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How One Chicagoan Keeps Winning the New Yorker Caption Contests

This summer, Loop lawyer Larry Wood, 53, scored a record sixth win in the wildly competitive contest.

Photo: Courtesy of Larry Wood

This summer, Loop lawyer Larry Wood, 53, scored a record sixth win in the wildly competitive New Yorker cartoon caption contest—besting the runner-up by two victories. Here’s how.

1Embrace the weirdness.

“The more bizarre the cartoon is—a dolphin panhandler, cows having tea in a living room—the better the framework you’ll have to make sense of its story. A good caption doesn’t just describe the scene; it adds to it.” (Wood’s solution to that panhandling dolphin: “If he’s so damn intelligent, let him get a job.”)

2Keep it brief.

“One of the best captions I ever saw was a single word: ‘Gesundheit’ [for a needle-covered man standing over a woman lying on an acupuncture table]. Be as short and punchy as possible.”

3Avoid exclamation points.

“Shouting a joke has never made something funnier.”

4Don’t bury the punch line.

“The point of a joke is to build up tension and release it. End with the word that provides the twist that brings the whole meaning of the cartoon together.” (To wit: A woman in a nest says, “It’s only fair. He has a man cave.”)

Check out Wood’s winning captions below (reprinted with permission from the New Yorker).

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