larry wood.jpgWe know many lawyers who agonize over the New Yorker magazine’s weekly caption contest, desperately hoping to come up with a gnomic, witty caption worthy of selection. But we know of only one lawyer who has managed to come up with a winning caption three times. Let us introduce you to Larry Wood, an attorney at the Legal Assistance Foundation of Metropolitan Chicago.
Wood, who also teaches a housing and poverty law class at the University of Chicago, has won the weekly contest more often than anyone else. (A slight technicality: A man by the name of Carl Gable has won three times, but one of those was the New Yorker’s annual contest, which has since been replaced by the weekly contests.)
Out of 38 submissions in the four-year history of the contest, Wood’s made it to the finals three times. That’s mighty impressive, given that he’s competing against at least 5,000 other caption entries each week, reports Steve Johnson of the Chicago Tribune. So how’d he do it? Here’s what he told us on the phone this morning:

Short is better. Incorporate everything that’s in the cartoon. In one cartoon I was working with, there was a dolphin and a panhandler. So I thought of all the cliches I could think of about dolphins and about panhandlers. Dolphins are extremely intelligent, etc. Then I came up with the caption that won. My colleagues thought it was a mean-spirited joke for a poverty lawyer to make.

Maybe lawyers have advantages in the caption contests. As one friend of ours noted in response to Wood’s advice, “incorporating all the elements into your answer is actually a skill lawyers are supposed to use in their bar exam essays (and law school tort exams).”
Check out Wood’s winners, including the controversial caption, after the jump.


Wood, a SUNY-Buffalo law grad who grew up in upstate New York, upset some of his Chicago legal aid colleagues with this winning caption. From the New Yorker:
caption contest new yorker larry wood.jpg
Find his other winning captions here and here.
For more advice on writing a winning caption, check out this Slate piece. An excerpt:

[Y]our 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.

So if the above did not make you guffaw, that’s what likely helped it to win.
Chicagoan Larry Wood wins New Yorker Cartoon Caption Contest for record third time [Chicago Tribune]
Chicagoan wins New Yorker contest for third time, friend fears he won’t shut up about it [Romenesko]
Caption Contest #192 [New Yorker]
Caption Contest #123 [New Yorker]


comments sponsored by

39 comments (hidden for your protection) Show all comments