Wordplay is a delightful documentary from 2006, featuring Will Shortz, editor of the New York Times crossword puzzle, and his band of merry crossword enthusiasts.
From the IMBD description:
A documentary that focuses on the world of crossword puzzles: those that construct them, those that love to solve them, those that compete in the annual Crossword competition in Stamford and also on Will Shortz, the editor of the New York Times crossword since the early 1990s. Shortz actually has a university degree in games and organized the first crossword championship in 1978. Some of the contributors to the Times puzzle explain how they go about building them while some aficionados, including former President Bill Clinton and comedian Jon Stewart talk about their love of solving them. The film also introduces several past champions and near champions competing in the 2006 tournament and it takes you from the preliminary rounds to the final where the top three contestants compete in front of a room full of admiring contestants.I spent a thoroughly enjoyable hour and a half visiting the world of crossword puzzlers via this film, and it's a world in which winning the competiton is important, but connecting with others who share your passion for an activity is more important. The intensity, the cameraderie, and the sheer word-power of everyone featured in the film made it a joy to watch.
I became a Will Shortz fan from listening to him on NPR's Weekend Edition--the puzzle section is my favorite section by far--and this documentary makes me think he's got to be one of the nicest people on the planet. Creating an annual event so that all his puzzle-heads can get together regularly for a puzzle-fest is more than kind.
Looking for a feel-good movie? This is it!