Slackjaw Humor Writing Challenge 2021
The best humor writing challenge in the universe — with a $1,000 Grand Prize — is back!

Slackjaw is Medium’s most-read humor publication — with more than 135,000 followers — and we want your funny writing! We also want to support humor writers, and aspiring writers, everywhere.
Pioneered in 2019, The Slackjaw Challenge is back for our third consecutive year, in April 2021.
Challenges need awesome prizes, and we’ve got a $1,000 grand prize, plus cool bonuses and runner-up prizes (see below!), and the chance to get your work in front of our amazing guest judging panel: Emma Allen (humor editor, The New Yorker), Scott Dikkers (founder, TheOnion.com), and Jen Spyra (The Late Show with Stephen Colbert).
We don’t just want any old humor. We want sharp, well-crafted writing where you follow a proven formula:
- Generate multiple ideas and use only the funniest.
- Get outside feedback on your draft.
- Sharpen your draft based on that feedback.
These principles are practiced religiously at places like The Onion and taught in top comedy writing schools like The Second City.
In this Challenge, you’ll follow a precise writing process to craft a great humor piece. And you’ll get the support of our Slackjaw writing community, so you’re sure to get the help and feedback you need.
On to the prizes!
Prizes
- 1ST PLACE: $1,000 cash prize, to be spent, gambled on horse races, or squandered as you see fit.
- 1ST PLACE: Win a comedy writing coaching session with Jen Spyra! You’ll have the opportunity to send Jen some of your written work, and your writing career goals, and discuss them with her.
- 2ND & 3RD PLACE: $100 cash runner-up prize, to purchase dinner for two at your favorite sushi place, or dinner for five at your top pizza joint.
- 1ST, 2ND, & 3RD PLACE: Get a dazzling illustration on their winning pieces by Emily Clouse.
- 1ST, 2ND, & 3RD PLACE: Win free enrollment in Scott Dikkers’ brand new online comedy course, How To Write Funny.
- 1ST, 2ND, & 3RD PLACE: Win a signed hardcover copy of Jen Spyra’s Big Time (Penguin Random House), a brand-new collection of raucous, dark, satirical stories.

- TOP 10 FINALISTS & RUNNERS-UP: Are also eligible to be published in Slackjaw as paid (Medium Partner Program) pieces.
- All winning pieces will be promoted to our Yapjaw email list of 30,000 people, and promoted all over social media and internally on Medium in the “Humor” topic.
- Incredible, mind-boggling bragging rights to all winners!
Challenge Dates
- March 15–31: Early opt-in period. Join the challenge.
- April 1: The Challenge opens! If you opted-in (see below), we’ll email you the instructions to do the Challenge.
- April 1 — April 30: The Challenge is live. Get writing. You can still opt-in during this period.
- April 30: Last day to submit your entry.
- Early May: We will announce the winners and start publishing the winning pieces on Slackjaw!
Meet Your Judges
These fine guest judges will pick the winners…
- Emma Allen - Humor & Cartoon Editor, The New Yorker
- Scott Dikkers - Founder of TheOnion.com, Founder of How To Write Funny.
- Jen Spyra - Writing credits: The Late Show with Stephen Colbert, The New Yorker, The Onion. Author of Big Time (Penguin Random House), a collection of raucous, dark, satirical stories.
Plus, the four of us at Team Slackjaw:
- sarah james: @cryingbaseball
- Molly Henderson: @hollymenderson
- Maddie Weigelt: @Madd_dogW
- and yours truly, Alex Baia: @al_baia
→ → The 2021 Challenge Is Closed. Join The Interest List Here ← ←
Join the Future Interested List, and, as soon as we do the next Challenge, you’ll be the first to know.
