To me, a successful documentary teaches me about someone or something I didn't know. I am not a crossword enthusiast, but I thought I knew about crossword puzzles. It turns out there is a lot I didn't know, and what I learned in "Wordplay" was conveyed in an entertaining manner.
The film is rated PG, and the only mildly "offensive" language occurs when one of the puzzle constructors lists several clinical terms that he is not allowed to use in the puzzles. It's nothing you wouldn't hear at your annual physical.
Wordplay is one documentary with three interwoven parts. The first part introduces us to New York Times crossword puzzle editor Will Shortz and a number of puzzle constructors, primarily Merl Reagle. It shows how crossword puzzles are created and edited. It explains the "rules" of puzzle-making, how the degree of a puzzle's difficulty is changed by altering the clues, and how creators use themes throughout the puzzle. It also shows how there are often puzzles within the puzzle.
The second part is a series of interviews with six or seven celebrity crossword enthusiasts, and with a number of competitors in the annual tournament. One of the most interesting parts of the film is watching each of the celebrities work on the same puzzle at the same time. The filmmakers use split screens and animation to show the answers being filled in.
The third part (and the bulk of the film) covers the 28th American Crossword Puzzle Tournament held in March, 2005 in Stamford, CT. It features more cool puzzle-filling animation, and it includes a blunder of Bill Buckneresque proportions. The tournament is a nerd-fest of the highest order (not that there's anything wrong with that). It's a combination competition, convention, and family reunion. The participants seem like nice people who genuinely enjoy each others' company. There is one scene with an element of sportsmanship that is rarely displayed in competition on any level.
You MUST watch ALL of the bonus scenes on the DVD. OK, you can skip the music video, but watch the rest of them. In their entirety they are about as long as the movie itself (94 minutes). They include deleted scenes, extended cuts from the celebrity interviews, additional insight into the puzzle creation process, and more clips from the tournament.
There is also a short film about a group of people in a small Wisconsin town who read The New York Times every Sunday. This segment is a little out-of-place if not off-putting. It is not about the puzzle at all, it's just about people who read The Times. I found these people to be elitist and condescending -- not at all what I expected from a rural town in Wisconsin. One of them even admits to "playing at" being a farmer while not at his "home" in Chicago. The point of the film seemed to be that erudite urbanites love spending time in the country as long as they can get a decent cup of coffee and the Sunday New York Times. If I lived in that town I would buy up all of the papers every Sunday so these people would go back from whence they came.