DMA#51: This Wednesday: The Linguistics of a Laugh with Myq Kaplan
Most comedians learn to write jokes. Myq Kaplan got a Master's degree in linguistics first. This either explains everything or nothing, and we're going to find out which.
The first time I saw this week’s guest on stage was over ten years ago. I made the mistake of taking a sip of beer when he walked to the stage. Within twelve seconds of him taking the mic out of the stand, I had IPA shooting out my nostrils and tears streaming down my cheeks.
Here’s something I’ve come to believe after 20+ years of cartooning and 19 years of stand-up: There are people telling funny jokes and funny people telling jokes. Myq is the latter.
The funniest people are not spontaneous. They are precise. The laugh isn’t an accident- it’s the product of someone who has thought obsessively about language, timing, and the exact weight of a single word. Funny people are born, comedians are made.
Which brings me to my guest this Wednesday on Draw Me Anything…
His name is spelt Myq Kaplan
It is pronounced, “Mike.” He is, as far as I can tell, the only stand-up comedian in America with a Master’s degree in linguistics, which, once you know it, makes everything about him make complete sense. The rapid-fire wordplay. The jokes that feel like they’re running three arguments simultaneously. The Substack, Myq Kaplan's Arty Har-Hars, where he writes long, fastidious essays dissecting why a single joke works- going deep into philosophy, spirituality, and language theory just to explain a punchline.
He has been doing stand-up for over twenty years. He placed fifth on Last Comic Standing. He appeared on Letterman, Conan (five times), Leno, Seth Meyers, James Corden, and Louie. He once played Mitch Hedberg in a TV show, which is either the greatest casting decision in comedy history or a genuinely unsettling thought experiment. His album A.K.A. debuted at number one, and the New York Times called it “invigoratingly funny.” He also contributed a track called “How Hitler Saved Christmas” to a Comedy Death-Ray Christmas album.
His newest one-hour special, Rini, dropped for free on YouTube last November. We are absolutely going to talk about why…
Keeping this digital enterprise afloat requires a terrifying amount of unblinking screen time. If you’d like to join the live stream and help fund the three venti Americanos I have to purchase just to trick my nervous system into feeling alive, consider a paid subscription. It’s $1 a week, which is roughly the sales tax on a single bagel in Manhattan.
But here’s the thing that really drew me to this conversation. Myq once went on a podcast specifically to discuss a joke that bombed for the New York Times. Not to explain it away. Not to salvage his dignity. To examine it. That is the act of someone who treats comedy the way a surgeon treats anatomy- with genuine curiosity about what’s inside, even when it’s messy. (And yes, the frog might die in the process, but we just don’t tell the next frog.)
I know do the same thing with cartoons at 2am. I suspect a few of you do it with your own work, whatever that work is…
Anyway, we’ll be talking about…
The linguistics of a joke: What a Master’s in linguistics actually tells you about why certain words land and others don’t, and why most comedians will never be able to articulate what they already know instinctively.
Twenty years of precision: How you build a career on wordplay and philosophy in a culture that increasingly rewards the fast and the loud.
The bombing post-mortem: Myq once dissected a joke that failed in front of the New York Times. We’re going to talk about what you actually learn from a proper disaster.
Spirituality, psychedelics, and the examined life: How a self-described atheist ended up somewhere considerably more interesting, and what that journey has done to the comedy.
I can’t wait for you to meet him.
‘Til then!
Your pal,
PS. If reading this helped you delay opening a message from your mother detailing a distant relative’s gout flare-up, please restack and share it. Word of mouth is the only marketing strategy I can afford.










Looking forward to chatting!