Quick—what's a nine-letter word for torture? Hint: It's probably the squarest thing you can do in bed, it gets harder as the week goes on, and it draws almost as many Sunday worshipers as church.

If you guessed "crossword," you're right! And you're probably a total geek. But the Daily Show's Jon Stewart, Viagra shill Bob Dole, the Indigo Girls, Ken Burns and our last real president are all right there with you. Each grapples with the New York Times puzzle regularly, and all appear in this entertaining documentary about crossword culture.

Crossword culture? Who knew there was any such thing?

Lots of people, apparently. And they hang out together, once a year, at the American Crossword Puzzle Tournament. From an outsider's perspective, this looks at first glance like a Trekkie convention for smart people. But only at first glance.

The documentary, Wordplay, directed by Patrick Creadon, focuses on the moustachioed enigmatologist Will Shortz, puzzle master of the Times and National Public Radio. Shortz is also the director of the crossword puzzle tournament, held each year since 1978 at the Marriott Hotel in Stamford, Conn.

The buildup to the tournament provides the bulk of the film. Rivalries are set up, dark horses identified. You've got the baton-twirling crossword queen Ellen Ripstein, who won in 2001 and can clearly still taste victory. You've got seven-time winner Jon Delfin and chronic third-placer Al Sanders. You've got flair in the form of Trip Payne, 2004's winner. And you have The Kid, Tyler Hinman, who's lived fewer years than most of these guys have competed.

Then there's everyone else, the 500-odd unfamous competitors, for many of whom this is quite clearly the social event of the year. Portlander Matt Jones, who writes the Jonesin' crossword at the back of WW, has competed in the tournament for eight years and placed in the top 20 seven times.

"I have trouble explaining to my non-puzzle friends what I do and what it's like to be there," Jones says. "Wordplay finally gets it right—it finally shows a human side to the participants and the real camaraderie between people. It's the real reason puzzle fans get together. I mean, get past the few people with the weird puzzle hats and crossword grid pajamas, and you've got an extremely bright group that loves to have fun."

Watching a bunch of charming, intelligent oddballs fill out giant crossword puzzles on stage might not sound like the makings of a wild cinematic joyride, but it's a lot more fun than, say, a doc about people who obsessively read the stockmarket quotes before breakfast. And sure, this isn't the kind of vital documentary that just had to be made. It's frivolous, like the puzzle itself. But, also like the puzzle, Wordplay falls into that particularly nerdy category of leisure-time activity that can almost be disguised as self-improving brainwork. There are victories and disappointments, heartbreak, honor and moustaches. In a film about newspaper readers, you can't ask for much more than that.

Opens Friday, June 23. Fox Tower.