New Yorker Article, Feb. 2002

The Riddler

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: QWERTYUIOPASDFGH..." 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.

Hook was neither. "I got into this business to torment people," he says. "On that line on the tax form where they ask for your occupation, I'd like to put 'Grand Inquisitor.' " Latin and Greek were of limited interest to him, but he loved the indeterminacy of language — the way "Rapunzel" could be defined as "She was stuck up" — and the smudgy double meanings lurking in syntax. He was a glutton for game shows, a student of slang and shifting idioms, and a dedicated follower of pop celebrities. If Maleska was a classicist, Hook was a puzzle postmodernist.

Still, at first Hook could hardly afford to rebel. His father died when he was seventeen, leaving him with his mother to support, and though he earned a degree in mathematics, he never seriously considered using it. For years, he spent his nights constructing puzzles at fifty dollars each and his days unloading trucks at the back of a drugstore. ("I held a variety of jobs," he once wrote, "all of which have served as excellent training for my current position, which is usually at a forty-five-degree angle, facing southwest.") Finally, in 1980, at the age of twenty-four, Hook joined the staff of the magazine Games — and proceeded to yank crosswords out of the schoolroom at last.

Games was the country's first self-respecting puzzle publication: a thick glossy in a genre long dominated by fly-by-night newsletters. Soon after its founding, in 1977, its circulation rose to two hundred thousand and a clutch of brilliant constructors left their monastic cells to join it. Their strategy was simple but revolutionary: instead of offering straightforward clues to obscure words, they would offer clever clues to common words. (When Hook stooped to using "esne," he clued it as "A slave to crosswords.") Instead of rigidly quoting the dictionary, they would stretch the boundaries of language. In a puzzle called "Element 18," for instance, Hook removed the letter "R" from all the answers — element eighteen in the periodic table being argon.

Maleska, by then, was ensconced in his mountain fastness at the Times, spraying buckshot at the growing horde of mutinous phrases below. He rejected one constructor's puzzle because it contained "car seat," and another because it contained "air play"; in both cases he assumed that the phrase was made up. "I still have some of his letters around," one constructor told me. "They were usually along the lines of 'Get out of the business. Never make a puzzle again.'"

There was a point during those years when it seemed as if Hook might learn to love his fractious place in the puzzle world. The Games constructors eventually carried the day, freeing up the puzzle vocabulary, if only a little ("bra" might now be clued as "Shape shifter," but "Two cupfuls of milk" would still be rejected). Then, in 1984, at a party for puzzlers, Hook met a woman named Stephanie Abrams and instantly, improbably, fell in love. "I was astonished that he could find someone," Schuster told me. "But Stephanie was a very clever puzzler, and she brought out a whole side of him that was hidden." Within a year, Hook moved to Massachusetts to join her, and the two were married. She began to construct crosswords and word-search puzzles, with the help of her live-in editor, and helped put together a puzzlers' convention. But Abrams had cystic fibrosis and her condition worsened month by month. Only four years after they met, she died. "I stayed there another year," Hook says, "and then I had to get away."

He lives and works in Brooklyn now, not far from Prospect Park, in a small wooden house so barricaded to guests that he barely lets the cable man in. "I'm the guy that inspired the phrase 'Doesn't play well with others,' " he says. On most days, he wakes up by seven, does a word search to get his eyes focussed, and then spends the day shuttling between his crossword grids, his reference books, and the television. More and more crossword constructors are relying on computer programs and data bases of common clues. Hook uses only a pencil ("A computer looks really stupid tucked behind your ear"), yet he has been known to come up with twenty-four crosswords and write more than fifteen hundred clues in three days. In addition to constructing a crossword for the Sunday Boston Globe every other week, he writes two puzzle books a year for Random House and hundreds of puzzles that are syndicated for smaller publications.

Then again, there is very little to distract him. Once a week, Hook used to get dressed up, walk to a karaoke bar several blocks away, and belt out a few Sinatra or Elvis tunes. But, he says, he got bored with the same old crowd, and he gave up his membership in the National Puzzlers' League long ago — "logophilia in the extreme." He says he dreams of being a former crossword constructor, but it's not clear what else he would do. A while back, Schuster went to visit him in Brooklyn. "When someone has so many virtues, you forgive him his eccentricities," she says. They met for lunch, went to the park, and played Scrabble. And then Schuster went home.

Fifty-third Street, between Fifth and Madison Avenues, 12:01 A.M.

A light rain is falling on the East Side, glazing its abandoned streets in silver. Hook's team wanders through, trading puns and trying to think of rhymes for "borscht." An hour ago, the clue from the Copacabana led to an Internet café in Times Square, where an intricate online scavenger hunt eventually coughed up this address: "53RD NAHE FÜNF." Now one of Hook's teammates ducks into the portico of the Rolex Building and looks around expectantly. "Nahe Fünf, nahe Fünf," he says. "The hiding place has to be Germanic."

But the portico is empty. As everyone scatters to search the rest of the block, two members of the black team wander past, already headed for the next clue. It takes Hook's team another ten minutes to find what they're looking for: a large Ziploc bag hidden behind a slab of the Berlin Wall. Inside the bag is a page of rubbings taken from a sequence of small bronze reliefs of New York landmarks; one of the landmarks is conspicuously missing. "I've seen those near Grand Central," the Wall Street Journal's crossword editor says. Then he beckons the others back into the rain.

On the last day of the Stamford tournament, it was breezy and the sky was breathtakingly blue, though few of the puzzlers noticed. After a long Saturday of competition, they had stayed up until 4 or 5 A.M. playing games. I found them late in the morning, clustered around a wall beside the check-in desk, craning their necks to see the final standings. Carolyn Bartlebaugh, the puzzler from Pennsylvania, was thrilled; after six puzzles, she was ranked at exactly a hundred. But the top of the hierarchy had been shockingly rearranged. Trip Payne, after loping to his usual lead, had somehow blanked on celebrity bullfighters and written "Masolete" instead of "Manolete," and Douglas Hoylman, the Ice Man, had been just a little too methodical: he was in fourth place, six minutes short of qualifying for the final. The only familiar face in the finals was the most familiar one of all: Ellen Ripstein had extended her streak to nineteen years, matching Susan Lucci's nineteen nominations before she won an Emmy.

In the afternoon, three giant crossword grids were set on easels at the front of the ballroom, and the finalists took their places holding erasable markers. To the left was Al Sanders, a perennial also-ran from Colorado. (On the first day, I'd heard someone mutter, in mock indignation, "Why is it I get the impression that no one is taking Al Sanders seriously?" Everyone had burst out laughing, yet here was Sanders.) Beside him was Patrick Jordan, a solver from Oklahoma who had worn a bright-green stovepipe hat throughout the early rounds. Ripstein was on the far right, looking too short to reach the top row of the puzzle and surrounded by cameramen from ABC and CBS. To drown out any hints or distractions, the finalists were wearing headsets that played crowd noise recorded at the United Nations.

Back in the nineteen-twenties, such hoopla might not have seemed so anomalous. The first book of crosswords, published in 1924 by Dick Simon and Max Schuster, sparked a nationwide craze and launched the publishing firm of Simon & Schuster. But when I spoke to Will Shortz, the current Times crossword editor, he was anything but nostalgic. Shortz is the only person in the world who has a degree in enigmatology (he designed his own course of study at Indiana University), so he knows crossword history. "We are living in the golden age of puzzles," he said. Constructors now achieve the most dazzling architectural feats routinely, laying down triple rows of fifteen-letter answers twice or even three times in a single puzzle, and weaving clever themes through their grids like morning glories. In the process, they're winning over a new generation of solvers. Earlier that week, Shortz had told the Wall Street Journal that the crowd would "blow the roof off the hotel" if Ripstein won. In reply, the Marriott management had greeted Ripstein with a fruit basket and a welcome letter. "Best of luck this weekend," it said. "We will have the roofers stand by."

The only person who seemed not to be primed for cruciverbalist rapture was Hook: as usual, he had slipped off before the final round. Twenty years earlier, at an élite crossword tournament in Ridgewood, New Jersey, he was given four formidable puzzles to solve, a time limit of close to three hours, and a chance at a grand-prize trip to England. He finished in half an hour ("I hate to tell you this," the m.c. announced, "but you're all competing for second place"), then spent the rest of the time trading acrostic notes with Nancy Schuster. He never went to England and never entered another tournament. "I'm not a traveller," he told me, and speed-solving felt too much like stenography.

In Stamford, Ripstein got off to an early lead, and managed to dash off "aristas" ("Some beards") and "bhang" ("Hallucinogenic drink made from Indian hemp"). But her strategy was unorthodox. Instead of starting at the upper left corner and working her way around the puzzle, she jumped immediately to the right side. That left her stranded without 1 across ("What sots don't do?"), a ten-letter answer on which much depended. Jordan took the standard path, built on previously placed letters, and soon surged ahead. He filled in "at bats" ("Denominator in some stats") and "coigns" ("Wedge-shaped pieces of wood"), and hesitated only briefly before writing "bard" ("Avon calling?"). When he bent down to fill in the final square, to a scattering of applause, all the air seemed to go out of the room. Even without the Ice Man around, Ripstein couldn't win.

Or could she? A murmur of protest rippled across the ballroom. At the lower right corner of the puzzle, in response to "Bonaventure, e.g.," Jordan had written "past" instead of "mast." Like Ripstein in 1988, he had made a single, senseless error.

Afterward, when Ripstein had finally figured out what sots don't do ("pass the bar") and Al Sanders had limped in for a distant third, the crowd erupted almost as explosively as had been predicted. The TV cameramen raced down the aisles for startling closeups of unusual words (it's hard to make a puzzle seem dramatic), and Ripstein took off her headphones so that she could, at last, hear her acclaim. "Is that your lucky dress?" a reporter shouted. "How did you prepare?" Ripstein smiled, her face incandescent above the cloud of reporters and klieg lights. Then she calmly gave the answers that she'd been preparing for nineteen years.

Corner of Mercer Street and Waverly Place, 2 A.M.

The victory party has already begun. Along the bar and in the booths of a subterranean college dive, members of the black team are downing beers and smiling smugly at more recent arrivals. When the jukebox plays ABBA's "Dancing Queen," they leap from their seats with a whoop and shout for more volume, then flail around like pieces of squid-ink pasta.

One by one, Hook's teammates shuffle in, looking more disoriented than ever. For a short while, at the Internet café, they seemed to be in the lead. But a stalled subway car cost them half an hour, and the clues that followed were so simple that they couldn't catch up. The missing landmark from the page of rubbings was Lever House, a modernist skyscraper at Fifty-third Street and Park Avenue. There, a man in a white lab coat gave them one plastic vial with five units of water and another vial with one unit — a clear reference to Fifty-first Street, along the river. The hunt came to an end on a footbridge above the F.D.R. Drive, where a series of digits, illuminated by glow sticks, spelled out a cell-phone number. When they made the call, they were given this address, and were told they had finished in second place.

"I hope the balloon guy is here," Hook says. "I'd really like to see him again." But the costumes have all been put away, and with them the air of mystery that seemed, for a time, to suffuse the city. Hook shifts and fidgets, looking suddenly a little old to be wearing a puzzle T-shirt. He sips his Coke a bit too fast and edges toward the exit, as the dancers pogo around him. Then he notices something. Sitting on a stool near the door, keeping a mildly menacing eye on the crowd, is a bald, muscle-bound bouncer. In his lap is a copy of the Times Sunday crossword, half solved.

For every Midnight Madness player or crossword competitor, there will always be a hundred thousand others like this, scribbling on subways, in private studies, and in the back booths of anonymous diners, nursing their obsessions in secret. "No one ever talks about them, but we know they're out there," an editor in Stamford told me. "Every time a newspaper changes its puzzle format, the switchboard lights up." When the other puzzlers see what Hook sees, they grin and lean over to find out who constructed the puzzle. The jukebox switches to Tom Jones belting out "It's Not Unusual," and soon the enormous bouncer is being introduced to the diminutive national crossword champion. "I usually do the Monday and Tuesday," he tells her bashfully, covering his answers with his hand. "But Wednesday and Thursday are a little too hard." Ripstein nods and smiles, as if she knows exactly what he means.

Crosswords aren't so different from life, one constructor told me. You start out floundering in a void, plagued by questions. And then, little by little, you begin to find answers. You build gradually on your knowledge, or make mistakes and double back, and pretty soon you find that everything is connected to everything else. But if crosswords can be addictive — if some people love them nearly to the point of folly — it may be because real life hardly enters into them. Here every problem has a solution, and pain, disease, violence, and despair never make it to the grid. "When you solve a crossword, you don't want death or Nazis thrown in your face," Will Shortz says. "If there is a seventy-year-old woman who is filling out the grid and she's got '__uck,' I can't imagine making her add an 'F.' "

Hook can. His career has been one long effort to subvert our safe assumptions about puzzles, to make them as unsettling and unpredictable as art. On the cab ride back to Brooklyn, he reminds me, for the third time, never to let him join another treasure hunt. But then he seems to have second thoughts. "I've been thinking that you could make the whole thing a lot nastier," he says, as he's getting out. "Wherever there is a clue, there could be a sign nearby. Every sign would have a letter missing, so for the last clue you'd have to take those missing letters...." And with that he wanders off into the Brooklyn night, alone once again. The avenue is deserted, and the traffic lights and neon signs flash for no one. But, to Hook, every glowing word has a life of its own. As he walks past, the letters seem to break ranks and crowd together above his head; they shift and shuffle, leap and double, pair up and trade partners like a chorus line at the Copacabana. Then they quietly assume their places again, and await the next puzzler.