Will Shortz has edited the New York Times crossword for over twenty-five years and hosts a weekly puzzle segment on NPR, and director Patrick Creadon follows him from a puzzle-obsessed childhood to that job while building the film around the American Crossword Puzzle Tournament. Constructors Merl Reagle, Ellen Ripstein, and eventual champion Tyler Hinman explain how a themed grid actually gets built, symmetry, wordplay, and all, while a cluster of devoted regulars who call themselves "the Crazies" show up year after year to compete against each other and against the clock. The film also digs into the puzzle's own history, including a scandal in the paper's early crossword days that nearly killed the feature before it became a daily institution. Fans interviewed on camera range from ordinary solvers to Bill Clinton and Jon Stewart, all describing the same pull toward a small grid of black and white squares. The tournament footage carries the film's tension: solvers racing pen against paper, seconds counting, one puzzle deciding who gets to be champion that year.