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Tales From the Cryptic

Patrick Creadon’s Wordplay Gamely Explores Crossword Puzzles, Their Makers, And Fans

PUNNYMAN: Director Patrick Creadon follows puzzle maker Will Shortz (top).

By Violet LeVoit | Posted 6/28/2006

Documentarian Patrick Creadon remembers a particularly vexing struggle with a crossword puzzle. And he wasn’t even the guy doing the solving. His brother-in-law had finally untangled a fiendishly twisted set of clues while on the train ride home and reported to Creadon, I was so excited I almost hugged the guy sitting next to me. “With crossword puzzles, there’s such a great feeling when you finish it, when you’re done and you got it right,” Creadon says. “There aren’t that many things in life that have a perfect solution.”

Creadon, sitting in the lobby of the Washington Madison Hotel with his gee-whiz smile and teddy-bear beard, looks like the grown-up version of the happy kid on a cereal box. It’s not startling to learn his first movie gigs were as a child actor—the Internet Movie Database lists his earliest credit as playing “Tom Sawyer” in a 1982 TV movie, a casting choice that still seems plausible. He’s guileless and generous in person. When he asks, “Have you met Bill Clinton?” or “Have you been to Sundance?” there’s no one-upmanship, just curiosity if you’ve also shared some of the totally rad experiences gifted to him during the completion of his feature documentary Wordplay.

Imagine a typical crossword puzzle, with its four row-spanning phrases that link thematically and give the puzzle a unifying structure. The obliquely constructed Wordplay is no different. Here, the big four are Will Shortz (the only man with a college degree in “enigmatology,” the study of puzzles); the New York Times crossword puzzle, of which Shortz has been editor since 1993; those who love crosswords (famous—the Indigo Girls, Mike Mussina, Bill Clinton, Jon Stewart—and not); and the Annual Crossword Puzzle Tournament, a brainchild of Shortz’s held every spring in Stamford, Conn. Interlaced through those big four are the history of crosswords in America, how to construct a puzzle, profiles of top contestants such as Ellen Ripstein and Trip Payne, and illustrative play-along graphics that let the audience solve the puzzles. By the time the movie gets to the tightly interwoven resolution, you’re satisfied that crossword puzzles are America’s greatest unacknowledged indigenous invention.

True to Creadon’s untortured persona, there’s no profound reason why he and wife Christine O’Malley (the doc’s producer) decided to make a movie about crosswords. Both longtime fans of the New York Times puzzle—Creadon describes their facility, on a scale ranging from Monday’s piece-o’-cake to Saturday’s brain-scorcher, as “somewhere between Wednesday and Thursday”—a Christmas gift of three different Will Shortz puzzle books got them thinking they’d like to watch a Shortz documentary. After finding out that no such program existed, Creadon, who had long ago left acting for a career as a cinematographer, decided this was the feature project he’d been looking for. A phone call to Shortz quickly got the ball rolling—and then Shortz told them about the tournament.

“We weren’t going to do the tournament because we didn’t even actually know there was a tournament when we started,” Creadon says. “And then he’s like, ‘You gotta come to my tournament. If you’re going to do a story about me, the tournament is a big part of my life.’ I remember thinking, Crossword tournament? I don’t think so. That’s going to be kinda boring.

But Creadon reconsidered, and in doing so gave Wordplay its backbone. Like other recent competition-centric documentaries like Spellbound and Mad Hot Ballroom, the audience investment in the final showdown elevates the proceedings from a Discovery Channel curiosity to a movie with a real dramatic arc, complete with heartbreak and glory. “People who like crossword puzzles are almost always very intelligent, have good sense of humor, they like a challenge,” Creadon says. “So, right off the bat, that’s a really interesting cast of characters to fill your movie out with.”

Those characters, from shaggy crossword constructor Merl Reagle (who observes reflexively upon seeing a Dunkin’ Donuts sign that it can be anagrammed to “Unkind Donuts”) to pastel-clad doyen Trip Payne (who observes in an inimitable deadpan, “I’ve always been fascinated by the letter ‘Q’”), share not only cleverness but an unvarnished niceness, making spending 94 minutes in their quick-witted company a pleasure. And no matter their eccentricities, Creadon is kind to his subjects. In less gentle hands, someone like the endearingly awkward Ellen Ripstein—one of the top-ranked woman in the competitive puzzle circuit, she earned the 2001 championship after a 19-year close-but-no-cigar streak that earned her the sobriquet “the Susan Lucci of crosswords”—could have been ripped to pieces, but when Creadon shoots her practicing her baton twirling in Central Park amid Christo’s Gates, there’s no malice in his gaze.

To enhance a competition Creadon describes as “unfilmable”—people quietly filling in little boxes does not make for great cinema—he made the decision to supplement his footage with split-screen graphics of blank grids completing themselves as the solvers decipher increasingly opaque clues. “They’re incredible,” Creadon gushes about the graphics. Visual effects artist Brian Oakes “is a good friend of mine, and we’ve worked together for a long time. Brian basically used the newspaper as the jumping-off point and stepped it up a little bit and made a visually arresting presentation.” Sure enough, playing along with the contestants gives the audience a greater appreciation for the brainpower necessary to turn a jumble of cryptic clues into an orderly matrix of letters.

Much to his surprise, Creadon’s pet curiosity project made the cut at this year’s Sundance Film Festival and sold to a distributor at the festival. “There are people who will try to convince you that Sundance is overly commercial, or there’s too many parties with too many big sponsors, blah blah blah, whatever,” he says. “First of all, if it wasn’t for Sundance, our film and a lot of films like ours would never get out there. But the other thing is, our funding for arts is pretty dismal by comparison to other countries. And I certainly don’t want to get on a soapbox for that, but I’m glad that companies come out and try to support young independent filmmakers. We owe everything to Sundance and Silver Docs and Tribeca Film Festival and a few other festivals we went to. Without them, you can’t get discovered.”

And so, just a few days from the Fourth of July, Creadon’s doc enters theaters nationwide. Maybe it’s not some hardened producer’s idea of a patriotic movie, but Wordplay makes the case that a crossword puzzle tournament is as American as a pie-eating contest—just as fun, a little silly, but much, much more cerebral. And who says Americans can’t be cerebral while they’re having fun? “I’ll be the first to admit there’s not a lot of gravitas to our film,” Creadon says. “But we’re completely unapologetic about that. It’s a really funny film that makes people feel good.”

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