Slackjaw Humor Writing Challenge!

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

Alex Baia
Alex Baia
Aug 14 · 3 min read

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!

First prize winner:

  • $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.

Two runners-up will each win:

  • $500 cash prize, to be invested in bitcoin or spent on groceries.
  • Your piece will be published on Slackjaw and promoted extensively.

Honorable mentions:

  • Are eligible to be published in Slackjaw as paid (Medium Partner Program) pieces and will be promoted on Medium under the “Humor” topic.

Challenge dates

  • 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.)

Meet your judges

These fine folks will be picking the winners…

→ → Enter the challenge now! ← ←

To enter, do all of (1)-(4) below. When you opt-in, I’ll confirm your email, then send you exact instructions for writing and submitting your entry, starting August 21.

  1. Create a free Medium account (if you don’t have one).
  2. Follow Slackjaw on Medium: At the bottom of this story, next to Slackjaw’s logo, click “Follow.”
  3. Follow Slackjaw on Twitter and Facebook.
  4. Click here, and opt-in to the challenge with your best email. I (Alex Baia) will email you right away to confirm that you’re in. Full instructions for writing and submitting your Challenge entry will go live August 21.

Fine print

  • Be sure to do all of (1)-(4) above to qualify. (Note: If you don’t have a Facebook or Twitter account, that’s okay. Please enter anyway, and just note that on your final Challenge submission.)
  • In order to win a cash prize, you’ll need to live in a country where Stripe is available.

Don’t forget to opt-in!

→ Click this link to opt-in now ←

I’ll email you a few updates over the course of the Challenge to keep you in the loop — plus some encouragement and tips — between August 21- September 21. It’s gonna be grand.

I can’t wait to read your Challenge entry!

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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