Patrick House in Slate:
Today I can finally update my résumé to include “Writer, The New Yorker.” Yes, I won The New Yorker Cartoon Caption Contest, and I’m going to tell you how I did it. These observations have been culled from months of research and are guaranteed to help you win, too. (Note from Slate‘s lawyers: Observations not guaranteed to help you win.)
Most people who look at the winners of the caption contest say, “I could’ve done better than that.” You’re right. You could have. But that doesn’t mean you could’ve won the caption contest—it just means you could’ve done better. And if your goal is not to win the caption contest, why bother entering? There is one mantra to take from this article, worth its own line break:
You are not trying to submit the funniest caption; you are trying to win The New Yorker‘s caption contest.
Humor and victory are different matters entirely. To understand what makes the perfect caption, you must start with the readership. Paging through The New Yorker is a lonesome withdrawal, not a group activity. The reader is isolated and introspective, probably on the train commuting to work. He suffers from urban ennui. He does not make eye contact. Laughing out loud is, in this context, an unseemly act sure to draw unwanted attention. To avoid this, your caption should elicit, at best, a mild chuckle. The first filter for your caption should be: Is it too funny? Will it make anyone laugh out loud? If so, throw it out and work on a less funny one.
More here. Try to think of a caption for the cartoon above. To see House’s winning caption, highlight the text of this sentence: [“O.K. I’m at the window. To the right? Your right or my right?“]