Wordplay is a 2006 documentary film directed by Patrick Creadon. It features Will Shortz, the editor of the New York Times crossword puzzle, crossword constructor Merl Reagle, and many other noted crossword solvers and constructors. The second half of the movie is set at the 2005 American Crossword Puzzle Tournament (ACPT), where the top solvers compete for a prize of $4000. Wordplay was the best reviewed documentary film of 2006, according to Rotten Tomatoes.Wordplay was acquired for distribution for $1,000,000 by IFC Films and The Weinstein Company after being nominated for the Grand Jury Prize at Sundance 2006. It was released theatrically on June 16, 2006. The film ran in over 500 theaters across the United States, including at least one theater in all fifty states. Wordplay went on to gross $3,100,000 in domestic box-office, then ranking it among the Top 25 highest grossing documentaries of all time.A 2008 episode of The Simpsons, "Homer and Lisa Exchange Cross Words", is based on the film. James L. Brooks got the inspiration for the episode after watching Wordplay. "We felt both Will and Merl were very compelling, off-the-beaten-track personalities [in Wordplay], who would fit into our universe very well," Brooks said. The episode was written by Tim Long, and directed by Nancy Kruse, and guest starred crossword puzzle creators Merl Reagle and Will Shortz as themselves.

Creadon and his wife, producer Christine O'Malley, borrowed $100,000 from family and friends to make Wordplay over the course of 2005–06.