I'm talking to the winner of the 2026 Thurber Prize for American Humor tomorrow - Emily Flake!
Yes, the guest I've been wanting to have on since Day #1 is finally on Substack...
Tomorrow, I get to escape the tech deluge and talk to one of my absolute favourite people on Earth. We are going live at noon for Draw Me Anything Episode #42 with my dear friend and fellow idiot who is insane enough to do both stand-up comedy AND cartooning, the brilliant Emily Flake!
If you are somehow unfamiliar with her work, Emily is a cartoonist for The New Yorker, an illustrator, an author, and a remarkably talented comedian. I have written about her before in my ‘Someone You Might Like’ dispatch, but attempting to distil her career into a single paragraph is basically impossible.
She has this incredibly distinct, hilarious voice in her cartoons that perfectly matches her voice on stage. In fact, she was one of the very first cartoonists I ever met who also did stand-up comedy. I’m deeply jealous of how seamlessly she translates her comedic brain from ink on a page to a microphone in a dank basement.
Just last Thursday, I was up at the Society of Illustrators for a screening of Liza Donnelly’s fantastic documentary about New Yorker cartoonists, Women Laughing (which I wrote about here). Emily is featured heavily in the film, and her on-screen moments pulled some of the biggest, most genuine laughs from the entire packed house.
Speaking of accolades, I mentioned in my latest newsletter that Emily was just awarded the 2026 Thurber Prize for American Humour in Cartoon Art. (Roz Chast won the very first one of these back in 2024).
But perhaps the most impressive thing Emily has built over the last few years is St. Nell’s. It is a humour writing residency for women and marginalised genders located in Williamsport, Pennsylvania. (Williamsport is a tiny, charming city on the Susquehanna River, mostly known for the Little League World Series until Emily decided to turn it into a comedy Mecca.)
Related:
Back in October 2023, Emily organised Nellsfest, an entire comedy festival built around the residency. We previously went down there and did a ‘full tour’ in Williamsport, performing stand-up together in local venues like The Brickyard and the local theatre. It was an absolute blast. St. Nell’s is an incredible resource. It houses three residents at a time, completely free of charge, giving writers the time and physical space to actually do the work. They get to focus entirely on stand-up, satire, cartooning, or whatever humorous project they are trying to wrestle into existence without the usual crush of daily life getting in the way. (Photos by the amazing Mindy Tucker)
Here’s something nice that fellow New Yorker cartoonist Tom Toro wrote about Emily last week — he’s better at this than me.
Tomorrow, we are going to sit down, scribble wobbly lines, and talk about all of this. We will cover the Thurber Prize, the absolute grind of stand-up comedy, building a residency from the ground up, and how to stay sane as an artist in a completely absurd industry.
Putting these live streams together, wrestling with glitchy broadcasting software, and trying to convince the internet to pay attention requires a unique cocktail of intense caffeine (whiskey) and sheer willpower. If you want to join the live stream, request a drawing, and help repay the labour of making this digital monastery run, please consider upgrading to a paid subscription for just $1 a week. It keeps the lights on, keeps the Wacom tablet charged, and keeps Morris supplied with the unnecessarily expensive dog food he demands.
Grab a coffee, charge your plastic stylus, and tune in tomorrow (Tuesday the 24th) at noon Eastern time.
Now, if you will excuse me, I need to go open a window before Morris suffocates me with his toxic farts.
‘til next time!
Your pal,
PS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads.
