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The first crossword puzzle was created by a journalist named Arthur Wynne on Dec. 21, 1913. It appeared in the New York World.

The word "FUN" looms large at the top of the first crossword that appeared out of nowhere on Dec. 21, 1913 – luring in people who should have known better than to put their trust in a three-letter word for simple amusement.The crossword has since occupied a century's worth of brainpower, and it wouldn't have lasted so long if it didn't caress the minds it simultaneously toys with. But "FUN" falls short of describing the fundamental battle of wits designed to show us up, steer us wrong and make us feel good in the end. Extreme pleasure is more like it.

"For me, the dopamine hit comes when a clue that looks utterly baffling turns out to be entirely fair," says Alan Connor, a screenwriter and author of a wide-ranging history of the cryptic crossword, Two Girls, One on Each Knee (i.e. PAT on ELLA).

"The answer has been staring you in the face, and then the penny drops – 'spelling' refers to witchcraft, not the thing you do with words. You're suddenly in a completely different part of your brain, and the leap between apparently unconnected things becomes physically pleasurable."

Today, millions of people around the world solve crossword puzzles every day. No newspaper is complete without one version or another. Scientists believe that the high-level stimulation crosswords provide connects with the brain's survival strategies and links back to the ancient riddles of oracles and sphinxes. Modern puzzles have opened up this enigmatic pleasure, democratizing the challenge by filling clues with topical cultural references, from the Kardashians to indie music, that breathe new life into the old form.

"The crossword puzzle is ever-present in North American and British culture over the last 100 years," says Mr. Connor, who blogs on crosswords for The Guardian. "The story of the puzzle, as it's subtly changed and found different forms, is not that eventful – no blood has been shed. But by becoming a part of a newspaper's daily architecture, it starts to mean a lot to people, and they build up strong relationships with the people who write the clues that goes drip-drip-drip for decades. And so the crossword ends up being this wonderful quiet part of the century."

A crossword for everyone

Longevity wasn't the first priority when an English immigrant named Arthur Wynne created his diamond-shaped grid as a space-filler for the Christmas edition of the New York World – he called it a word-cross puzzle, played it straight, and asked his newbie solvers to come up with the three-letter plural of "IS." But Wynne still managed to make word-crossing hard for himself and his readers by forcing letters to fit into both vertical and horizontal answers – a highly demanding framework, subsequently perfected by the geniuses at The New York Times, that in lesser hands can lead to the obscurities and banalities of what 100 years of complainers have learned to call "crosswordese."

Thus, in Wynne's inaugural attempt at gridding the English language, there were two separate clues (a bird; a pigeon) for the same word, DOVE, the vowel-rich NEIF turned out to be a four-letter synonym for fist, and readers who expected to wallow in cruciverbalizing fun could only do so by realizing that the fibre of the gomuti palm had to be the word DOH. Which, as everyone now knows, is actually a Simpsons shout-out, or the sound of moolah in Springfield, or (for the classicists in the crowd) a Homeric oath.

Much has changed over the crossword's 100-year evolution. There was the crazed phase in the 1920s, when crooners sang Crossword Mama, You're Puzzling Me and novelist P.G. Wodehouse could depict his less-than-brilliant characters searching for the name of a three-letter Australian bird that starts with E and ends in U. Some early trend-spotters felt bold enough to predict that, like all mass outbursts, the crossword would fade as fast as it flared, leaving mahjong as the 1920s diversion most likely to endure.

High-minded social arbiters later worried about the proletariat being distracted by "a primitive form of mental exercise" when they should be devoting themselves to good honest toil. But even when the upper classes and superior beings appropriated the new word puzzle, investing it with classical references and knottier clues that made the exercise more sophisticated, the crossword couldn't escape the naysayers – it stood accused of being the escape hatch of the leisured classes, a private club of well-bred language that only the verbally adept could enter.

The democratizing of puzzles over the last generation – in content, though not in degree of difficulty – has blunted that critique, making it easier for crossword fans to wallow in the pleasure of personal cryptology.

"The crossword is the most flexible form of puzzle ever created," says Will Shortz, legendary crossword-puzzle editor for The New York Times, and guest star in a famous episode of The Simpsons that linked directly to the same day's Times puzzle. "So it's natural that it would have thrived. There's a crossword for every type of person – hard and easy, topical and general, large and small. Crosswords embrace everything in life."

The worldwide puzzle market is now vast and caters to every specific taste and talent. The best crossword constructors take pride in their cultural flexibility and willingness to break down the barriers imposed by earlier generations of class-conscious word guardians – somewhere, someone is eagerly filling in the three-letter word for a Kardashian, first letter K.

Older distinctions between the British tradition of hidden-meaning cryptic clues and the more straightforward American definitionals in the Arthur Wynne style now feel like dated cultural stereotypes. The Americans in particular, led by Mr. Shortz at the Times, have become much trickier, both with punning misdirection in the clues and a hidden-letter preoccupation that would challenge the best wartime cryptographers.

"I always try to amaze people," says Mr. Shortz, well aware that amazement at the crossword level depends on some combination of discovery, surprise and newness. "I'm trying to write clues that are novel and interesting, and later in the week" – when the Times puzzle ratchets up its degree of difficulty – "I want clues that will twist your brain in a fresh way."

He had just finished writing a clue about the band Modest Mouse, a pop-music reference that wouldn't have impressed the old-school classicists who found superiority in knowing the names of all nine inspirational Muses from Mount Helicon (but probably still wouldn't have liked the modern five-letter anagram for the lyre-strumming ERATO, "Tore a new one for Virgil").

"If you're a smart person with an engaging mind, you should be aware of everything in the world," says Mr. Shortz, invoking his "crosswords-embrace-life" clause. "That doesn't mean you necessarily listened to Modest Mouse, but you should be aware there's a band with that name."

And if you don't know them, you should be able to make an intelligent guess based on the hints supplied by the crossing words you've discovered – though even Mr. Shortz can emit a hopeless sigh when the unforgiving Times grid requires intersecting answers like PEE DEE (a river in South Carolina) and the rapper T-PAIN. "That's a tough crossing," admits the master of tough.

The best clues, crossword fanatics agree, are those that don't force you to make a wild guess, pore over the dictionary, bother the Internet or phone a money-making 1-900 answer line. One of the favourite clues of all time, for wordies in the know, is "e" – meaning SENSELESSNESS, because SENSE less the letters NESS leaves you with only an E. Less than fair? Maybe, since the clue reveals its intent only in the answer, which does feel kind of senseless, if not pointless. But at their best and most generous, crossword clues can also be simple and beautiful and productive of miniature delight.

"A lot of crossword people think, 'I want my clues to be hard,' " says Fraser Simpson, a Toronto math teacher who constructs The Globe and Mail's cryptic, a puzzle couched in layers of syntactic playfulness. "But I don't care if they're hard. I want my clues to be elegant, and every once in a while they're going to be hard anyway."

Mr. Simpson is a champion of the kind of misdirection that is both unexpected and clear. As a mathematician, he says, "I want everything to fit together perfectly, with no extra words." He believes that a well-crafted clue can become "like a poem, a beautiful piece of literature."

If he finds he has to clue the word "ATE", he eschews straight synonyms for something shiftier like "downed a sub" or "had wings". He's a big admirer of what he calls a rebus clue, such as "out in spring," which gives both the definition of the answer and the cryptic method of finding it: OUT inside SPRING, meaning SPROUTING.

Mr. Simpson studies language with a connoisseur's eye for misdirection, and notices a suffix such as -sake (keepsake, forsake, etc.) as if it were the Japanese drink of the same name. He keeps a list of words that become new words when a hyphen is added. "The famous example is local and lo-cal," he says. "Then there's a newish one I like, "blister" and "B-lister"."

He also has a complete list of two-letter abbreviations and phrases that might be needed for a segment of a longer answer – "taking a left," in the conventions of crossword phraseology, could be used to clue a word that incorporates ("taking") the common letter combination AL. When reading an article about the film Gone with the Wind, he noticed that the character Suellen consisted of SULLEN wrapped around an E – which, in the crossword's all-embracing world, is bound to come in handy.

A brain that loves puzzles

This dedication to detail pays off in pleasure when solvers manage to unravel the puzzler's tangled clues. And now cognitive scientists have developed a new appreciation for the role of puzzles in our mental development.

Daniel Bor, a neuroscientist at the University of Sussex and the author of The Ravenous Brain, discovered that when the brain is presented with the opportunity to spot patterns, the dorsolateral prefrontal cortex – the part of the brain associated with IQ and consciousness – activates very strongly.

"I argue spotting patterns is the main purpose of consciousness," Dr. Bor says. "When we as an animal are going through our normal habitual lives and everything's okay, we can rely on our instincts and habits. But if we're starving or there's some new predator that's about to eat us, then we have to innovate and have to spot some new pattern that's going to get us out of this rut."

Crossword puzzles in themselves don't help us in daily life. But by their deceptive design, they satisfy a brain that's desperate not to be bored by the same old thing. "The whole point of a challenging crossword is that it can never be automatic," Dr. Bor says. "Searching for novelty is something that's particularly human, and building new patterns is what's really exciting. I can daydream when I drive, even though I have clear memories of a time when I really struggled as a driver. But I'm pretty sure it's impossible to daydream your way to a crossword solution, which is why a puzzle is more fun than driving."

It makes sense that riddles and puzzles have always been with us – Wynne's innovation simply elaborated a constant human preoccupation into a new level of consciousness. The prophesies of ancient oracles dripped with dangerous ambiguity: At Delphi, King Croesus was told that, if he invaded Persia, he would destroy a great empire. He didn't stop to consider that the empire might be his own. At Thebes, the legendary sphinx regularly killed off travellers who couldn't interpret the question, "What creature walks on four legs at dawn, two at noon and three in the evening?"

Words, as employed by the experts, were the stuff of incantations, life-giving remedies, metrical memories that conjured up ancient wars and heroes, dimension-crossing prayers to supernatural beings, and unseen traps for the uninitiated. Over much of verbal history, the playfulness of language served as a modelling of the world's unexpectedness, an ever-present warning against giving in to the habitual and taking things as they seem.

"This kind of activity exists from the beginning of civilization and spans all the various codes that we use to express ourselves," says Marcel Danesi, professor of anthropology at the University of Toronto and author of The Puzzle Instinct. "There's something in the particular way a puzzle expresses a dilemma that intrigues us. The puzzle is the non-obvious: It presents a situation that seems chaotic, and we have an innate instinct to restore order to that situation, to bring the clues together."

It's an instinct of survival, and especially powerful in the very young: How do we make sense of a world that's constantly throwing surprises at us, how do we reorder the cascade of sensory data being hurled at us into an object we can call a chair, or an entity that's recognizable as a friend and ally? Children are especially adept at sorting out visualization puzzles like hidden-word searches and the treasure maps printed on a restaurant's paper placemats – descendants of the mazes and labyrinths that were once the stuff of heroic legends.

Do these lessons of human uncertainty endure in an art-form that relies so much on hidden meanings? Alan Connor thinks so. "With cryptic crosswords particularly, you're always trying to spot ambiguity and realize that what somebody appears to be saying may be the exact opposite of what they mean. It's useful to have that kind of skepticism when you encounter advertising or a politician's speech."

A future without print?

Or maybe skeptics just gravitate to crosswords.

It's a natural tendency to look for the value-added usefulness of a pursuit that takes up so much of our time and penetrates to the best parts of our brain. Alas, there is no research that yet confirms the widespread belief that the mental exercise of the crossword can ward off dementia – doing crosswords simply makes you better at doing crosswords, and whatever joy and self-esteem you get from that should be seen as an end in itself. Certainly there are few mental pleasures that can rival the sensation of walking away from an impossible clue – "Of, of, of, of, of, of, of, of, of, of" – and then suddenly realizing you've found the 10-letter answer, or the answer's found you: OF TEN TIMES, OFTENTIMES.

"All crossword solvers know that experience," Mr. Shortz says. "It could be that the brain is working on this unsolved problem subconsciously. Or it could be like an old-fashioned slide projector: Depending on where the carousel is positioned, a slide may drop down into the slot or it may not."

The mind, concludes the man who should know, is a mysterious thing. Thanks to Arthur Wynne's devious successors, this almost unimaginable euphoria of trickery has been harnessed for human good – assuming, as crossword solvers do, that there is something wonderful about whiling away large parts of life sorting out hidden enigmas.

But what's the future of this difficult and not always welcoming pleasure? The crossword evolved alongside the newspaper, a medium that is questioning its delivery mode.

"Crosswords are ideally suited to the print medium," Mr. Shortz says. "There's something aesthetically pleasing about filling in squares on paper that you don't get online. It's easier and faster to jump around a grid on paper where you can see all the clues at once. But that said, the crossword will survive in a digital world because it's such a good puzzle. And there may be new things that can be done with online clues that can't be done in print, like sounds and pictures."

Mr. Shortz is not shy about saying that the seemingly traditional crossword now makes millions of dollars for The New York Times in online subscriptions, spinoff books and syndication – the brain's high-order addiction to challenging wordplay is that powerful. At The Guardian in England, says crossword editor Hugh Stephenson, the monetizing of the puzzle has been less successful, but the word-game's crafty appeal is just as strong.

Mr. Stephenson, who regularly blogs to his community of readers on such subjects as the Americanization of British crossword language and the legitimacy of new words that haven't found their way into official dictionaries, fields complaints from a global network of Guardian readers who question why they need to know abstruse cricket terms to solve an already daunting puzzle.

"To which my answer," he says, "is that you're going for an English crossword, and I'm afraid cricket is a part of being English."

But why be afraid? It's all a part of the mystery of life at the crossword level of telling detail, where The Simpsons and Modest Mouse and three-letter Australian birds and a cryptic English game can all share a home inside a tiny grid that tantalizes us with its pains and pleasures.

A taxonomy of clues

Getting beyond the definition-driven clues of traditional puzzles expands the pleasures but also the challenges. The learning curve at entry level is steep. But once you've mastered the tricks – and agreed to let your mind wander – the clues don't seem nearly so twisted. Here are some samples:


The magic of rearranged letters is a favourite of crossword maker Fraser Simpson: "Dog in wild" (DINGO) – which shows the PLEASURE we can get from "messing with the tricky ruse and leap of language."


Words that sound alike but are spelled differently can produce a two-part clue where the hint is in the sound cue: WURST is "Said to be inferior sausage." A double-definition clue is used for a single spelling with double meanings: "Small insult" could be a SLIGHT.


A rare bi-directional misdirection: "The wave goes out and back." (RADAR)


Will Shortz, the New York Times puzzle maker, loves a double pun: "It turns into a different story" (SPIRAL STAIRCASE). The Times also goes in for thematic groaners, like the puzzle titled M-M-M, which produced slightly off answers like CRAZY AS A LOOM


Put SH (quiet) within MARY (a lady) and you get MARSHY, and the kind of head-scratching sentence that sounds like a cryptic clue – "Lady keeping quiet describes a wetland." Or how about "Being around Japan's capital, I could be in China." Which is BEING wrapped around J and I.

Hidden word

Staring you right in the eye, and still hard to spot. A neat HIDDEN word from The Daily Telegraph: "How some answers may be found in clues, some of which I'd denoted."

Word chain

The bits-and-pieces approach, often involving abbreviations, many of them British. "It's a team game, therefore cricket club requires one ruling" (6 letters). "Therefore" means SO, "cricket club" is CC and "one ruling" is the ER of our coins, Elizabeth Regina. A deep breath and you get SOCCER, which non-royalists might have guessed anyway from "team game."


"Method to make dirt into dire infusion." (6) The Globe crossword crafter Fraser's Simpson's panoply of torture devices includes this elaborate letter-shift clue. Easiest to start with a six-letter word for herbal infusion, TISANE, and work it out backwards. In what way is "dire" made from "dirt"? Easy: T IS AN E.