Thank you Dana Jeri Maier, Priyanka Jaiprakash ⚘ Poetry, Kato McNickle, Bear Edwards, Tom Murphy, and many others for tuning into my live video with Emily Flake (and Hilary Fitzgerald Campbell!) Join me for my next live video in the app on Thursday at noon when I talk to fellow New Yorker cartoonist Tom Chitty!
Trying to succeed as a cartoonist is crazy. Trying to succeed as a stand-up comedian is masochistic. Trying to do both simultaneously is a clear cry for psychiatric help. Emily Flake does both, and she makes it look infuriatingly easy.
My guest on Draw Me Anything this week is a cartooning powerhouse. She just won the 2026 Thurber Prize for American Humour. She is one of the rare artists whose distinct comic voice translates perfectly from the printed page directly to the stage. She also possesses a genuinely terrifying amount of hustle. Here is exactly how you build an absurd, multi-hyphenate career without completely losing your mind.
The Alt-Weekly Education
Finding your voice requires failure. You need a low-stakes environment to make mistakes, draw weird things, and test boundaries. For Emily, that was the Baltimore City Paper.
She drew a strip called Lulu 8Ball for the alt-weekly. Alt-weeklies are dead now, which is a massive cultural tragedy. They gave artists absolute freedom. Emily figured out a four-beat joke structure, she honed her timing, and she cussed profusely. The traditional papers would never allow that. She is now bringing Lulu 8 Ball back to life on her brand-new Substack. Subscribe to it immediately please and thank you:
The Fraud Detector (Joke in a Box)
Writing jokes is a terrifying puzzle. I arrogantly assumed I knew exactly how to write one. Then I opened Emily’s physical card deck, Joke in a Box.
I read the exercises. I immediately realised I am a total fraud. The prompts are ruthless, practical, and highly effective. Fellow cartoonist Hillary Fitzgerald Campbell actually used the deck to write a joke and ended up selling a cartoon to the New Yorker. You can still buy this box of magic on Bookshop. Do not buy it on Amazon to fund a billionaire’s joyride.
St. Nell’s and the Ghost Hotel
Williamsport, Pennsylvania is a lumber town. It has haunted hotels and a bizarre vacuum of silence. It is also the home of St. Nell’s…
Emily bought a house out there during the pandemic after heading out there and staying in the haunted 100+ year-old hotel, The Genetti, as a little getaway to save her family from murdering each other in their sleep. Her husband told her they had absolutely no money for a second house, so she launched a Kickstarter and raised fifty grand. She turned the property into a free writer’s residency for women and marginalised genders. Three residents stay at a time for two weeks. They write, they sleep, and they create incredible work.
She even launched an entire comedy festival out there called Nellsfest. The town actually shows up and supports the artists. It is a brilliant community. (A lot of medical professionals, as it turns out.)
Longtime readers will remember our eventful booksigning event there earlier this year:
Hell Gigs and Toddler Jazz
Stand-up comedy is an exercise in public humiliation. We brought Hillary Fitzgerald Campbell onto the stream to discuss the absolute worst gigs we’ve ever survived (with emotional scars).
Hillary’s hell gig involved abruptly stopping a family jazz festival. The organisers forced three women to tell dirty jokes to a room full of toddlers. It is the textbook definition of a comedy nightmare.
Emily performed at a children’s play space in Stroudsburg. The audience consisted of exactly one woman sitting on a couch. The woman only spoke Spanish. She stood in a cavernous echo chamber, speaking English into a microphone taped to a stand with packing tape, essentially making bird noises.
My personal hell gig took place in a Williamsport bar. A massive basketball game played on the screens right next to the stage. The bartender connected her phone to the venue’s Bluetooth speakers. She forgot to turn off her keyboard sounds. I tried to tell jokes while the aggressive tap, tap, tap of her text messages blasted through the sound system… more below:
Boxing and Bombing
Getting punched in the face and bombing on stage are the exact same physical sensation.
Emily boxes. I box. Will Sylvince at the Comedy Cellar boxes. The overlap between comedians and fighters is massive. When you take a hit in the ring, it is not the pain that ruins you. It is the disorientation. You have to force your brain to stay in the game while you are completely compromised.
Comedy is identical. When a joke dies, the room turns hostile. You have to stay entirely in control while you are deeply uncomfortable. You eat dirt, you respect the hustle, and you get back up… I’ve written about this before:
Wrestling with glitchy streaming software, cutting through the digital noise, and writing these detailed recaps requires a unique cocktail of intense caffeine and sheer willpower. If you value this virtual bullpen and want to watch the full, unedited video replay of Emily and Hillary drawing live, please consider upgrading to a paid subscription for just $1 a week.
