When Henry Hook was fourteen years old, living in East Rutherford, New Jersey, his grandmother gave him a crossword jigsaw puzzle for Christmas. Designed by Eugene T. Maleska, who became a legendary editor of the Times crossword, the puzzle had three parts. First, you had to solve the crossword puzzle on paper; then you had to fit the jigsaw pieces together in order to verify your answers. When you were done, if you looked carefully you could find a secret message zigzagging through the answers: “YOU HAVE JUST FINISHED THE WORLD’S MOST REMARKABLE CROSSWORD.” Hook was less than impressed. Within a matter of days, he sent a rebuttal puzzle to Maleska. It contained a hidden message of its own: “⁠WHAT MAKES YOU THINK YOUR PUZZLE IS MORE REMARKABLE THAN MINE?”

In the thirty-two years since then, Hook has come to be known as the Marquis de Sade of the puzzle world: a brilliant and oddly beloved misanthrope, administering exquisite torture through dozens of puzzle books and syndicated crosswords. But he’s not used to being clueless himself. Standing at the corner of Forty-third Street and Ninth Avenue one Saturday night, glaring out from beneath a Brooklyn baseball cap, he looks both fearsomely focussed and a little disoriented. He’s been brought here, along with a team of other puzzle experts, by a blank scroll of paper—the first clue in an elaborate treasure hunt known as Midnight Madness. From Fortieth Street to Sixtieth Street and from the East River to the Hudson, fifteen teams are scrambling across Manhattan in search of clues, each of which points to another location. Every fifteen minutes, teams can call in to headquarters and ask for a hint; the first team to reach the last location wins.

Half an hour ago, one of Hook’s seven teammates pulled out a tape measure and found that the blank scroll was exactly forty-three by nine inches. That brought them to this intersection, where they’ve been searching ever since. Across the street, a writer for “Who Wants to Be a Millionaire” and a crossword virtuoso named Ellen Ripstein are scrutinizing graffiti in a phone booth. Catercornered to them, the editor of the Wall Street Journal crossword is standing beside a professional palindromist who is riffling through a bin of adult-education pamphlets. But by now they’re not alone. All around them, spindly cryptologists from fourteen other teams are scanning signs and peering sharply at Chinese menus. Hook’s teammates already look winded—they’re accustomed to more sedentary puzzle-solving—but their opponents are dismayingly sprightly. They are also better prepared: one team has come with nearly twenty members, many of them dressed in black, who are being deployed like ninjas around the intersection.

Hunts like this are the X-Games of cryptology: half wordplay and half extreme sport. The clues are as much as a mile apart, and the organizers—three shadowy figures known to us only by their first names—seem more interested in absurdist humor and elaborate effects than in pure deductive logic. “I hope you know I’m missing my karaoke night for this,” Hook mutters, lumbering past. Given his reclusive ways, it’s a wonder he agreed to join at all, and it’s clear that he expects to regret it. The T-shirt he’s wearing shows a man with thick spectacles irately crumpling an I.Q. test. “Why am I doing this?” the man is saying. “Why am I allowing myself to be humiliated by these moronic puzzles?!”

Before long, Hook’s team is so desperate for a clue that the writer for “Who Wants to Be a Millionaire” begins quizzing a local panhandler and calling in random guesses to headquarters. Finally, during one call, someone tosses him a lifeline: “Fearless, brave, bold, courageous, valiant, heroic, daring, resolute, audacious, plucky.” The puzzlers glance up at one another with twisted grins: at long last, some words. Then they charge off, as one, for the Hudson.

I first met Hook at the 2001 American Crossword Puzzle Tournament, in Stamford, Connecticut, the largest gathering of puzzlers in the world. (This year is the twenty-fifth anniversary of the event, which will be held from March 15th through the 17th.) More than fifty million Americans solve a crossword at least occasionally, making this by some accounts the most popular indoor pastime in the country. Of these, an élite three hundred and fifty or so come to Stamford every year. In the lobby of the local Marriott, you can see them slumped in armchairs and hunched over coffee tables, playing newly invented board games and odd variations on charades. In the hallways, venders peddle puzzle books, crossword art, and a custom-made crossword Barbie, complete with miniature clue sheets, grids, and pencils. When one puzzler saw me wandering around a little befuddled, he swept his arm across the room as if he were a ringmaster: “Welcome to Weirdoland!”

Joshua Kosman, a classical-music critic for the San Francisco Chronicle, is a typical attendee. “The past fifteen years, for me, has been a process of sinking into, codifying, and coming to terms with the fact that this is what I do. That I’m a puzzle guy,” he told me. Then he cut to the chase: “Did you know that Britney Spears has signed a big endorsement deal with Pepsi? That’s right, it’s true, and we are all very happy about it. You see, ‘Pepsi-Cola’ is an anagram of ‘Episcopal’ and ‘Britney Spears’ is an anagram of ‘Presbyterians.’ ” He paused to let this sink in, but my reaction wasn’t quite what he had hoped for. “Yeah, I know,” he said. “ ‘Episcopal’ is singular, and ‘Presbyterians’ is plural. But we take what we can get.”

For nearly a hundred and twenty years, people blessed with such minds have found one another through the National Puzzlers’ League, which publishes a monthly newsletter called The Enigma. The three hundred and fifty-odd members of the league go by code names that are themselves often miniature puzzles: Kosman’s is Trazom (Mozart backward); a member named Ilene goes simply by I, because the italics make the “I” lean. Over time, the league’s ranks have fissured into the usual sects and denominations: rhyming riddlers, acrostic enigmatologists, and the like. But crosswords are the common denominator, and in Stamford the participants are sorted into a single, ruthless hierarchy.

It wasn’t always so. Not long after crosswords were invented, by an editor at the New York Sunday World, in 1913, The Enigma called for an “anti-toxin to prevent people from taking this dread disease.” The new puzzles were an “inane mental exercise”—glorified quiz sheets for woolly-headed dictionary lovers. But, with time, crosswords grew more intricate and demanding, and puzzlers now reserve their contempt for Scrabble fanatics. Competitive Scrabble is all about memorizing lists of two-, three-, and four-letter words, puzzlers say. But rote memorization won’t help you in Stamford. There, everyone sits at cafeteria-style tables in the ballroom, filling in grids while a giant clock ticks away onstage. Invariably, the same hands dart up first, followed, at predictable intervals, by batches of also-rans and then the rest of the rumbling herd. “I’ve done over nine hundred crosswords in the past three months to get ready for this,” a kindly, silver-haired puzzler from Pennsylvania named Carolyn Bartlebaugh told me. “I’ve just saturated my brain with two-toed sloths and so forth.” But she didn’t expect to gain much ground. “If I can crack the top hundred, I’ll be happy,” she said.

To shave seconds off their response times, some puzzlers learn to read clues and write answers simultaneously, to scrawl their “e”s with a single stroke, and to start with the easy, fill-in-the-blank questions. But real success depends on qualities that aren’t so readily learned: instant recall, omnivorous interests, a genius for pattern recognition, and a certain, double-jointed wit. During the past fourteen years, the same four players—Trip Payne, Douglas Hoylman, Ellen Ripstein, and Jon Delfin—have claimed thirty-six of the tournament’s forty-two spots for finalists. This year, as usual, all four were competing.

Sitting in the ballroom on the first morning of the tournament, I watched Payne, a gangly two-time champion from Georgia, limber up with the Saturday Times crossword. The Times edits its puzzles to get harder as the week progresses: an average solver will do the Monday puzzle in an hour or so, the Wednesday in two hours, and fling the Saturday puzzle across the room in a fit of impotent fury. But Payne didn’t look worried. Flipping to the puzzle, he punched a stopwatch, cast his large, liquid eyes over the clues, and began to scribble. And never stopped. “Halberdier’s opponent”? “Lancer,” of course. “Resistance figure”? What else but “ohmage”? When the last square had been filled, Payne shouted “Done!” and slapped down his pencil. The stopwatch read 7:27.

A few tables away, Ellen Ripstein was carefully arranging her papers and pencils on the table. At forty-eight, she still looked like a schoolgirl, with her round, guileless face, toothy smile, and Orphan Annie dress. She made her living as a researcher for a game show (she wasn’t allowed to say which one), and had spent the past few weeks solving ten to fifteen puzzles a day under tournament conditions. At one point, she completed a Saturday Times puzzle in 4:46, yet she knew that speed wasn’t enough. In 1988, she finished first in the finals, only to find that she had made one error: she’d written “senseleseness” instead of “senselessness.” Since then, she had extended her streak of top-five finishes to eighteen years—an astonishing run—without once winning. She was known as the Susan Lucci of crosswords.

Twelfth Avenue and Forty-sixth Street, Pier 86, 9:15 P.M.

The U.S.S. Intrepid hasn’t seen action since Vietnam, but, rising from the Hudson in great gray battlements, its searchlights probing the underbellies of clouds, it still looks plenty fearless, brave, bold, courageous, valiant, heroic, daring, resolute, audacious, and plucky. Along the pier, players from various teams aim their flashlight beams across the water’s oily surface, picking out pop bottles, decayed life preservers, scraps of billboard, and a broken doll stranded on the pilings. It’s tempting to climb down for a closer look—there could be a recording in the doll’s head—but just then the palindromist comes running up. “I found this hidden beside that tank, over in front of the ship,” he says, catching his breath. He’s holding a large manila envelope.

Inside is a gray postcard with a picture of Joe DiMaggio. “Notice anything odd about it?” the palindromist says, grinning. The puzzlers pass the postcard around, flip it over, and squint at the photograph. Nothing. Then they feel it: the faintest buzzing at their fingertips. Sandwiched somewhere inside the cardboard is a tiny speaker, and it’s playing the next clue. When they lift the card to their ears, the vibration swells into a sound, a rhythm, and then a syncopated tune: “Her name was Lola, she was a showgirl . . .”

The reigning king of puzzledom in Stamford—the seemingly immovable object through which Ripstein had to pass—was Douglas Hoylman, a retired insurance actuary, also known as the Ice Man. Hoylman is a pale, blinking hulk of a man, so shy and deliberate as to seem almost slow-witted. Yet he has a Ph.D. in mathematics (his dissertation solved an old conundrum concerning the optimal packing of tetrahedrons) and a memory that stretches, flawlessly, from Harry Truman to “The Truman Show.” By the time I met him, he had won the tournament six times—a record—including three out of the previous five years. I was startled to find, therefore, that the puzzle hierarchy didn’t end with him. “I’ve timed myself against Stan Newman, and he’s much faster than I am,” Hoylman said, referring to a former champion who holds the official record for solving the Monday Times crossword—2:14. “And if David Rosen were still in the tournament he’d probably still be winning.”

The true élite, it turned out, tend to bow out of competition. They serve as officials, or construct crosswords for the tournament, and leave the prizes to others. I found them later that morning, sprawled in a conference room on the second floor, eating Irish soda bread and washing it down with a growler of home-brewed Crossword beer. Rosen, tall and bald, with lively eyes behind brown horn-rimmed glasses, was sitting beside Maura B. Jacobson, the elfin editor of the New York magazine crossword. As referees brought in completed puzzles, Rosen and the other twenty or so officials scored the answers, pausing only to ridicule the occasional hapless entry.

“Who the hell writes ‘skua’ with a ‘q’?”

“Eriq LaSalle!”

“Wasn’t he just on the cover of GQ?”

“You mean GK.”

Halfway through a particularly inept puzzle, Rosen’s red pen suddenly stopped moving. “For the ‘God of sex,’ this one answered ‘Iris,’ ” he said, smiling wistfully. “Who knows? Maybe she is.”

Rosen, who designs voice-response software for a living, is the subject of what is perhaps the most famous legend in the puzzle world. Several years ago, he beat an accomplished crossword constructor named Peter Gordon in an informal race, even though Gordon was filling out his own puzzle. The next year, they tried it again, but this time Gordon went over the puzzle the night before. He still lost.

In his heyday, Rosen usually beat Stan Newman, the other former phenomenon, so it seemed safe to say that he was the fastest solver around. But, as we were talking, bursts of laughter kept interrupting us from another table. Glancing over, I recognized a brassy brunette named Nancy Schuster, who won the first Stamford tournament, in 1978. Most of the jokes, though, seemed to be coming from the judge beside her. He was dressed like a banker from the waist down—black slacks, navy-blue socks, polished loafers—and like a Beastie Boy from the waist up. A baseball cap was jammed over his fringe of gray curls, and a very large logo covered his ample upper body: “DID YOU EVER STOP TO THINK AND FORGET TO START AGAIN?” With his bulbous features and his weed-whacker voice, he reminded me a little of W. C. Fields and a little of the singing frog from the old Warner Bros. cartoon: hogging the spotlight even as he hid from it.

Rosen swivelled around to follow the commotion, then turned back to our table. When I asked him who the guy in the T-shirt was, he grinned. “That’s the man you’re looking for,” he said. “He’s in a class by himself.”

The man, of course, was Henry Hook.

Fifty-seventh Street, between Eleventh and Twelfth Avenues, 10:30 P.M.

Under the neon lights of the Copacabana, among the Kahlúa-skinned women in salsa dresses, a man with fifteen white balloons is talking to the writer for “Who Wants to Be a Millionaire.” The writer nods, takes one of the balloons, and stomps on it. A translucent scroll falls to the pavement. Unfurled, it shows a small clock with hands pointing to seven-forty-two, and a keyboard without letters. A series of numbers, from one to twenty-one, are scattered across the keys.

“Here, let me do this,” Ripstein says. “I type over a hundred words a minute.” While the others hold the scroll against a brick wall, she positions her fingers on the imaginary keys. She looks to see which letters the numbers correspond to, then calls them out in sequence. But she keeps getting flustered and losing her place. Hook finally steps in. “I don’t see why you’re bothering with that,” he says. “I’ve got the letters memorized: Q W E R T Y U I O P A S D F G H . . .” Less than a minute later, they have the clue: cat.nyu.edu/rebecca/m. Then they hop into a cab and send the driver to Seventh Avenue and Forty-second Street, in search of a computer.

The urge to play with words tends to possess puzzlers early. Ripstein filled out her first children’s crossword by the age of six and soon graduated to her parents’ grids. Hook started even younger, linking and anagramming letter blocks on his bedroom floor at the age of four. From the start, he was a puzzle polymath, able to solve and construct both word and number puzzles with blinding speed. “It’s like he has ten pencils for fingers,” Nancy Schuster told me. “If he were a rocket scientist, we would probably be on Mars by now.”

Not long after Hook sent Eugene Maleska his rebuttal puzzle, Maleska wrote him a letter. “He thought I was in the business,” Hook recalls. “But I was just in high school.” The two struck up a correspondence, and Maleska eventually invited Hook to his house for some pointers. It’s hard to imagine a meeting of less compatible minds. Maleska had taught Latin and English and worked as a school superintendent, and he brought the same knuckle-rapping rigor to editing puzzles. His grids were scrubbed free of brand names and vulgar trivia. They were larded with famous operatic sopranos, laced tight with obscure Central Asian rivers, and stuffed with crosswordese (words like “esne”—an Anglo-Saxon slave—which seem to survive only in crosswords). Although Maleska spent his life creating games, he was an educator first and an entertainer second.