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What's the Word?

Crossword-puzzler Al Sanders has had his ups and downs.

This is because the cleverest clues will use mental misdirection in an attempt to throw off pursuers, and solvers must be prepared to follow. "The good ones are where you'll read the clue and you're certain that it's going one way, and then it doesn't," Al says. Whereas an old clue might simply read "mal de mer," the new-style one would hint: "Needing relief from pitching." (The answer to both is "seasick.")

"Who cares about the Babylonian god of dirt?" the notorious "new wave" crossword constructor Merl Reagle once said, explaining his motivation. "Instead of the usual themes, I wanted to do themes like movies that should not be shown together -- like Driving Miss Daisy/Nutz, or Men in Black/Lipstick. Or Three Men and a Baby/Anaconda."

The riddlesome clues have added an addicting element of sweet torment to crosswords. With older puzzles, you either knew the answer or you didn't. Newer puzzles hold out the alluring promise of a sudden solution to every clue if only you think hard enough. They are as much tests of wit as they are of knowledge. Many puzzles now have themes; a few have punchlines. It is hardly surprising that serious solvers have more than a bit of the masochist in them.

Al Sanders works on a puzzle.
Anthony Camera
Al Sanders works on a puzzle.

In fact, the whole dynamic between crossword solvers and constructors is a lot like S&M -- a period of excruciatingly pleasurable anguish at the hands of a master, followed by blissful release. Constructors commonly refer to themselves as torturers; one early British editor was known only by his pen name, Torquemada.

Puzzles that are too easy leave a solver feeling cheap and unsatisfied. On the other hand, "the best puzzles string you along until the end," says Al. Constructors have a name for that balance point between pleasure and pain -- the exquisite area between a patently unsolvable clue and one that makes the solver writhe and then, with a smack of the forehead, break through. They call it the "sweet spot."

The cleverest constructors become celebrities. Especially brilliant puzzles are collected and recalled with awe, like great sports moments or Grateful Dead concerts. One such famous puzzle appeared on election eve in November 1996. A crucial fourteen-letter clue hinted, "Lead story in tomorrow's newspaper." Outraged solvers quickly jammed phone lines, protesting the constructor's chutzpah when they learned the right answer was "Clinton Elected."

Other callers, however, complained that the right answer, "Bob Dole elected," was factually incorrect. What both discovered, of course, was that the constructor had covered his bases -- and earned his place in crossword lore -- by writing the puzzle so that both answers fit perfectly. (The first down clue was "Black Halloween animal"; both "cat" and "bat" worked.)

Crosswords have been called the world's most popular pastime, yet the demographics of competitions are like NCAA women's basketball. While some fifty million people are thought to dabble at wordplay in newspapers, magazines and online, a mere handful of solvers dominate the top ranks, and the gap never seems to close.

The premier tournament in the country is the American Crossword Puzzle Tournament, held annually in Stamford, Connecticut. It is organized and run by Will Shortz, crossword editor for the New York Times(and the only man in the country with a college degree in "enigmatology," a major he designed himself. He also wrote the riddles featured in the 1995 movie Batman Forever).

Although several hundred people enter each year, by the end of the second day of the competition, the field has been narrowed down to just three. Since 1988, four people -- the upstart whiz-kid constructor Trip Payne, Douglas "The Iceman" Hoylman, perennial second-place finisher Ellen Ripstein and cabaret musician Jon Delfin -- have claimed 35 of those 39 spots.

"The chance of someone waltzing into a major crossword tournament and winning the first time out is nil," says Shortz. In fact, the only other player who has cracked the finals more than once besides these four is Al Sanders -- although it always seems to come as something of a surprise when he does. In 1999, Al was in first place going into the finals, a place he'd been before. Still, it drew a big laugh from the audience when the announcer intoned, "And in the center, Al Sanders. Um, I don't know who he is."


Being a crossword genius is not like playing in the NBA, and the stereotype of what big-time gamers might look and behave like is not too far from the truth. Unathletic is a given. Socially peculiar can generally be assumed.

Iceman Hoylman has a mounding belly; his knees brush together as he lumbers along. John Delfin insists on using only No. 1 pencils. Trip Payne is slightly built, weak of chin, and arrogant enough to bring back uncomfortable memories of the straight-A nerd you knew in seventh grade and wanted to punch.

"It's an interesting crowd," Al says. "People are social; they'll stay up all night playing board games. But there are a couple of folks who are tough to strike up a conversation with."

Still, there are similarities. Like Tiger Woods, gifted puzzlers usually demonstrate an early aptitude. Trip Payne recalled that he began figuring out crosswords around the age of three by comparing week-old and current editions of TV Guide. He constructed his first puzzles for the elementary-school newspaper. Will Shortz started writing his own puzzle books when he was ten. In an eighth-grade social studies paper, he confidently announced that he would become a professional puzzlemaker.

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