2020 Slackjaw Humor Writing Challenge (cash prizes & bragging rights)

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2020 Slackjaw Humor Writing Challenge

“$2,450 in cash prizes and bragging rights to the winners”



Slackjaw is Medium’s most-read humor publication — with more than 107,000 followers — and we want your funny writing! We also want to support humor writers, and aspiring writers, everywhere.

Our 2019 Humor Writing Challenge was a big success, with 380 people completing the Challenge. So we’ve decided to bring it back for 2020.

Apply for The Writer Contest (Spring 2020 Short Story Contest)

Challenges need awesome prizes, and we’ve got more than $2,450 in cash prizes for the winners, plus the chance to get your work in front of our judging panel of comedy writers for NBC, The Onion, and The New Yorker.

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 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.

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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 writing community, so you’re sure to get the help and feedback you need.

Contest Prizes

  • 1ST PLACE: $1,000 cash prize, to be spent, invested in cryptocurrencies, or squandered as you see fit.
  • 2ND PLACE: $500 cash prize, to purchase a mid-tier electric guitar, or put a down payment on a 2005 Toyota Echo.
  • 3RD PLACE: $250 cash prize, to purchase two-dozen pints of small-batch, handcrafted, overpriced bodega ice creams.
  • FINALISTS: $100 cash prize each, to be spent on some elegant hardcover books or premium personal hygiene products.
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  • All winning pieces will be published on Slackjaw, promoted to our email list of 30,000+ people, and promoted all over social media and internally on Medium.
  • Incredible, mind-boggling bragging rights to all winners.

Honorable mentions

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

Challenge Dates

  • March 25–31: Opt-in period. Join the challenge.
  • April 1: The Challenge opens! If you opted-in, 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 start announcing the winners and publishing the winning pieces on Slackjaw!

Enter The Challenge

To enter, kindly ensure you do all the following (listed below).

  • Create a free Medium account, if you don’t have one.
  • Follow Slackjaw on Medium
  • Follow Slackjaw on Twitter and Facebook and Instagram.
  • Opt-in to the challenge with your best email.

More Details and Application

When you opt-in, your email will be confirmed (Alex Baia will email you right away to confirm that you’re in) and you will receive the exact instructions for writing and submitting your entry.

Full instructions for writing and submitting your Challenge entry will go live April 1.

Be sure to do all of the steps (1-4) listed above to qualify. If you don’t have a certain social media account, just note that on your Challenge submission.

In order to win a cash prize, you’ll need to live in a country where Stripe is available. See list of available countries here