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.
Next you need to know the selection process. The first line of defense at The New Yorker is the cartoon editor's assistant, a twentysomething from Texas named Farley Katz. The cartoon assistant reads every single caption—at least 6,000 per week—and passes his favorite 50 or so to the editors, who narrow the list down to three. If you don't make it past Farley, you will never get your name in print. Knowing how he thinks is crucial. The astute captioner will note that he used to be a rollercoaster operator at Six Flags and a telemarketer. He is an outsider who has never trod in the cemented garden he protects. He had to look up "urban ennui" when he arrived in New York—he didn't learn it riding the subway for 25 years. Exploit the fact that Farley is working off the same stereotypes of The New Yorker readership as you are.
Now that you know your gatekeeper, it's time for some advanced joke theory. Should you make a pun or, perhaps, create a visual gag about a cat surreptitiously reading its owner's e-mail? Neither. You must aim for what is called a "theory of mind" caption, which requires the reader to project intents or beliefs into the minds of the cartoon's characters. An exemplary New Yorker theory of mind caption (accompanying a cartoon of a police officer ticketing a caveman with a large wheel): "Yeah, yeah—and I invented the ticket." The humor here requires inference about the caveman's beliefs and intentions as he (presumably) explains to the cop that he invented the wheel. A non-theory-of-mind caption (accompanying a cartoon of a bird wearing a thong), however, requires no such projection: "It's a thongbird." Theory of mind captions make for higher-order jokes easily distinguished from the simian puns and visual gags that litter the likes of MAD Magazine. To date, 136 out of the 145 caption contest winners (94 percent) fall into the "theory of mind" category.
People read The New Yorker to stay on top of the cultural world if they happen to be smart or—if they're just faking it—in the hope of receiving some sort of osmotic transfer of IQ if they hold the magazine tight enough. Nobody wants to feel that The New Yorker is above them, and the last thing they need is to have a cartoon joke go over their heads, lest they write a whole Seinfeld episode about it. Everyone must get your joke. Use common, simple, monosyllabic words. Steer clear of proper nouns that could potentially alienate. If you must use proper nouns, make them universally recognizable to urban Americans. Excepting first names, only nine proper nouns have ever appeared in a winning caption: Batmobile, Comanche, Roswell, Hell, Surrealism, Tylenol, Bud Light, Frankenstein, Kansas Board of Education. You get the idea. Keep it lowercase, keep it simple.
If you heed these instructions, maybe one day you will get a call from Farley and find yourself a finalist. Now what do you do? First, I Googled my fellow finalists: a legislative director in New York and a public-affairs director in Seattle. Clearly 9-to-5 types, at a loss for time, who would be unable to take advantage of the fact that the contest is decided by an online vote. You can and must do better, preferably by launching a full-scale viral marketing campaign. E-mail everyone you know. Create a Facebook group. Call in longstanding debts. It helps if, like me, you have no shame. I had musicians pitching me at their shows, professors pitching me in their lecture halls, and old ladies at cafes pitching me to their grandnieces. Kiss babies, shake hands, and play to win.
It also helps, of course, if you have the best entry. And I did. Here's the cartoon.
My winning caption: "O.K. I'm at the window. To the right? Your right or my right?"
Mildly amusing at best? Check. Theory of mind? Check. Proper nouns? Nope. And what better archetype of urban ennui could there be than a man in a cardigan holding a drink, yapping on his cell phone while blissfully unaware of looming dangers? A very similar cartoon by Jack Kirby from 1962—similar enough to lead the New York Post to shout plagiarism—has the person inside the window frightened and cowering, sans drink, glasses, or phone. But that was 50 years ago, and drudge and complacency have settled on the urban landscape sometime between now and then. You must look for these themes in your cartoon and pounce.
I will stop analyzing now, in deference to Seinfeld's New Yorker gospel: "Cartoons are like gossamer, and one doesn't dissect gossamer." But what does Jerry know, really? He may have a hit show, millions of dollars, and a beautiful wife, but he has never won The New Yorker caption contest. But I have. I have dissected gossamer. And now you can, too. Good luck.