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The man most associated with crossword puzzles is New York Times puzzle editor and NPR puzzle-master Will Shortz. Director/co-writer Patrick Creadon introduces us to this passionate hero, and to the inner workings of his brilliant and often hilarious contributors, revealing the process and allure of this uniquely American pastime. The odyssey leads to the American Crossword Puzzle Tournament, an annual challenge founded by Shortz which is as much about community and camaraderie as it is about competition. Featuring interviews with celebrity crossword puzzlers such as Bill Clinton, Bob Dole, Jon Stewart, Ken Burns and Mike Mussina.

 Thinking Inside the Box

Inspiration comes in all shapes and sizes. In our case, inspiration came in the form of three crossword puzzle books we received on Christmas morning in 2004.

My wife Christine O’Malley and I had been looking for a great topic for our first feature-length documentary. I’d been working as a cameraman since 1989, and she’d been producing documentaries for years, but we’d never done a project that was truly our own. We’d also been New York Times crossword fans for years, and always wondered what Will Shortz—the editor of the puzzle—was like. After receiving those three crossword books as gifts, I went online to see if I could find the definitive Will Shortz documentary. I figured that by now someone had made a film about this fascinating, somewhat mysterious man. The moment I realized this film had yet to be made was really the first day of production for what would become Wordplay.

“You’re making a film about crossword puzzles? That’s a terrible idea!” This was the input we received from one of our colleagues and close friends, and several other friends of ours shared his feelings. “It’s not that the topic isn’t interesting,” he added, “but you’ll never be able to make it exciting.” Christine and I took this as a challenge, and forged ahead. We’ve always believed that any topic can be interesting—even exciting—so long as the story is told well.

With Will Shortz as our anchor, we decided to fill out the film with a handful of people who compete annually in the American Crossword Puzzle Tournament (which Will has directed since 1978), crossword constructor extraordinaire Merl Reagle (who takes us through the process of actually constructing a crossword), and some famous fans of the puzzle. First on this list was President Bill Clinton, who has been a fan of the New York Times crossword for years and had written to Will on several occasions.

Not only is President Clinton a fan, but he was also included in one of the most famous crosswords ever constructed, which ran on Election Day 1996. A puzzle constructor named Jeremiah Farrell had figured out that the names CLINTON and BOB DOLE—each with seven letters—could be arranged in a puzzle in such a way that both answers could fit. The clue was “Lead story in tomorrow’s newspaper(!),” and the answer was CLINTON ELECTED or BOB DOLE ELECTED. What made the puzzle so astounding was that Dr. Farrell had figured out seven downward clues that could have two different answers (“Black Halloween animal” could be either CAT or BAT; “French 101 word” could be LUI or OUI; “Trumpet” could be BLAST or BOAST, etc…). “It’s just amazing that someone could think of that,” said the President. “Half the time I do these things just to see what people are thinking about.”

We figured getting an interview with President Clinton would be extremely difficult, but we submitted a request anyway. To our complete shock the person we contacted said that the President was aware of our film and that they would try to schedule us an interview. Several months later we did in fact get the interview.

Months after that, we were also fortunate enough to get an interview with Senator Bob Dole. His staff originally turned down our interview request, citing the fact that he was not a huge crossword fan, only to call back later to say that he’d changed his mind and would be happy to meet with us. As he walked into the door at the hotel room where we did the interview, he looked me in the eye and said, “You have quite an advance man working for you.” I did a quick double take, not knowing exactly what he was referring to, when he added, “Two weeks ago I got a call from Bill Clinton saying I really should take part in this crossword puzzle movie…It’s terrific.”

Other interviews included the singing-songwriting team Indigo Girls, Yankees starting pitcher Mike Mussina, documentary filmmaker Ken Burns, former New York Times public editor and author Daniel Okrent, and comedian and The Daily Show host Jon Stewart. Not only are all of these people exceptionally talented and at the top of their respective careers, they are all die-hard New York Times crossword fans. We tried to determine what it was about the puzzle that drew them in every day and how the puzzle helped them in their various fields of expertise.

Though the film is filled with famous crossword puzzle solvers, the real stars of the film are the people who train every year to compete in the annual American Crossword Puzzle Tournament in Stamford, CT. Their drive to be the best, coupled with their decency and camaraderie, is the real heart of our film. After screenings at Sundance last January, dozens of audience members approached Christine and I and commented on how incredibly exciting the film is.

Exciting. Who would have thought crossword puzzles—and the people who solve them—could be exciting? Even we weren’t sure what impact Wordplay would have on an audience as we started working on it after Christmas of 2004, but we knew the topic was important to us and that ultimately that was all that mattered. The process of heading to theatres is an extremely gratifying one for any filmmaker, but for first-time independents like Christine and me, it’s almost too hard to believe. Sometimes you just have to ignore other people’s advice, even when it comes from a good friend.