From the moment he spoke, I knew I was screwed. On the surface, the guy wasn’t particularly fearsome—pudgy, late thirties, polo shirt, plaid shorts, baseball cap, dad sneakers—but he looked completely at ease. One hand in his pocket, the other holding the microphone loosely, like a torch singer doing crowd work. And when he finally began talking, it was with an assurance that belied the fact that he was basically spewing nonsense.

“I hate all people named John,” he said with surprising bravado. “Yeah, that’s right, that was a John diss!” The crowd roared. John-diss. Jaundice. A glorious, groan-inducing precision strike of a pun.

Welp, I thought. It was fun while it lasted.

If you’re an NBA rookie, you really don’t want to go up against LeBron James. Anyone’s trivia night would be ruined by seeing Ken Jennings on another team. And if you find yourself at the world’s biggest pun competition, the last person you want to face is four-time defending champion Ben Ziek. Yet that’s exactly where I was, on an outdoor stage in downtown Austin, Texas, committing unspeakable atrocities upon the English language in front of a few hundred onlookers who were spending their sunny May Saturday reveling in the carnage.

The rules of the 39th annual O. Henry Pun-Off World Championship’s “Punslingers” competition are simple: Two people take turns punning on a theme in head-to-head rounds. Failure to make a pun in the five seconds allowed gets you eliminated; make a nonpun or reuse a word three times and you’ve reached the banishing point. Round by round and pair by pair, a field of 32 dwindles until the last of the halved-nots finally gets to claim the mantle of best punster in the world and what most people would agree are some pretty dubious bragging rights. It’s exactly like a rap battle, if 8 Mile had been about software engineers and podcasters and improv nerds vying for supremacy. (Also just like 8 Mile: My first-round opponent had frozen when his turn came to pun on waterborne vehicles. Seriously, yacht a word came out. Canoe believe it?)

Eventually, there we stood, two among the final eight: me, a first-timer, squaring off against the Floyd Mayweather of the pun world. Actually, only one of us was standing; I found myself doing the world’s slowest two-step just to keep my legs from trembling. I’d been a little jittery in my first couple of rounds, sure, but those were standard-issue butterflies, perched on a layer of misguided confidence. This was the anxiety of the sacrificial lamb. I was punning above my weight, and I knew it. Once the judges announced that we’d be punning on diseases—hence Ziek’s joke about star-crossed livers—we began.

“Mumps the word!” I said, hoping that my voice wasn’t shaking.

Ziek immediately fired back: “That was a measle-y pun.” Not only was he confident, with a malleable voice that was equal parts game show host and morning-radio DJ, but his jokes were seemingly fully formed. Worse, he was nimble enough to turn your own pun against you.

“Well, I had a croup-on for it,” I responded. Whoa. Where’d that come from?

He switched gears. “I have a Buddha at home, and sometimes”—making a rubbing motion with his hand—“I like to rubella.”

I was barely paying attention. Diseases, diseases—oh! I pointed at people in different parts of the audience. “If you’ve got a yam, and you’ve got a potato, whose tuber’s closest?”

“There was a guy out here earlier painted light red,” Ziek said. “Did you see the pink guy?”

“I didn’t,” I responded. “Cold you see him?”

Again and again we pun-upped each other, a philharmonic of harmful phonics. From AIDS to Zika we ranged, covering SARS, migraines, Ebola, chicken pox, ague, shingles, fasciitis, streptococcus, West Nile, coronavirus, poison oak, avian flu, gangrene, syphilis, and herpes. Almost five minutes later, we’d gone through 32 puns between the two of us, and I was running dry. As far as my brain was concerned, there wasn’t a medical textbook in existence that contained something we hadn’t used. Ziek, though, had a seemingly endless stockpile and tossed off a quick alopecia pun; I could have bald right then and there. The judge counted down, and I slunk offstage to watch the rest of the competition—which Ziek won, for the fifth time. Knowing I’d lost to the best cushioned the blow, but some mild semantic depression still lingered: Instead of slinging my way to a David-like upset, I was the one who had to go lieth down.

Author Peter Rubin doing the punning man. Ryan Young

When I was growing up, my father’s favorite (printable) joke was “Where do cantaloupes go in the summertime? Johnny Cougar’s Melon Camp.” This is proof that—well, it’s proof that I grew up in Indiana. But it’s also proof that I was raised to speak two languages, both of them English. See, there’s the actual words-working-together-and-making-sense part, and then there’s the fun part. The pliant, recombinant part. The part that lets you harness linguistic irregularities, judo-style, to make words into other words. It’s not conscious, exactly; it just feels at some level like someone made a puzzle and didn’t bother to tell me, so my brain wants to figure out what else those sounds can do.

A lifetime of listening to hip hop has reinforced that phonetic impulse. Polysyllabic rhymes aren’t strictly puns, but they’re made of the same marrow; when Chance the Rapper rhymes “link in my bio” with “Cinco de Mayo” in the song “Mixtape,” I get an actual endorphin hit. Besides, rap is full of puns already: instant-gratification ones—like Lil Wayne saying “Yes I am Weezy, but I ain’t asthmatic” or MF Doom saying “Got more soul than a sock with a hole”—as well as ones that reveal themselves more slowly. Kanye West might be more famous for his production than his lyricism, but he endeared himself to me forever on the song “Dark Fantasy” by spitting the best Family Matters pun of all time: “Too many Urkels on your team, that’s why your wins low.”

I was punning above my weight, and I knew it.

Whether this is nature or nurture, though, the end result is the same: I’m playing with language all the time, and Kanye and I aren’t the only ones. “I can’t listen passively to someone speaking without the possibility of puns echoing around in my head,” says Gary Hallock, who has been producing and hosting the O. Henry Pun-Off for 26 years. He’s seen the annual event grow from an Austin oddity to a national event and watched dad jokes, of which puns are the most obvious example, take hold in the millennial consciousness; a dad-joke-devoted Reddit board boasts more than 250,000 members. “I’ve often compared punsters to linguistic terrorists,” Hallock says. “We’re literally stalking conversations, looking for the weak place to plant our bomb.”

And we’ve been doing it for a long, long time—verbal puns date back to at least 1635 BC, when a Babylonian clay tablet included a pun on the word for “wheat”—and the world has been conflicted about them for nearly as long. (Linguists can’t even agree whether the word pun derives from French, Old English, Icelandic, or Welsh, though there’s no point heading down that scenic root.) On one hand, puns are the stuff of terrible children’s joke books. Oliver Wendell Holmes likened punsters to “wanton boys that put coppers on the railroad tracks. They amuse themselves and other children, but their little trick may upset a freight train of conversation for the sake of a battered witticism.” On the other, God, how can you not feel a little thrill when you make a good one or a begrudging joy when you hear a better one?

Humor theorists generally agree that comedy hinges on incongruity: when a sentence or situation subverts expectations or when multiple interpretations are suggested by the same stimulus. (Also, yes, humor theorists are a thing.) That stimulus can be visual (looking at you, eggplant emoji!) or auditory (what up, tuba fart!); most commonly, though, it’s linguistic. Language is slippery by nature, and of the many kinds of wordplay—hyperbole, metaphor, spoonerisms, even letter-level foolery like anagrams—nothing takes advantage of incongruity quite like puns, of which there are four specific varieties. In order of increasing complexity, you’ve got homonyms, identical words that sound alike (“Led Zeppelin’s guitarist was interrogated last week, but detectives weren’t able to turn the Page”); homophones, which are spelled differently but sound the same (“I hate raisins! Apologies if you’re not into curranty vents.”); homographs, which sound different but look the same (“If you’re asking me to believe that a Loire cabernet is that different from a Napa cabernet, then the terroirists have won.”); and paronyms, which are just kinda similar-sounding (“I have a ton of work to do, but I ate so much cucumber chutney that I have raita’s block”). When we hear a pun, the words we hear aren’t the words we think we hear, and the burden’s on us to crack the code.

Granted, there are people out there who hate puns, and maybe rightly so. But for many of us, that decryption process is a reward unto itself. “Humor happens when something important is being violated,” cognitive scientist Justine Kao says. “Social norms, expectations. So for people who are sensitive to the rules that language follows, puns are more entertaining.” In other words, if you work with words on a daily basis—writing, editing, translating—you’re simply primed to appreciate them more. Behind every great headline, any editor will tell you, is a great pun. (I have a colleague at WIRED who once looked at a page about chef’s knives and gave it the headline “JULIENNE MORE”; people lost their goddamn minds.)

Still, even among the nerdiest of word herders, there are some rules. Two years ago, Kao and two colleagues at Stanford and UC San Diego decided to prove empirically that incongruity was the root of humor. They tested people’s reactions to hundreds of sentences that varied from one another in minute ways. Some used homophones; some didn’t. Some added detail supporting the nonpun interpretation of the sentence; some stripped detail away. They were able to demonstrate that ambiguity of meaning is necessary for a pun to be perceived—but it’s only half of the equation. (And literally, there’s an equation.) After all, “I went to the bank” is ambiguous, but it’s not a pun. The true determining factor of a pun’s funniness is what the team calls distinctiveness.

Take the sentence “The chef brought his girlfriend flours on Valentine’s Day.” It’s a homophone, so it’s not the most complex pun. But if you turn the chef into a pastry chef, that added vocation property makes the pun more distinctive. “When you’re able to identify keywords from different topics,” Kao says, “it clues you in on the intentionality of it—you’re forcing together two things that don’t often co-occur.”

Of course, “The pastry chef brought his girlfriend flours on Valentine’s Day” still isn’t funny. It’s the kind of pun a bot would make, and maybe has made in the decades since programmers created the first pun generator. There’s no storytelling to it, no drama. A good pun isn’t just an artless slab of sound-alikeness: It’s a joke that happens to hinge on wordplay. A truly formidable punner knows that and frames a sentence to make the pun the punch line. The longer you delay the ambiguity, the more tension you introduce—and the more cathartic the resolution. A pun should be an exclamation point, not a semicolon.

But was I a truly formidable punner? I’d thought so—hell, my lifelong dream is seeing Flavor Flav and Ellen Burstyn cohosting a talk show, just so it can be called Burstyn With Flavor—but after Austin, I had my doubts. I’d cracked under pressure once; until I tried again, I’d never know fissure. As it turned out, a second chance was around the corner.

The Bay Area Pun-Off, a monthly philharmonic of harmful phonics. Ryan Young

Compact and jovial, Jonah Spear is a dead ringer for Saturday Night Live’s Taran Killam—or at least for Taran Killam in high school: Spear recently shaved off a grizzled-prospector beard and looks about half of his 34 years. He’s also a professional play facilitator and counselor at an adult summer camp (no to phones and drinking, yes to sing-alongs and bonfires). That loosey-goosey vibe has carried into the Bay Area Pun-Off, a monthly event Spear began hosting in January that’s just one of a handful of competitive punning events popping up across the country.

If the O. Henry Pun-Off is the Newport Folk Festival, then its Bay Area cousin—like Punderdome 3000 in Brooklyn, Pundamonium in Seattle, or the Great Durham Pun Championship in, well, Durham—is Coachella. The audience is younger, and the raucous atmosphere is fueled as much by beer as by unabashed pun love. It started in the living room of a communal house in Oakland in January 2016 but quickly outgrew its confines; in June the organizers even staged a New York City satellite event.

But on this Saturday night, a week after O. Henry, it’s a high-ceilinged performance space in San Francisco’s Mission District where I’m looking for redemption. The pool of contestants at the Bay Area Pun-Off is small by O. Henry standards, and we commence with an all-hands marathon on tree puns designed to winnow the field of 12 down to eight. “I’m just hoping to win the poplar vote,” one woman says. “Sounds like birch of contract to me,” says someone else. A lanky British guy whom I’ll call Chet rambles through a shaggy-dog story involving a French woman and three Jamaican guys to get to a tortured “le mon t’ree” punch line. The crowd eats it up.

"Keep the applause going. It takes balsa get up here and do this."

When you’re waiting for 11 other people to pun, you’ve got plenty of time to think of your next one, so I try to Ziek out a good-sized reserve of puns—and when it’s my turn, I make sure that my puns build on the joke that came before me. “Keep the applause going,” I say after someone boughs out. “It takes balsa get up here and do this.” After someone delivers a good line, I admit that “I ended up being pretty frond of it.” They’re not distinctive, but at this stage they don’t need to be, as long as they’re ambiguous. Things go oak-ay, and I’m on to the next round. (What, yew don’t believe me? Olive got is my word.)

After I indulge in a muggleful of Harry Potter puns, I find myself in the semifinals against a Quora engineer named Asa. Spear scribbles the mystery topic on a small chalkboard hidden from sight, then turns it around. It says … diseases. The same category that knocked me out in Austin? The category I dwelled on for the entire flight home, thinking of all the one-liners that had eluded me?

This time, there’s no running dry. Not only do I remember all the puns I used against Ben Ziek, but I remember all the puns he made against me. So when Asa says, “I’m really taking my mumps,” I shoot back with “That’s kinda measly, if you ask me.” I reprise puns I’d made in Austin (“Did you see that Italian opera singer run through the door? In flew Enzo!”); I use puns that I’d thought of since (“My mom makes the best onion dip. It’s HIV little concoction you’d love”). Asa fights gamely, but I have immunerable disease puns at my fingertips, and it’s not much longer before the round is over.

And then, again, there are two: me and Chet. The difference now is I’m locked in: no nerves, no self-consciousness, just getting out of my brain’s way and letting the connections happen. When Spear announces the theme—living world leaders—I don’t even start trying to stockpile puns. I just wait, and they come.

Chet opens the round: “Ohhhh, BAMA. I don’t know anything about world leaders!”

This time, just hearing him mention Obama conjures up a mental image of Justin Trudeau. Before the laughter even dies down, I nod my head encouragingly: “True, tho—that was a decent pun!”

It’s Austin all over again, just in reverse: Now I’m the quick one and Chet’s the one who has to scramble. He fumbles through a long story about rock climbing that leads to a pun about his cam-bell. (And before you ask: Chances are he wasn’t actually talking about Kim Campbell, who was prime minister of Canada for all of six months in 1993, but in the heat of the moment no one realized he’d just screwed up David Cameron’s name.)

My turn? No problem. Just keep flipping it back to him. “Another patented long-ass Chet story,” I say. “I am Bushed.”

“Well,” Chet says, then pauses. “He thinks he can just … Blair shit out.”

It’s his one solid blow. I talk about the “bonky moon” that’s shining outside that night. I confide in the audience about my own alopecia problem, and how I needed to buy a Merkel. And each time, the audience is right there with me. They don’t necessarily know what’s coming, but they’re loving it. Chet’s used three US presidents and two prime ministers; meanwhile, I’ve been from South Korea to Germany, by way of Canada.

Even better, I’ve got another continent in my pocket. “Have you guys been to Chet’s farm?” I ask the audience. “He has this group of cows that won’t stop talking.” I wait a beat. “They are seriously moo-gabby.”

What happens next is a blur, to be perfectly honest. I can’t even tell you what comes out of Chet’s mouth next, but it’s either nothing or it’s the name of someone dead—and either way, the Bay Area Pun-Off is over.

I might not have been able to vanquish Ben Ziek; this may be my only taste of victory in the world of competitive paronomasiacs; hell, I may never know the secret to the perfect pun. But as long as I’ve got the words to try, one thing’s for sure: I’ll use vaguely different words to approximate those words, thereby creating incongruity and thus humor.

Or maybe I’ll just plead raita’s block.

Author Peter Rubin set up a Slack channel here at Wired to crowdsource the punny headlines for the opening illustration to this story. He compiled more than 150 of them. Here are the ones we couldn’t fit.

1. PRESENTS OF MIND

2. SHEER PUNDEMONIUM

3. VIRULENT HOMOPHONIA

4. OFF-SYLLABLE USE

5. PUNBELIEVABLE

6. HEADLINE BLING

7. LIVE A CRITIC, DIACRITIC

8. FEAST OF THE PRONUNCIATION

9. VERBAL MEDICATION

10. THE BEST OF BOTH WORDS

11. SUFFERING FROM INCONSONANT

12. DAMNED WITH FAINT PHRASE

13. THE SEVEN DEADLY SYNTAXES

14. THE NOUN JEWELS

15. PUN’S THE WORD

16. CONSONANT READER

17. FARTS OF SPEECH

18. PUN-CHEWATION

19. GRAMMAR RULES

20. POISSON PEN

21. PUNS AND NEEDLES

22. DEATH AND SYNTAXES

23. THE WRITE STUFF

24. MAKING THE COPY

25. SLAIN LETTERING

26. PUN AND GAMES

27. VALLEY OF THE LOLZ

28. NOUN HEAR THIS

29. WHATEVER FLOATS YOUR QUOTE

30. PUT A VERB ON IT!

31. CRIME AND PUN-NICHE-MEANT

32. TIC TALK

33. ECCE HOMONYM

34. DEEP IN THE HEART OF TEXT’S ASS

35. WRITES OF MAN

36. VERB APPEAL

37. THE RHYME DIRECTIVE

38. SLOGAN'S RUN

39. REBEL WITHOUT A CLAUSE

40. BURNS OF PHRASE

41. ARTLESS QUOTATIONS

42. BON MOT MONEY, BON MOT PROBLEMS

43. JESTIN' CASE

44. LET 'ER QUIP

45. ADVERB REACTIONS

46. INFINITE JESTS

47. ARTS OF SPEECH

48. DIGITAL PUNDERGROUND

49. THE PUN-ISHER

50. IMPUNDING DOOM

51. BEYOND PUNDERDOME

52. BAUHAUS OF CARDS

53. TEXTUAL HARASSMENT

54. IT'S A PUNGLE OUT THERE

55. GRAND THEFT MOTTO

56. IT HAD PUNNED ONE NIGHT

57. PLEASE GRAMMAR DON'T HURT ’EM

58. RHETORICAL QUESTIN'

59. ACUTE PUNS? SURE

60. BAWDILY HUMORED

61. DAMNED IF YOU INNUENDO, DAMNED IF YOU INNUENDON'T

62. TROUBLE ENTENDRES

63. WITS UP, DOC

64. SELF-IMPROV MEANT

65. PUN-EYED JOKERS

66. LAUGHTERMATH

67. JAPES OF WRATH

68. MAKING HA-HAJJ

69. MUTTER, MAY I?

70. BATTLE OF HALF-WITS

71. DEMI-BRAVADO

72. MALCONTENT MARKETING

73. NON-SILENT OFFENSES

74. ORAL HIJINX

75. THE PUN-ISHER

76. NOUNS, YOUR CHANCE

77. TEXT OF KIN

78. OH, PUN AND SHUT

79. JOKE OF ALL TRADES

80. PATTER UP

81. SCHTICK IT TO ’EM

82. BOOS HOUNDS

83. IT'S NOT EASY BEING GROANED

84. FAR FROM THE MADDENED CROWD

85. COMPETITIVE DEBASING

86. THE PUNFORGIVEN

87. THE PUNCANNY VALLEY

88. INTENTIONAL FORTITUDE

89. CHURCH OF THE LETTER DISDAIN

90. POETRY IN MASHIN'

91. CREATIVE SENTENCING

92. DAAAMN, DACTYL!

93. NO CONTEXT

94. A TALE OF TWO SILLIES

95. THE WIZARD OF LOLZ

96. IT'S A PUNDERFUL LIFE

97. WHAT'S HA? PUNNIN'

98. THE ZING AND I

99. THE WILD PUNS

100. THE PUN ALSO RISES

101. HOW THE REST WERE PUNNED

102. RAGING SYLLABLE

103. DANGEROUS ELISIONS

104. GOODWILL PUNTING

105. FELLOWSHIP OF THE WRONG

106. INGLOURIOUS LAST WORDS

107. THE LIMITATION GAME

108. APPETITE FOR DISTRACTION

109. HOW I MEANT ANOTHER

110. LARKS AND RECREATION

111. COMEDY OF AIRERS

112. DECLARATION OF INNER PENANCE

113. BOO HA-HA

Senior editor and pun criminal Peter Rubin (@provenself) wrote about the roadblocks to VR in issue 24.04.

This article appears in the October 2016 issue.