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Wordplay is a 2006 documentary film that follows the world of crossword puzzles and the people who create and solve them. The film features interviews with some of the biggest names in the field, including New York Times crossword puzzle editor and puzzle mastermind Will Shortz, puzzle creators Merl Reagle and Trip Payne, and crossword enthusiasts from all walks of life.

The film opens with a montage of people solving crossword puzzles, both in print and online. These are people who are passionate about puzzles and the challenge of completing them, and Wordplay quickly establishes itself as a film about passion and dedication.

From there, we meet Will Shortz, who has devoted his life to crossword puzzles. Shortz takes us on a tour of his life and career, from his early days as a puzzle creator to his current position as editor of the New York Times crossword puzzle. He talks about his approach to creating puzzles, and his philosophy that a good puzzle should be challenging and entertaining but never frustrating.

The film also explores the world of competitive crossword puzzle solving, which is more intense than one might expect. We meet some of the top competitors in the field, including Tyler Hinman, a seven-time American Crossword Puzzle Tournament champion. The competition is fierce, but the atmosphere is surprisingly friendly and supportive. For these competitors, the thrill of the puzzle is in the solving, not the winning.

Along the way, the film introduces us to some of the more eccentric characters in the world of crosswords. There's Ellen Ripstein, a legendary crossword puzzle creator known for her cryptic and clever clues, and Jon Delfin, a former National Scrabble Champion who approaches crossword puzzles with the same intensity as competitive Scrabble.

The film also delves into the history of crossword puzzles, tracing their origins back to the early 20th century. We learn that crosswords were initially dismissed as a fad, but they quickly became a nationwide obsession. There are some fascinating tidbits of trivia here, such as the fact that during World War II, the Allies used crossword puzzle clues to encode secret messages.

One of the most entertaining parts of Wordplay is watching celebrities solve crossword puzzles. We get to see Jon Stewart, Ken Burns, and Mike Mussina take on the New York Times puzzle with varying levels of success. It's fun to see these famous faces grapple with the same challenges that millions of people around the world face every day.

The film also highlights the role that crossword puzzles play in our culture. Crosswords have been featured in countless movies, TV shows, and novels, and they have become a staple of modern life. From the infamous 'Dewey defeats Truman' headline to the modern-day obsession with puzzles like Sudoku, Wordplay demonstrates just how deeply rooted crosswords are in our collective consciousness.

As the film nears its conclusion, it focuses on the 2005 American Crossword Puzzle Tournament, the biggest and most prestigious event in the world of competitive crossword puzzle solving. We see the top competitors battling it out in a series of grueling rounds, all leading up to the championship finals. The tension is palpable, and the excitement is contagious.

In the end, Wordplay is an engaging and entertaining documentary that celebrates the joy of puzzles, the thrill of competition, and the power of passion. It's a film that will appeal to anyone who has ever been stumped by a crossword clue or who has felt the satisfaction of finally completing a puzzle. Whether you're a hardcore puzzle enthusiast or just a casual solver, Wordplay is a must-see movie.

Wordplay is a 2005 documentary with a runtime of 1 hour and 34 minutes. It has received mostly positive reviews from critics and viewers, who have given it an IMDb score of 7.4 and a MetaScore of 73.