Will Shortz | Playing With Words

Listen, why can’t Dr. Dre be in the puzzle? Or why can’t the Indigo Girls be in the puzzle? Why does it have to be obscure language that no one’s ever heard?



This is a man who is very, very famous, but no one knows anything about him,” says Patrick Creadon, the director of the new documentary Wordplay, about his subject, New York Times’ crossword puzzle editor Will Shortz. Jon Stewart, one of the interviewees in the film, asserts, “When you imagine ‘crossword guy,’ you imagine he’s 13 or 14 inches tall… [and that he’s] someone who doesn’t care to go more than five feet without his inhaler.” If you were to wander into a bookstore (especially an airport bookstore), you would be inundated with books Shortz edited, featuring puzzles he edited, but these days, the omnipresent books are sudoku, instead of the puzzles on which Shortz made his name: the crossword puzzle. Anyone who has done even a single crossword puzzle in the past decade or so has more than likely born witness to Shortz’ work, even if it wasn’t a Shortz-edited puzzle.

Shortz is credited with revolutionizing the crossword puzzle, making it palatable to a mass audience, instead of the team of geriatrics such puzzles once targeted. Tongue-in-cheek clues, pop culture references, theme puzzles—all are techniques invented and/or perfected by Shortz. According to Creadon, “When Will took over the puzzle, he came in and said, ‘Listen, why can’t Dr. Dre be in the puzzle? Or why can’t the Indigo Girls be in the puzzle? Why does it have to be obscure language that no one’s ever heard?’ And by doing that, he brought in a young, fresh audience.” A good example of the type of tomfoolery that brought recognition to both Shortz and his crosswords can be found in the puzzle on the eve of the 1996 presidential election. An across clue for a seven-letter word read, “Tomorrow’s headline: ______ wins election.” As it turned out, either “Clinton” or “Bob Dole” would fit in the space; all of the perpendicular down clues were worded as such so that they would fit with either letter associated with either answer (such as for the first letter, a three-letter word where the second and third letters were “at,” had the clue “Black Halloween animal,” so that the answer could logically be either “bat” or “cat”).

Aside from having his name at the top of the best crossword puzzles in the country (if not the world), you might recognize Shortz’ name from hearing him on NPR, or from the aforementioned sudoku or numerous other puzzles and puzzle books he edits (his degree is in enigmatology, the study of puzzles). “I didn’t even realize that the film was about me until it was done. I thought it was about the American Crossword Puzzle Tournament,” says Shortz when I ask him how he felt when he learned of the documentary. The American Crossword Puzzle Tournament is a competition that Shortz founded and directs every year for crossword puzzle aficionados to compete in speed runs across the nation’s best, and this tournament is where Wordplay concludes, so Shortz’ erroneous assumption isn’t improbable.

Before I headed to Sundance this past January (which is where Wordplay had its world premiere, and became the one true out-of-nowhere hit of the festival), I had been telling friends and family about the films I was looking forward to seeing. I mentioned that a film about Will Shortz looked like it could be good. Much to my surprise, people I had known all my life—people who had never let on that they enjoyed crossword puzzles—were emphatic about how much they loved Shortz. I quickly learned of his absolutely fanatical following (you should have seen the wait list line at all of Wordplay’s Sundance screenings). “Surveys show that more than 50 million Americans solve crosswords at least occasionally, but usually we don’t know who they are because we don’t do crosswords together,” explains Shortz about the phenomenon.

Shortz doesn’t write the crossword puzzles himself, but since he handpicks the ones that wind up in the paper and fine-tunes the answers and clues, all of the ones that he works on bear his unmistakable mark. (Wordplay profiles some of the more proficient and well-known actual crossword puzzle writers, as well.) If you’re interested in making a crossword puzzle for yourself, Shortz explains, “There’s a great Web site called cruciverb.com. It’s the Web site and forum for crossword constructors; they give you all of the rules and specifications for submitting a crossword.” One might worry that if Wordplay catches on, Shortz will soon be inundated with unsolicited, crappy crossword puzzles, but he seems unfazed by the prospect. “I can handle anything. I do wonder—the capacity at the hotel where we have the crossword championship—we’ve reached our limit. I don’t know what we’re going to do. It would be a wonderful problem to have, too many people.”

Creadon is matter-of-fact when asked if his film will appeal to mass audiences, not just crossword puzzle aficionados. “Our number one goal is to make a movie for non-crossword puzzle fans,” he says. “You don’t have to be a basketball fan to really love Hoop Dreams.” Granted, it might be true that you don’t have to love crossword puzzles to enjoy Wordplay. But I would venture to guess that you’ll be won over to the world of crosswords after seeing this film.

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