who has to deal with human emotions and not knowing stuff and getting lost."
The Holy Grail of Stand-Up
Throughout our conversation, Matt kept returning to what he calls "the holy grail of a good stand-up comedy joke" – material that comes from who you really are, discovered through genuine conversation and real caring. "That's who you are. You're offstage just having some drinks with a friend of yours, and it's what's coming out of you."
The Rebellion of Presence
Despite his concerns about our algorithmic future, he maintains faith in human rebellion: "I think if people are miserable, eventually that bubbles up in a way that they're like, I don't want to do this anymore."
Things we talked about:
Matt Ruby's Comedy Substack: Funny How - Deep dives into comedy philosophy and craft
Matt Ruby's Personal Substack: The Rubes Letter - Essays on tech, mindfulness, and culture
Working Methods - Matt's newsletter on creative process
Matt Ruby Comedy - All his stand-up specials and tour dates
Bolo on YouTube - His latest and best special
Substance on YouTube - The experimental four-part series
Mike Birbiglia's Working It Out podcast - The Ira Glass episode Matt referenced
Waking Up App - Sam Harris's meditation app (mentioned in our chat about meditation)
How to Change Your Mind by Michael Pollan - The psychedelics book that influenced Matt's thinking
Nice dude! Fellow comic here at HECKLE (not sure if you already subscribed!)