How to Win the New Yorker Caption Contest

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The New Yorker

We all have our peculiar talents: an uncanny sense of direction, a knack for knowing when to dump a stock, an ability to bake the perfect cake. Larry Wood's forte is winning the New Yorker's Caption Contest, in which readers are invited to submit the perfect quip to accompany the magazine's back-page cartoon. At least 5,000 would-be wordsmiths play the contest each week; of those, three entries are selected by the magazine as finalists, and the winner is chosen in an online vote. On June 1, Wood, a 46-year-old attorney from Chicago, found out he'd captured the weekly contest for a record third time. (Another caption-master has also won three times, though one was under different rules.) Wood spoke to TIME about how to game the contest and how he gets out the vote.

What's your approach to writing these captions?
I come to work on Monday, and the first thing I do is log onto the New Yorker website and check out the cartoon for 10 minutes or so. If something comes to me, I send it in. If not, I usually just give up.

Sometimes something comes pretty quickly. In the first contest I won, [the image] showed a panhandling dolphin, a guy reaching into his back pocket to give him some money, and a woman yelling something at him. I just tried to think about stereotypical things people think about dolphins and panhandlers. Dolphins are intelligent. And one of the most common and nastiest things people say about panhandlers is that they should get a job. And I thought of the caption (registration required). That didn't go over well with my colleagues, because I'm a poverty lawyer.

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The projection you're talking about calls to mind a great Slate article in which a caption-contest winner explained that the trick to winning was using common cliches about the cartoon subject.
A colleague emailed me that article, by Patrick House. That killed me — he had a great caption, but I really loved that cartoon and my caption was almost identical to his, and mine was shorter.

So you could've been a four-time winner.
There could have been 100 people who sent in something along the same lines. There was one time when I turned in what ended up being the winning caption, but perhaps 1,000 people sent it in; I think it was a pretty obvious fit for the cartoon. When more than one person submits the winning caption, they just choose a winner at random. That's just the luck of the draw.

What are the top two or three tips you have for caption writers?
Be brief. Try to incorporate everything that's going on in the cartoon. Sometimes somebody will submit a caption that addresses one thing going on in the cartoon, but not something else that's pretty obvious. I think the more successful captions address everything that's going on. I'll depart from Patrick House here. He said not to try to be too funny. I think you should try to be as funny as you can. He's right that sometimes you see a winning caption that's clever but not really funny. But there are others I've seen — not mine, I hasten to add — that really are terrific and funny. I wish I could say mine were really funny, but I think they fall more into the clever category. You know: "That works."

What else do you think the magazine's editors are looking for in their selection process?
I think they're looking for something that makes them laugh. Sometimes I think they're looking for something out of left field. The ones they like best probably surprise them.

How often had you submitted captions before you had success?
A while. I think I submitted an entry to the first weekly contest. The New Yorker's records show that I've submitted 38 times, but I think it's gotta be more than that. I would've guessed about every other week [out of 192]. The guy I'm tied with, Carl Gable, from Norcross, Ga., won the first annual contest and two of the weeklies; I've won three weeklies. In the annual contest, editors announced the one they liked best, rather than holding an online vote. I actually think that's even more impressive.

Once you become a finalist, do you wage a guerrilla campaign to get the vote out?
Oh, an aggressive one. I'll email everyone in my agency, which has about 200 people. I'm careful to delete from that email group the two or three people that I know hate me, because I don't want them to launch some kind of counter-offensive. I'll email my friends. They'll email some of their friends. I don't know how far and wide that goes, but I email the people I'm in regular contact with. I think you have to do that; I think every finalist does.

How often do you come up with a caption that you're pleased with?
I think about 10 times I've submitted something and thought I might get a call. The odd thing is, I don't think the ones I've submitted that were selected as finalists were as strong as some that were ignored. I don't mean to sound ungrateful. I'm so happy that three of mine were selected as finalists. The last thing I want is for the New Yorker to say, "That ungrateful bastard."

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