Punny business: When words collide

May 18, 2012, 1:00 PM UTC

Punniest of show: Gracie Deegan

FORTUNE — “When it comes to puns,” John Pollack has written, “many people consider all of them — no matter how clever — to be foolish, irritating, subversive, or worse.”

Pollack is definitely not one of those people. He’s the author of The Pun Also Rises, a book that begins with an account of how Pollack won the 18th annual O. Henry Pun-Off World Championships in 1995 and goes on to link punning, causally, with the dawn of civilization.

I heard him speak last spring at a Mexican restaurant on the south side of Austin. It was the night before the championships (happening again this year on May 19), and some of the contestants had gathered to exchange warm-up puns, drink a little, eat a lot (the tables were groaning too), and honor Pollack as Punster of the Year.

Pollack has pale skin; hardly any hair; shifty, sparkling eyes; and a sudden, winning grin that cuts from ear to ear. He told a story about the time he was one of two finalists for a job as speechwriter for President Clinton. “The decision memo put down these various things,” Pollack said, “but the only thing that President Clinton circled was that I had won the O. Henry Pun-Off World Championships. In the margin he wrote ‘Good!,’ and I got the job.” Pollack’s fellow punsters cheered him as if he were a rock star.

The next day at noon I went downtown to watch the contest on the lawn behind the O. Henry Museum, named for the writer, who lived here for a time and who was fond of wordplay. Pollack, wearing a straw fedora, was on hand to help judge the first event, Punniest of Show. It’s a set-piece format: 90 seconds to rip off as many puns as you can (quantity trumps quality) on a theme of your choosing. The judges score on a scale of one to 10, Olympics-style.

This year’s winner was Gracie Deegan, a petite, brown-eyed 25-year-old rookie who works at the concierge desk at Whole Foods. “I was bagging groceries,” she told me, “and someone handed me a box of mushrooms, and I said, ‘I don’t know, I don’t have mushroom left!'”

Deegan took the stage in khaki shorts and a sleeveless yellow tunic. “WMgeez, y’all,” she began, “I am really worried about the Middle East. This threat is constant and ample. I mean, this is a Syria situation, for Shah! And if we don’t find a solution Sunni, I Farsi that the Shiite is really gonna hit the fan!”

Afterward I sought out Deegan’s boyfriend, Justin Haak. (“It’s German for ‘bad cough,'” Deegan told me.) I asked him, “You don’t compete with her in this arena?”

“Hell, no!” Haak said. “I don’t compete with her in any arena. I’m just trying not to screw up.”

Champions (seated, from left) Matt Pollock, Benjamin Ziek, and Gracie Deegan; runners-up (standing) Dave Wallace, Kelly Dupen, Justin Golbabai, Andy Balinsky, and Jason Epstein

The crowd grew slowly throughout the afternoon in anticipation of the main event, the punslingers competition. It features two or more contestants per single-elimination round; one topic, randomly chosen in the moment; puns parrying puns at maximum five-second intervals until somebody draws a blank. There’s no keening when the end comes, just a dreadful silence.

Back to defend his crown was Ben Ziek, 35, a night auditor at the Burbank Marriott in California and a self-described “game-show geek” who has been on Win Ben Stein’s Money (“I did not, unfortunately”) and Are You Smarter Than a 5th Grader? (“In a way, yes. In a way, no.”)

Ziek — competing in jean shorts, T-shirt, and a black fedora — made it to the final round, together with Dav (don’t call him Dave) Wallace and Jason Epstein. The topic was fairy tales.

“Well,” said Ziek, early in the final round. “I got asked if I have to use the bathroom or if I have to enter the door, so I said, ‘Pee? No. Key? Yo!”

Wallace didn’t miss a beat: “Growing up my mother thought I was gay,” he said. “Fairy? God, mother!”

Epstein smiled appreciatively. “So I have a blow-up cousin,” he began. “And I….” The spectators were groaning. Ziek was looking at him sideways, and Wallace was shaking his head. “Okay, can I finish? I carry her around in my pump kin carriage.”

I was ready to crown Epstein champion. But when his turn came back around, he was done. “I have nothing,” he said sadly, and stepped away from the microphone.

Ziek and Wallace sputtered on, Ziek complaining of a “Disney spell” and Wallace admitting that things were “getting Grimm.” Finally Wallace delivered what seemed like a knockout blow. “Well,” he said, “if I don’t get this one right, after all the insults I’ve given my wife, she’s gonna hit me in the Peter Pan.”

Punster Ella Stankiewicz

Ziek just smirked. “But I know that you’re a crafty man,” he replied instantly. “She’ll never, never land a punch.” Game over.

At this point you might be wondering, What possible connection does any of this have to the world of business? I was wondering the same thing. I asked Pollack to help me out.

When you make puns, he began, “you have to choose your moments, and you have to be willing to let them go if someone doesn’t get your humor. That’s okay. It’s hard when someone doesn’t appreciate it, but if you just let it go gracefully…”

“Most puns are failures,” I said, encouragingly.

“Yes. But so are most scientific ideas, so are most artistic projects. So are most businesses!” Pollack was on a roll. “In the end we don’t decry people for attempting to start businesses or attempting to make art. It’s an act of creation, and that’s bound to have a high failure rate. That’s the essence of evolution, where all these mutations fail and only a very few succeed. That is the nature of life.”

Why, yes. Life is like business. That’s why they call it buyology.

This story is from the May 21, 2012 issue of Fortune.