Caption King
Record-holder Lawrence Wood ’84 shares his secrets to winning The New Yorker Cartoon Caption Contest.
There aren’t many ways to get yourself published in The New Yorker. Long a bastion of the literati, many talented people have found their dreams dashed on the sidewalks in front 1 World Trade Center, the magazine’s home. But there’s no such thing as a genuinely impenetrable fortress. Lawrence Wood ’84, an attorney in Chicago by day, discovered a way in when he first won The New Yorker Cartoon Caption Contest in 2007.
Since then, he has seized the brass ring seven additional times. To put the achievement in context, his next closest competitor has tasted victory a mere three times. Wood has also made it to the finalists’ round an unprecedented 15 times.
The feat is impressive enough that it snagged him another publishing milestone: his own book, Your Caption Has Been Selected: More Than Anyone Could Possibly Want to Know About The New Yorker Cartoon Caption Contest. It hit shelves this summer, gaining acclaim from the likes of Kirkus Reviews, which praised Wood’s talent for “mixing the bizarre, the jocular and the wise into a clever package.”
While the book took about two years to write, Wood has loved words and wordplay since his youth.
“It started with Mad Magazine and the National Lampoon,” he reminisces. “I always loved The New Yorker. I started reading it young. Too young. But back then, it was just the cartoons.”
It wasn’t until arriving at Conn in 1980 that he began reading the articles, too, thanks in part to Conn’s extensive archives. When the Caption Contest went weekly in 2005—it began as a periodic event in 1999—Wood was immediately drawn in. He quickly developed a Monday morning routine around it.
“Oh, it’s a ritual,” he asserts. “I’m very impatient; I’m like a child. I have to get it done first thing.”
The idea for the book came from one of the few who could rightfully lay claim to an even more significant role in the Caption Contest than Wood: contest creator and former New Yorker Cartoon Editor Bob Mankoff.
“He contacted me after I became a finalist the fifth time,” Wood recalls. “He said, ‘We have to ban you now.’ I told him I understood and he said he was joking.”
That joke kicked off a relationship between the two. To start, Mankoff asked Wood to submit 10 cartoon concepts weekly for five weeks. After that, the editor started to connect Wood with other cartoonists at The New Yorker who might be interested in collaborating. Then, Mankoff suggested Wood write a book about his experiences as the winningest caption writer in The New Yorker’s history and include tips on how to, perhaps, beat him at his own game.
“I bragged to everyone that Mankoff had suggested I write the book because I never thought it would actually get published,” Wood says.
But it was, by St. Martin’s Press in June. The book, which features a foreword by Mankoff, takes readers behind the scenes to learn about the contest’s history, the way it’s judged, and what it has to say about humor, creativity and good writing. Wood also wanted to honor the cartoonists who gave him his platform, so he included 175 of The New Yorker’s best cartoons and used most of his $1 million advance to pay the cartoonists for the rights to republish them.
Now that the book’s a concrete reality, Wood has shifted his focus to making it successful. In addition to sitting down with CC Magazine, he’s authored a companion article for The Atlantic, in which his signature humor comes through.
“I have entered more than 900 contests,” he writes, “losing almost all of them.”