My caption: “Is it take your dog to war day?” (Contest #486, August 24, 2015)

My caption: “The forecast said localized showers.” (Contest #478, June 8, 2015)

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.”

My caption: “He’s a notorious gagster.” (Contest #480, June 29, 2015)

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:

1. Don’t submit your entry early in the week, late in the week, or in the middle of the week.
2. Don’t go with your first instinct or ponder the cartoon at length.
3. Don’t embrace clever wordplay or avoid it.
4. Don’t go for the obvious or the obscure.
5. 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.