"Wordplay" is a documentary looking at Will Shortz, the famous crossword editor ot the New York Times, and his work with the American Crossword Championships. We meet several celebrities who have a passion for the Times crossword puzzle, including Jon Stewart, Mike Mussina and the Indigo Girls. We also watch as puzzle writers and enthusiasts from across the country gather in a nondescript hotel in Stamford, Connecticut, for a weekend that's part championship competition and part family reunion. There are discussions about how crossword puzzles came to be, what it takes a create a good puzzle, and what it takes to become a world-class solver.