Many at laptop tells a woman, likely his partner, a litany of things he did instead of writing and doesn’t understand it
“I Don’t Understand It,” Joe Dator via the New Yorker

What Big Bird, Will Ferrell, and Don Draper Taught Me about Writing New Yorker Cartoon Captions

LaTeisha Moore
2 min readMar 12, 2020

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Day 11. I’m tired. Uninspired. I’m cursing my personal challenge to write daily for a month.

I’ve written guides on remote workshops and feedback frameworks, an ode to paint pens, and an anecdote about buying an engagement ring. In my most desperate hours, I ranted about burritos and celebrated CamelCase. With my energy low tonight, I turned my attention to cartoons — New Yorker cartoons.

I thought it would be fun to try my hand at their weekly caption contest. First I needed to know the current cartoon and the rules behind the contest.

  • 250 characters or less
  • One entry per person, e-mail address, or Instagram account
  • Be thirteen or over in age (except employees, etc.)

I could have started from that info, but my research reflex got the best of me. I did a quick search and discovered newyorker.com has a clever Caption that Cartoon series (also on Hulu) where “big-shots try their hand at writing New Yorker cartoon captions.” I’m no big-shot but I’m into the content to prep me for my first caption.

I scroll past Andrew Yang and Danny Devito until I land on few celebs I’m intrigued to learn from:

  • Big Bird and Abby Cadabby, Elmo and Cookie Monster: From these pairs, I’m reminded of the power of brainstorming with others. They model the importance of understanding the full picture (pun!) and being punny. I realize I don’t know who Abby Cadabby is and that makes me old and clearly not a parent.
  • Jon Hamm: “The funny thing about New Yorker captions is they don’t have to make sense or even be funny. They just have to kinda exist in their own weird, world. And it’s really about the pictures, I find.” Peggy Olsen might cringe but I feel empowered by his words.
  • John C. Reilly and Will Ferrell: Their interaction is pure magic. I can hear the staff laughing in the background. After many hilarious captions, they end with “try it yourself at home, it’s not as easy as it looks. If you think you’re so smart, you probably are.” I now feel less confident about my caption-writing potential.

Drumroll, please…

Restaurant server is taking an order from a mouse holding a menu
Chowhound said you had the best Neapolitan

This post is part of my WriteMarch series, a commitment to write daily for a month.

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LaTeisha Moore

Service design lead at an innovation lab inside of a nonprofit closing the opportunity divide in service of the future of work