Chicago's lord of the riff is king of New Yorker

Larry Wood poses with two cartoons from the New Yorker magazine on May 29, 2009.

To anyone who has encountered New Yorkers' maddeningly internalized sense of superiority about their place of residence, a hubris perhaps best expressed in Saul Steinberg's famous New Yorker magazine cover, "View of the World from 9th Avenue," here is a bit of good news. This also applies to those who take the Chicago-as-Second-City thing a little too personally.

Larry Wood, a lawyer from West Rogers Park, this week became the winner of The New Yorker magazine's weekly Cartoon Caption Contest for a record fourth time, nudging him past a Georgia man who had won the current contest twice and a precursor once.

So, in a sense, the 48-year-old Wood is King of the New Yorker, although not in the same way as, say, E.B. White or John McPhee. In the Steinberg drawing, the almost featureless rest of the country would now have to include, out here in the middle, a Larry Wood Bump.

Wood, supervisory attorney for the Legal Assistance Foundation of Metropolitan Chicago, had a quip for his success in an e-mail announcing the victory to all those he had asked to vote for him: "This means that, during the past five years, I've been published (at least that's what I'm calling it) in The New Yorker more than twice as often as acclaimed short-story writer … Alice Munro. And she thinks she's so great."

I profiled Wood last year after his third win, a story you can find here. This time out, we used e-mail to discuss how he writes a great caption, what it means to do so and whether Wood will now step back and let others have a chance.

Q: How does it feel to have the official, undisputed record in a contest followed mostly by urban elites?

It felt great until you described the contest that way.

Q: Okay, I suppose there are probably some "real Americans" who follow it, too. Seriously, it's quite an accomplishment. Why do you think you've been so successful where so many others have been, essentially, submitting captions into the void?

There's no formula for writing a winning caption, but most of the captions I really admire (and I'm not talking about my own) share four basic elements. They're brief, they're funny, they address everything that's happening in the cartoon and they're suitable for publication in The New Yorker. (The magazine has rejected some truly hilarious cartoons on the grounds that they were too vulgar, and they're in a book called "The Rejection Collection.")

Q: But there's a big gap between understanding what makes a good caption and actually being able to come up with one. Are you a strong visual thinker? Do you work harder at it than others?

Bob Mankoff, who runs the contest, has said that if you've got a talent for the contest, "your brain starts to itch" when you see a captionless cartoon. That perfectly describes the way I feel. I may not immediately think of a caption, but I'm energized by the challenge of finding just the right one, and I can't move on to another task until I've come up with something I'm ready to submit. Sometimes the process involves finding a connection between two disparate subjects (panhandlers and dolphins, or prisons and talk shows). Other times it's a matter of figuring out how the characters wound up in the situation that's pictured, and what one of them might say in that situation. Fortunately, the process usually takes no more than 10-20 minutes.

Q: Describe how you came up with the latest winning caption. I know you are a particular fan of that cartoon.

That cartoon (by Drew Dernavich) presented an interesting challenge because it wasn't as bizarre as the cartoons that are typically chosen for the caption contest. It has no talking cows or panhandling dolphins or anything like that. It's easier (relatively speaking) to caption a strange cartoon, because you're working within very specific parameters. When a cartoon presents a situation that's not inherently amusing or bizarre — e.g., two guys sitting in a traffic jam — your options are nearly limitless. You're working with very little guidance, and that's hard. Winning the last contest, therefore, was particularly gratifying. (Wood's deadpan caption was, "Try honking again.") And now I own a cartoon by Dernavich, whose work I love.

Q: That reminds me. What do you do with the original drawings you've won as the contest's prize?

I get them framed — they come nicely matted but not framed — and hang them on the wall in our front foyer. The frames are expensive, so my wife (who's more fiscally responsible than I) gets a little annoyed every time I win.

Q: Do you think there's any larger meaning to or lessons to be drawn from the contest?

Sure — brevity is the soul of wit. The best captions (and, again, I'm not referring to my own) are the shortest.

Q: What about in the broader social context?

The contest gives people like me, whose work would otherwise never warrant inclusion in the nation's most venerable magazine, a chance to say that they've been published in The New Yorker.

Q: Does your success in this realm ever make you think you could have been a professional comedy writer?

I'd be lying if I said I've never harbored such a fantasy. The closest I've ever come to realizing this fantasy is at The Moth, a story-telling competition held the last Tuesday of every month at Martyrs', a bar on Lincoln Avenue. Every person who wants to compete puts his name in a hat. If your name is one of the ten selected, you get on stage and take no more than five minutes to tell a true story that fits a certain theme. I've competed twice, and though my stories went over well, I only came in third both times. But I'm going to keep competing. After all, I didn't become a finalist in the caption contest until my 39th attempt.

Q: Don't you think you should maybe play it like Miss America, though, and let others have a chance in subsequent rounds?

I don't think my participation in the contest is preventing anyone else from achieving success. … There have now been 260 caption contests and I've been a finalist in just five of them, and I've won only four. So I'm batting 19 (.019), which is a lousy average. I must do better.


Think you are funnier than Larry Wood? Try to beat the expert by writing a caption for this cartoon.