Doing verbal battle at the O. Henry Pun-Off World Championships.

An illustration from the Tacuinum Sanitatis, from the late fourteenth century. (No pun included.)

The only thing harder than crafting a good pun is finding someone to appreciate it. It’s not that puns are universally reviled—though their critics make it seem that way. It’s just that for every person who loves a clever play on words, there exists another who absolutely despises them; in mixed company, puns are, along with politics and religion, best left alone. If only there were an app that could match people by their senses of humor. Tinder? I barely know ’er!

If it’s difficult to pun profitably in the United States, it’s all but impossible in Mexico, where I’ve been living for the past year. Here I’m limited somewhat by my imperfect Spanish, but also by a lack of fellow punning linguists. There’s not even a word for pun in Spanish, which made it difficult to explain to friends here that after ten months of wasting my presumably hilarious wordplay on their apparently deaf ears, I’d bought myself a ticket to Austin, Texas, to compete in the O. Henry Pun-Off World Championships. Despite its grandiose name, there is no qualifying round ahead of this “championship,” and, with the exception of a lanky Englishman in a chicken suit, all the participants were American.

“So a pun is like a play on words?” a Mexican friend asked before I set out, using the Spanish phrase juego de palabras, that most dictionaries list as the translation for “pun.”

Well, yes, I said, but it’s a specific kind of play on words. I tried to find an example, but I hadn’t realized until that moment just how difficult it is to come up with puns on the spot. The example I offered, which defined the exchange of sex for spaghetti as pasta-tution, didn’t translate as well as I’d hoped.

But punning off the cuff is exactly what’s required to succeed in the Pun-Off’s marquee event. Contestants in the “Punslingers” bracket, facing off in pairs onstage, are given a theme—Disney, weather, et cetera—and forced to make thematically relevant puns every ten seconds or so until one contestant runs out of ideas.

The result, of course, is a series of mostly terrible puns, the sort that elicit the classic weary groan with which puns are so unfortunately associated. “There’s a hook made specially for grabbing people named Ling,” to name one of countless examples. “The GrappLing hook!”

Just as a slam dunk in basketball earns the same number of points as a layup, this portion of the Pun-Off rewards a contestant for the quantity of her puns rather than their quality. As the moderators explained several times, in a refrain later echoed by desperate contestants defending their ripostes, “It doesn’t have to be good. It just has to be a pun.” The Punslingers event may be the only sport on Earth in which the highest level of play is the most painful to watch.

Herein lies the Pun-Off’s ontological dilemma. In real life, the best puns tend to be spontaneous: many are funny in the moment but fail to rise to the higher standard to which we hold jokes that are given time to grow and improve in the course of being committed to paper. And yet the sustained, absolute spontaneity that comes of scraping out pun after pun onstage quickly pulls every contestant down to the bottom of the barrel—a low stratum I think of as “[blank]er, I barely know her” territory.

The closest I’ve come to finding a resolution to this dilemma is in the work of the early twentieth-century humorist Stephen Leacock, to which I was introduced by this year’s Punniest of Show winner Alexandra Petri, who also happens to write a pun-heavy column for the Washington Post. “The inveterate punster,” Leacock wrote, “follows conversation as a shark follows a ship.” What is missing from the Pun-Off, then, is this conversation; onstage, we inveterate punsters are forced to play only with the words we can find inside ourselves, rather than lying in wait for a punworthy moment in the course of normal dialogue. Hence the excess of gimmes like “philosophers Kant hold their liquor,” as opposed to a more organic, transcendent play on words, as when I misremembered the color of a friend’s car years ago and he told me that “it must have been a pigment of my imagination.” Or when a friend interning for a congressman confessed that he snuck a glance at John Boehner’s crotch in a Capitol restroom and I declared him the Peeker of the House. Such turns of phrase are unlikely to appear in any serious writing I attempt down the road, and yet the elation they produce is among my favorite feelings: a credit to their author and a gift to anyone with the wit and good sense to enjoy them.

When it was my turn to take the stage in Austin, however, all that wit and good sense promptly left me—boiled away, perhaps, as the scant shade migrated from my picnic blanket to the lawn chairs and their foresighted occupants behind me. A good two hundred people came to watch us sculpt and mangle the English language in the yard behind the O. Henry Museum, a modest old house wedged between towering hotels in downtown Austin. From under a tent just left of the small stage, a panel of judges doled out their points, but the real power lay with the moderators onstage, whose task it was to confirm that each new volley was indeed a pun, and not a mere cliché or, worse still, the kind of double entendre whose second meaning is derived from suggestive inflection rather than a legitimate play on words. And while, between rounds, the moderators showed themselves to be talented punsters in their own right, the stronger competitors’ deep vocabularies occasionally extended beyond those of anyone else on stage. Playing on the theme of art, for example, one contestant said he’d come up with a better pun if he weren’t so groggy—which, besides describing a state of exhaustion, apparently also names a kind of crushed clay used in pottery. Dictionaries being too unwieldy for a fast-paced live competition, in such moments the moderators have little choice but to take a contestant at her wordplay.

My time on stage challenged no one’s vocabulary, unless someone simply couldn’t find the words to express how quickly I was knocked out of contention. My opponent and I were given the theme of horses, a subject about which I know almost nothing; I opened with a weak joke about “stallion” for time, and before I caught my breath it was my turn again. I mumbled something about a quarter horse that was not quite a pun; the moderators gave me a chance to come up with something better, and after emitting the same faux-contemplative ums and ahs that used to escape me when caught off-guard in a job interview, I threw up my hands and admitted defeat. Despite a lifetime of making and loving puns, not to mention crossing an international border to demonstrate what until recently I called my skills, I’m almost certain I gave the weakest performance of the day.

My poor performance was a predictable result of my inexperience with the relevant kind of pun. Like Leacock’s shark, I follow conversations waiting for a good moment to strike. The constraints of the Punslingers tournament make for something more like a SeaWorld show: a performer can do great things if he’s comfortable with the walls placed around him.

Indeed, my favorite moment of the day occurred during a round in which players had to pun on the theme of “Groups (human and animal)”—e.g., flock, herd, choir, and the like. The two men on stage had exhausted most of the obvious words in the category, and were beginning to butt heads with the moderators as they strayed from proper groups into things like the spaces that hold groups (a stadium, a toolbox) and the plural form of any noun that came to mind (fans, otters), which would have allowed the round to run on indefinitely. After a healthy volley one of the contestants offered an invalid answer, and then another, courting disqualification. And then he rebounded with the perfect pun—not the most clever, not the most original, but one that managed to both keep the round going and poke fun at the increasingly strict moderators: “Next year,” he said, “this topic ought to be band.” Despite the limits on both time and topic, this contestant delivered a pun in the heat of the moment that, against all odds, actually made sense. The crowd went wild, perhaps forgetting for a moment that on Monday they would have to return to a world where words mean just one thing at a time.

Ted Trautman has written for The New Yorker, The Atlantic, Slate, Wired, and others. He lives in Puebla, Mexico.