Slackjaw Humor Writing Challenge!

$2,000 in cash prizes and bragging rights to the winners.

Alex Baia
Alex Baia
Aug 14 · 3 min read

The 2019 Slackjaw Humor Writing Challenge is closed. We’ll announce the winners starting October 7, 2019.

You can also Opt-In to the Interest List, and we’ll let you know when the next Challenge happens!

Slackjaw is Medium’s most-read humor publication with 90,000+ followers, and we want your funny writing! We also want to support humor writers — and aspiring humor writers — everywhere. That’s why we’re announcing our first Humor Writing Challenge.

Challenges need awesome prizes, and we’ve got $2,000 in cash prizes for the winners, plus the chance to get your work in front of our judges panel: comedy writers for The Onion, Comedy Central, The New Yorker, McSweeney’s, etc.

We don’t just want any old humor. We want sharp, well-crafted writing where you follow a proven formula:

  • Generate multiple headline ideas and use only the funniest.
  • Get outside your own head by sharing your rough draft with another writer.
  • Sharpen your draft based on 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, we’re going to have you follow a precise idea-generating and re-writing formula to craft a hilarious humor piece. And we’re going to give you the support of our Slackjaw community, so you’re sure to get the help and feedback you need.

On to the prizes!

  • $1,000 cash prize, to be spent or squandered as you see fit.
  • Your winning piece will be published on Slackjaw, and promoted multiple times to our email list of 25,000+ people and all over social media and internally on Medium.
  • Preposterously large bragging rights.
  • $500 cash prize, to be invested in bitcoin or spent on groceries.
  • Your piece will be published on Slackjaw and promoted extensively.
  • Are eligible to be published in Slackjaw as paid (Medium Partner Program) pieces and will be promoted on Medium under the “Humor” topic.

  • August 14 - August 20: Opt-in period. Join the challenge!
  • August 21: Challenge instructions page goes live! If you opted-in, we’ll email you the details.
  • August 21 - September 21: Challenge is live! Get writing. (You can still opt-in.)
  • September 22 >: Challenge closed! You can opt-in to the Future Interest List here.
  • October 7: We’ll start announcing the winners and publishing winning pieces on Slackjaw!

These fine folks will be picking the winners…

→ → Get On The Interested List for Next Time! ← ←

The 2019 Challenge is closed. Jump on the Interest List, and we’ll let you know when we do the next Challenge!

  1. Click here to join the Interested List. I (Alex Baia) will email you right away to confirm.
  2. Be sure to Follow Slackjaw on Twitter and Facebook, and Medium: At the bottom of this story, next to Slackjaw’s logo, click “Follow.”

Alex Baia, Slackjaw editor


Medium humor. Large laughs.

Thanks to Michelle Spies

Alex Baia

Written by

Alex Baia

Writer: McSweeney's, The New Yorker, Slackjaw. Get my best words, delivered monthly, by a majestic falcon:



Medium humor. Large laughs.

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