If you don't already enjoy crossword puzzles, then Wordplay is a documentary you can probably skip because it doesn't offer much in terms of film-making to rope in casual viewers; Wordplay is no Spellbound (which I haven't seen yet -- it's in the queue).
In my case, I do enjoy crossword puzzles, but having no experience of them beyond the narrow role of amateur solver, the movie is enormously informative. For starters, it shows how a crossword puzzle is constructed: we see one constructor, Merl Reagle, create a puzzle from scratch by first coming up with a theme, then positioning the theme words in a blank grid, and lastly filling out words and black squares around those theme words. For something so rigorously structured -- not just the grid, but the rules and conventions passed down from the NY Times' first crossword editor Margaret Farrar forbidding the use of words like "urine" and the orthographically seductive "enema" -- a crossword puzzle is borne out of a tremendous act of intuition that requires a Nabokovian facility and playfulness with words.
(A personal note: the puzzle that Reagle composes virtually on camera is one that I vaguely remember doing, based mostly on my fuzzy recollection that one of the answers was "CROSSSWORDS" -- you don't forget a thing like that triple-S -- even though the centerpiece of the puzzle was "WORD*PLAY.")
The other draw that Wordplay offers is its focus on four or five champion-level solvers, and once again, seeing these people perform smacks my gob. Because of constraints on my time, I don't do Monday through Saturday puzzles anymore (the Sunday Times puzzle is my weekly indulgence), but back when I did, I solved them at an exceptionally leisurely pace. Then, I watch this film and some of the tournament people, as warm up, solve a random puzzle in under in less than 3 minutes. AND THEN, at the final championship round of the 2005 American Crossword Puzzle Tournament (apologies for linking to such an unattractive site), watching the top three tournament contestants blaze through a puzzle whose first word is "ZOLAESQUE" in under 15 minutes (I take the whole week to do a Sunday puzzle) staggers my mind.
As cause for self-reflection, I've realized that I'm overly cautious when I do my puzzles -- my gridless marginalia can get pretty extensive -- and most of the time plunging ahead with an educated guess works out for not just the tournament-level solvers, but amateur (if celebrity) fans featured in the film like Jon Stewart, Bill Clinton (!), and Stanford/Yankee scumbag Mike Mussina (I kid, he's probably a surprisingly tolerable douchebag) (aside from Clinton, though, the celebrity factor isn't that interesting). Really, the boldest thing about my crossword game is that I do puzzles in ink, but that's only because pencil and newsprint aren't a good combination, but after watching the film, I've resolved to be a little more aggressive, starting with the current Sunday puzzle called "Ahead of the Curve," googling which has led me to the Wordplay blog of the Times.
Indie rating: Julien Neto - "I (One)"