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

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“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.

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