An in-depth look at The New York Times' long-time crossword puzzle editor Will Shortz and his loyal fan base.


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Cast overview, first billed only:
Merl Reagle ...
Tyler Hinman ...
Al Sanders ...
Ellen Ripstein ...
Jon Delfin ...
Emily Saliers ...
Mike Mussina ...
Himself (as William Jefferson Clinton)


A documentary that focuses on the world of crossword puzzles: those that construct them, those that love to solve them, those that compete in the annual Crossword competition in Stamford and also on Will Shortz, the editor of the New York Times crossword since the early 1990s. Shortz actually has a university degree in games and organized the first crossword championship in 1978. Some of the contributors to the Times puzzle explain how they go about building them while some aficionados, including former President Bill Clinton and comedian Jon Stewart talk about their love of solving them. The film also introduces several past champions and near champions competing in the 2006 tournament and it takes you from the preliminary rounds to the final where the top three contestants compete in front of a room full of admiring contestants. Written by garykmcd

Plot Summary | Plot Synopsis


A wildly entertaining documentary about crossword puzzles, the people who make them and the people who love them See more »



Motion Picture Rating (MPAA)

Rated PG for some language and mild thematic elements | See all certifications »


Official Sites:




Release Date:

21 July 2006 (USA)  »

Also Known As:

Word Play  »

Box Office

Opening Weekend:

$32,847 (USA) (16 June 2006)


$3,117,666 (USA) (20 October 2006)

Company Credits

Show detailed on  »

Technical Specs

Sound Mix:


Aspect Ratio:

1.66 : 1
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Did You Know?


Tyler Hinman would eventually work for Google for a few years. See more »


Tyler Hinman: [Asked how he feels after winning the crossword puzzle tournament] Words are failing me. I'm glad they waited until now to do so.
See more »


References Kate & Allie (1984) See more »


This Must Be the Place (Niave Melody)
written by David Byrne, Chris Frantz, Jerry Harrison, and Tina Weymouth (as Martina Weymouth)
performed by Shawn Colvin
See more »

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User Reviews

Low-Key But Surprisingly Enthralling Look at a Most Unlikely Subject
24 January 2007 | by (San Francisco, CA, USA) – See all my reviews

I have half-heartedly tried the New York crossword puzzles on occasion but had no idea what a devout following they had until I watched this refreshing 2006 documentary. Structured a bit like 2002's "Spellbound", the entertaining film that builds toward the 1999 Scripps National Spelling Bee, first-time director Patrick Creadon uses the 2005 American Crossword Puzzle Tournament as his climactic event where a group of nimble-minded crossword solvers vie for the championship. However, Creadon wisely focuses much of the film's initial attention on Will Shortz, the crossword puzzle editor for The New York Times who has gained renown as NPR's Puzzle Master. At his post since 1993, he has dramatically transformed the puzzle from an often frustrating, intellectualized exercise full of obscure clues to a more broad-based challenge that embraced popular culture and word games.

The change has engendered a diverse number of celebrity fans, several interviewed here in entertaining snippets - a particularly caustic Jon Stewart, Yankees pitcher Mike Mussina, the Indigo Girls, filmmaker Ken Burns in a somewhat zen-like state, a wry Bob Dole, and Creadon's biggest get, an ingratiating Bill Clinton who conquers his puzzle with surprising zeal. Once the film turns its attention toward the tournament, the personalities of the top contenders are highlighted with the makings of a classic showdown among three-time champion and professional puzzle-maker Trip Payne; Al Sanders, the middle-aged perennial also-ran who can never seem to rank above third; and prodigious twenty-year old Tyler Hinman, the potential usurper who could become the youngest champion ever. One of my favorites is Ellen Ripstein, an unassuming statistician who twirls a baton, but the true unsung hero of the piece has to be frequent Times puzzle creator Merl Reagle.

Delving into the crossword puzzles themselves, the most interesting extra with the 2006 DVD is a featurette called "Five Unforgettable Puzzles" about how the five of the most challenging Times puzzles were constructed as recounted by the creators themselves. Naturally, the puzzles are included in the accompanying booklet as well as the DVD-ROM for printing. The DVD also includes an amiable and insightful commentary track by Creadon, Shortz and Reagle, as well as a bevy of deleted scenes, including extended versions of the celebrity interviews. There is a twenty-minute short about the film's reception at the 2006 Sundance Festival, including a Q&A with the top contenders, as well as a music video. It's a robust package for a niche-oriented film but one that is more entertaining than it has any right to be.

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