How I Became the Ken Jennings of the New Yorker Caption Contest

When my twin daughters were 10, they created an animated slideshow depicting scenes from our life. One slide showed a cartoon version of me happily daydreaming on the toilet with my pants around my ankles. Above my head they put a thought bubble that read, “New Yorker, New Yorker, New Yorker.”

This got a big laugh, and deservedly so. I have spent much of the past 25 years obsessing over that magazine’s cartoon-caption contest, in which readers compete to supply the cleverest line of dialogue to a captionless drawing. I have entered more than 900 contests, losing almost all of them. But, because I have won eight contests, and made it to the final round in seven others, I hold the all-time caption-contest record. And I might have some insight into how you can beat me at my own game.

Every Monday morning, The New Yorker posts a new captionless cartoon, and every Monday morning, before I do anything else, I stare at the drawing until I’ve come up with at least three ideas. Technically, readers have a week to submit a caption—but I never wait that long. Once I have my three ideas, I send them to a few trusted friends for their reactions. Often they ignore me. Sometimes I don’t even give them a chance to respond, because I simply can’t get on with my day until I’ve submitted my entry.

Clearly something’s wrong with me. The chances of becoming a finalist are infinitesimally small, but that has never discouraged me, even though it should have. In fact, when the contest started in its weekly format, in 2005, I was sure that I would make it to the finalists’ round every week, and every week I was disappointed. Still, I never considered the possibility that I could stop trying. This was partly for the pure love of the game—as the former cartoon editor Bob Mankoff told me, “If you have a talent for the contest, your brain starts to itch when you see a captionless drawing”—but mostly because I wanted to become part of a New Yorker cartoon. I also wanted what the late film critic Roger Ebert, who won the contest 13 years ago after 106 unsuccessful attempts, called the glory of seeing one’s name in the magazine.

I finally won in 2007, when the contest featured a drawing of an angry woman chastising her husband for giving money to a panhandling dolphin. My caption was “If he’s so damn intelligent, let him get a job.”

Winning that contest was thrilling, and my excitement has only grown with each succeeding victory. But I know, because my wife and friends keep reminding me, that not everyone shares my obsession, so I try to pretend I don’t care that much. When I meet new people, I never bring up the contest on my own—deep down, though, I hope someone else will, because it’s all I want to talk about. (You can imagine my delight when an editor at The Atlantic asked me to write this article.)

Read: My friend Jules Feiffer

People often ask me what the trick is to winning. There is no one secret (other than compulsively, doggedly participating every single week), but I have learned a few lessons over the years, some from experience, some from my research for my book about the caption contest. Some are obvious—or ought to be. Make sure, for example, that you understand which character is supposed to be talking. You would be surprised at how many people screw that one up.

The contest is a comic puzzle that typically demands the reconciliation of two disparate elements—prisons and angels, bald eagles and toupees, an anthropomorphic train and a bar—so try to connect them as cleverly as possible. A drawing by Farley Katz showed a group of skydivers plummeting toward the earth. Next to them were the dancers from Henri Matisse’s painting “La Danse.” The winning caption had one of the skydivers saying, “Matisse now; Pollock later.” That’s not only clever—and dark—but really funny.

A particularly effective tactic is to think of a familiar turn of phrase that takes on a new and humorous meaning within the context of the cartoon. One contest featured a drawing of what appears to be a lawyer engaged in settlement negotiations on behalf of a dog. I thought my entry—“He’ll negotiate, but he won’t beg”—was pretty good, but it came in second. The winning caption was superior: “My client is prepared to walk.”

Don’t be vulgar. You can find profanity in The New Yorker, even in some of its cartoons—a Liana Finck classic is set in the Garden of Eden, where Eve is looking at the serpent and saying, “Holy shit—a talking snake!”—but you won’t find such language in the contest. When the New Yorker cartoonist Zachary Kanin worked as Mankoff’s assistant and had what he called the “fun but also soul-crushing” job of reviewing thousands of contest entries every week, he automatically ruled out any that included the word fuck.

Should your caption be funny? Perhaps surprisingly, there’s some controversy around this point. In an article for Slate published not long after I won my first contest, Patrick House, a Stanford-trained neuroscientist who won Contest No. 145, cautioned against submitting anything genuinely laugh-out-loud funny. To do so, he argued, would discomfit the neurotic, introverted New Yorker reader. “Your caption should elicit, at best, a mild chuckle,” he wrote.

I disagreed. Though many winning captions, including some of mine, were merely clever, I thought the best were genuinely funny. Could I be wrong?

Vindication came some years later, when Harry Bliss, who drew the cartoon that was featured in the contest Patrick House won, asked me to caption some of his drawings—and then tossed me aside, as any sane person would, to work exclusively with Steve Martin. When it comes to comedy, who are you going to trust: a neuroscientist from Stanford, or one of the greatest comedians of all time? If the format is funny enough for Steve Martin, it’s funny.

My success in the contest has come with unexpected benefits, including a free MRI (it’s a long story) and the opportunity to contribute, along with several professional humor writers, to Esquire’s annual “Dubious Achievements” feature in 2018. There has been only one drawback. Whenever I meet people who have entered the contest but never made it to the finalists’ round, they ask me to confirm that they were robbed. I always say they were, but I generally don’t mean it. Usually, I agree with the judge who dismissed their submission. Unfortunately, I think they can tell. According to my wife, my voice goes up an octave when I lie.

But I understand these people. Like them, I am convinced against reason that every caption I submit should, at the very least, be selected as a finalist. That unshakable and usually unwarranted confidence in my own work is part of what keeps me entering a weekly contest I almost always lose, and it has been key to my occasional success. It will probably keep me entering the next 900 contests, too.