Last night’s third place win marks local man’s astonishing fourth showing in the finals for The New Yorker Cartoon Caption Contest

The contest gets between 5,000-10,000 entries per week. Mount Horeb's Paul Nesja won it last year and has been a finalist three times since.
Paul Nesja poses in glasses and a short sleeved striped shirt at his dining room table with four copies of The New Yorker open before him that show his captions.
Courtesy of Paul Nesja.
Nesja at his Mount Horeb home with four of his cartoon captions featured in The New Yorker.
It was likely Shakespeare who first observed there are many routes to greatness. In the case of Mount Horeb’s Paul Nesja and his current brush with cartoon captioning greatness, a chat with his niece provided the path.

“She told me about a contest Bob Mankoff was starting,” Nesja said, when we spoke last week. “She knew I had an interest in cartoons.”

That was spring 2019. Mankoff had retired as cartoon editor of The New Yorker and started a website which included a weekly caption contest like the famous one he’d initiated at the magazine.

Nesja, 58, who with his wife, Christy, has a small design and letterpress printing studio in Mount Horeb, had entered a couple of captions in The New Yorker weekly contest back in 2008. The magazine and its readers pick three finalists and a winner — Nesja heard nothing.

“They went off into the nether regions where bad captions go,” he says.

In 2019, after the heads up from his niece, Nesja entered the contest on the new website, which is currently called CartoonStock.

Almost immediately, he had success. “Within a month, I was a finalist in that one. A month after that, I won.”

His success led Nesja to reengage with The New Yorker contest, which can be addictive, drawing thousands of entrants — weekly estimates range between 5,000-10,000 — and has been known to drive unsuccessful participants a little batty. The late film critic Roger Ebert wrote in 2009 on his Chicago Sun-Times blog that he’d entered the contest “almost weekly virtually since it began and have never even been a finalist. … Just once I want to see one of my damn captions in the magazine that publishes the best cartoons in the world. Is that too much to ask?”

Ebert did finally win — in 2011 — but he’d be shaking his head if he was around to hear about the run Nesja has been on lately.

Nesja won the contest last year. His winning caption appeared in the March 20, 2020 print edition of The New Yorker. The cartoon showed a blindfolded man walking a plank suspended from a rail car, with pirates watching from inside. The caption: “No one crosses the Pirates of Penn Station.”

Then, this past summer, Nesja finished second in the contest for a cartoon that first appeared in the magazine in late July. In September, Nesja’s caption for The New Yorker contest cartoon took third place. (One other time over the summer, Nesja wrote a caption that made the top three, but another entrant had the same caption, and was declared a finalist because his entry was received a few minutes prior to Nesja’s.)

When we spoke last week, Nesja was a finalist again — the third time inside of three months — with the winner to be announced on The New Yorker website at midnight on Sunday, Oct. 17. It was. Nesja placed third.

Nesja knows that consistently reaching the top three in a field of thousands is exceptional, but adds, “I’d like to win first a few more times.”

Nesja’s interest in cartoons dates back to his growing up in Chippewa Falls, where he happened on a 1945 book titled “Cartoon Cavalcade,” which gathered the best cartoons from the leading magazines of the day, including The New Yorker. Other books followed, though Nesja never really dreamed of being a cartoonist. “I’m a lousy artist,” he says. “That was never going to happen.”

Nesja attended the University of Wisconsin–Stout, where he met his wife. The Nesjas have two sons and recently celebrated their 28th anniversary. After living for a time in the Twin Cities, they relocated to Mount Horeb in 2000.

Nesja looks on the caption contests as a hobby. “It’s something I enjoy,” he said. “It’s fun. Some people do a crossword puzzle every day. I do the caption contest.”

What makes a good caption?

“It’s hard to pin down,” he says. “In the cartoon there’s always some incongruency or conflict going on between two elements of the cartoon. The caption should resolve that conflict in a surprising and satisfactory way.”

Nesja currently hosts — with Vin Coca and Beth Lawler — a weekly podcast devoted to The New Yorker cartoon caption contests, and he’s had a chance to interview some of the cartoonists for whom he wrote captions.

Nesja says conjuring a great caption can take minutes — or days.

“If I’m lucky I can think of something in the first five minutes. If I don’t, for the next four or five days I keep notebooks around the house. I write something down, a word, a phrase — something that is relevant to the image of the cartoon. Hopefully, something clicks.”

One other thing helps, Nesja says.

“I’ve always had kind of a bent sense of humor.”

Footer that says Subscribe with covers of Madison Magazine