All winners from the 2021 Challenge…

Image by Emily Clouse

The Slackjaw Humor Writing Challenge was a 30-day comedy writing challenge extravaganza, open to all. After reading and re-reading the 482 entries, our panel of judges has reached a consensus.

Here they are: the winners. Thanks to all who completed the Challenge. We had a blast reading!

Alex Baia, Sarah James, Molly Henderson, Maddie Weigelt
Team Slackjaw

The Winners

  1. (First Place) We Are ZIPIT™ Convertible Pants, And This Is Our Application To Become The Official Convertible Pants Of The Chicago Cubs by Tracy Silagi
  2. (Second Place) Frequently Asked Questions About 4% Jazz, The World’s Only Radio Station That Plays 4% Jazz by…


We feature a new humor theme every couple of months. Slackjaw’s current featured theme is Sex and Dating!

(Learn about submitting a featured theme piece in our submission guidelines.)


Illustration by Emily Clouse

We feature a new humor theme every couple of months. Slackjaw’s current featured theme is Generations!

(Learn about submitting a featured theme piece in our submission guidelines.)


All winners from the 2020 Challenge!

Illustration by Emily Clouse

The Slackjaw Humor Writing Challenge was a 30-day extravaganza of focused comedy writing, open to all, with $2,450 in cash prizes. After reading and reading and reading (and re-reading) the 476 (!!) entries, our panel of judges has reached a consensus.

Here they are: the winners of the 2020 Slackjaw Humor Writing Challenge — which we are revealing one-by-one, starting May 11.

Thanks to all 476 writers who completed the Challenge. We had a blast reading!

Alex Baia & sarah James, Slackjaw Editors.

The Winners

  1. I’m A Man’s Man, And I Await The Return Of My Man by Amanda Lehr (1st Place…


A few of our recommended resources for humor writers

Humor Newsletters

  • Hyoom (Slackjaw Editor Alex Baia’s Humor Newsletter) - Alex will send you occasional written amusement, plus a few of his favorite Slackjaw pieces, once a month. You get the Ultimate Humor Writing Cheatsheet when you join!
  • A Newsletter of Humorous WritingFrom the hosts of New York’s celebrated show, An Evening of Humorous Readings. Luke and James round up some of the best humor writing on the web. Don’t miss this weekly delight!
  • Satire and Humor Festival - The Satire and Humor Festival is a twice-a-year festival and a year-round humor writing community. Stay in the loop!

Online Courses


Photo by Kelly Sikkema on Unsplash

Behold the only opinion that matters: The editors’ picks for our favorite 10 posts of the year.

Seasons greetings, Slackjawers! Earlier, we shared the top viewed posts submitted to our humble little publication this past year. They’re fantastic and hilarious, and if you haven’t read them already, you should check em out!

Now, if high school has taught us anything, it’s that life is more than just a popularity contest. (Another lesson: changing the font to Courier New easily turns a one-page essay into, like, two or three pages.)

So here, we’d like to spotlight 10 of our personal favorite posts of the year, as chosen by the editors.

Get more comedy from all our writers by…


You, the Medium comedy fans, have spoken. Presenting our 10 most viewed and read pieces of the year.

1. A Realistic Guided Meditation by Alex Baia

You wish that skinny jeans were comfortable. Or that non-skinny jeans were fashionable.

But fashion is fickle. What else is fickle? I don’t know… Bears?

Bears like honey. Honey. Bees. Things that fly. Airplanes. Pterodactyls. Dinosaurs went extinct. That meteor did it: Chicxulub.

Sit with the idea that a rock named “Chicxulub” killed the Pterodactyls.


A Slackjaw Exclusive Book Preview, from Author Sarah Cooper

Sarah Cooper is a writer, comedian, and creator of the satirical blog The Cooper Review.

We’re thrilled to present an exclusive sneak preview from her new book, How to Be Successful Without Hurting Men’s Feelings.

CHAPTER 2: COMMUNICATION

How to Talk Like a Man but Still Be Seen as a Woman

In male-dominated workplaces, women must join The Boys Club. That means acting more like men and less like women.

However, sometimes when women say the exact same thing a man says it’s interpreted in a completely different way. …

Slackjaw

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