60 Weeks to 60 — Week 14: Is This Funny?

This week, as part of my 60 Weeks to 60 Challenge, I will attempt to submit a winning submission for the New Yorker Cartoon Caption Contest. I know this is a very very long shot since there have been millions of submissions, and only a few hundred winners. But, it’s worth a try!

This exercise is designed to practice the art of connecting and combining ideas in surprising and humorous ways. I wrote about this challenge in my book, inGenius, and use it with my students, but haven’t tried it myself… Here is an excerpt:

One way to practice connecting and combining ideas is to try your hand at the weekly New Yorker Cartoon Caption Contest. Each week the last page of the New Yorker has a cartoon without a caption. Readers submit captions, and the following week three are chosen to showcase in the magazine. All readers are invited to vote on their favorites.

The cartoons always contain images that rarely go together, are out of place, or are out of scale. It is up to you to find a humorous way to tie the story together. The winning captions combine ideas with the images in unexpected ways. Below are a couple of examples of New Yorker cartoons without their captions. In one, a monster is at a dinner party, and in the other, a hobby horse is in an office. What caption would you create for each?

Matthew May, the author of In Pursuit of Elegance, shared his strategy for winning the cartoon contest. He realized that the odds of winning the contest are about one in ten thousand. Therefore, he had to come up with something truly original. To do this, Matthew wrote a list of concepts or objects that had something to do with the image.

In his case, the cartoon showed a man and a woman in bed wearing protective hazardous material suits. On his list were things such as “bed,” “hotel,” “sex,” “protection,” “germs,” “suit,” and so forth. He then spent five minutes brainstorming about all his associations for those words. Those new associations were then applied back to the cartoon and connected in new ways. Matthew’s winning caption read, “Next time can we just get flu shots like everyone else?

I’m going to try a similar approach this coming week. The new cartoon will be released tomorrow, so I have no idea what it will be. I’ll share my process and the results. You’re more than welcome to join me! May the funniest submission win.


Here is the New Yorker cartoon in need of a caption:

Here is my initial “frame storm.” The goal is to come up with a wide range of possible scenarios. After this, I will begin brainstorming about captions for each of these situations.

Frame Storm of Possible Scenarios

OK… I submitted my caption! Here in another article on why it is so hard to win the contest. First of all, there are well over 5,000 submissions a week. Also, it appears that you have to enter every week. Not sure if that means you are disqualified if you don’t submit every week… Let’s see what happens. :)