Episode
DMA#42: Getting Punched in the Face for a Living with Emily Flake
- Published
- Mar 25, 2026
- Duration seconds
- 141
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Summary
This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.com Trying to succeed as a cartoonist is stupid. 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 . Yo…