For people drawn to such a solitary pursuit, crossword puzzlers are revealed to be a wonderfully warm, geeky, and surprisingly funny crowd in this documentary profile about Will Shortz—puzzle editor for The New York Times since 1993—and his acolytes, who, truth be told, spend no small amount of time cursing their hero. In a quick montage of good-natured complaint letters, we hear, "It's Monday, Mr. Shortz! Not Friday!" Such is Wordplay's affectionately inside tone that nowhere is it explained that the Times puzzles get harder through the week. If you don't already know that kind of stuff, you're probably happy with stale bagels and stand still on escalators, too.
Director Patrick Creadon follows contestants to the 28th American Crossword Puzzle Tournament (established, naturally, by Shortz, who also self-designed his own '70s undergraduate degree in "enigmatology"). One's a college kid, one's a baton twirler, one's a software engineer, one's a professional rehearsal pianist on Broadway, and all of them in under 15 minutes can solve a puzzle that might take you or me a couple of hours. They're all so damn likable, and yet you kind of hate them for their awesome wordsmithery. As the film notes, none is a professional writer or editor; instead, each has a kind of speedy pattern- recognition intelligence and a cunning with clues and reverse-engineering answers. We also meet brainy professional puzzle designers who submit their work to Shortz each week; one speaks of placing his clues and squares "so the diagram breathes a little." I'm guessing that one ended up on a Wednesday.
And there are celebrity puzzlers: Bill Clinton, Bob Dole, the Indigo Girls, Yankees pitcher Mike Mussina, Ken Burns (who compares puzzles to "a city of grids"), and The Daily Show's Jon Stewart, who lauds Shortz as "the Errol Flynn of crossword puzzles." Maybe so, and certainly he's the leader of what the pianist calls "a lost tribe" that loyally gathers in Stamford, Conn., each year to match wits. I'd love to see you there sometime, but I'm still working on Thursday from two weeks ago.