An in-depth look at The New York Times' long-time crossword puzzle editor Will Shortz and his loyal fan base. "Wordplay" starts the story of the New York Times crossword puzzle, and the current and historical creative forces behind it. But as it dances across the story, filling it in as one of its devotees might across the puzzles, it reveals an entire amazing world behind its practice, creation, and history, from the annual crossword convention in Stamford to the breadth of individuals who enjoy it daily.