In March of last year, I wrote about my discovery of—and instant obsession with—the New Yorker’s weekly cartoon caption contest. I have an update: I still haven’t won. Or been a finalist. After entering 58 consecutive times. (Film critic Roger Ebert, prior to his victory, made 107 attempts; that number seemed really big 13 months ago.) A few of my efforts appear throughout this post; the winning entries have invariably been smarter and funnier than mine.
For a particular week’s contest, if your caption is among the three on which the public will vote, you are notified by e-mail—or so I’ve heard. So I was more than a little excited to receive a message from the magazine’s cartoon editor, Bob Mankoff, last Wednesday. But instead of congratulating me on my top-three submission, he was inviting all entrants to use a new ranking tool to help choose the finalists from among the 5,000 entries. Give it a try! It can be addicting—especially if you’re waiting for your own caption to come up, so you can “honestly” assess whether it’s “unfunny,” “somewhat funny,” or “funny.”
Since I started entering, I don’t feel any closer to cracking the nut that is the New Yorker Cartoon Caption Contest. In fact, based on my failure up to this point, I feel distinctly qualified to offer advice on what not to do:
- Don’t submit your entry early in the week, late in the week, or in the middle of the week.
- Don’t go with your first instinct or ponder the cartoon at length.
- Don’t embrace clever wordplay or avoid it.
- Don’t go for the obvious or the obscure.
- Don’t seek out the opinions of others or work in isolation.
In other words, I’ve tried everything. Of course, the best way not to win is not to enter. I won’t not be entering anytime soon.