Wordplay is mostly exactly what you would expect from a documentary about crossword puzzles and the people who love them. The film begins by introducing us to a number of solvers, including Will Shortz, the editor of the New York Times crossword (and the film's main character, as much as it can be said to have one), the highest ranked amateur crossword puzzle solvers (based on their history at the Annual Crossword Puzzle Tournament in Stamford, Connecticut), and a number of celebrity solvers, like Jon Stewart, Bill Clinton and the Indigo Girls. As we get to know these solvers, the film moves toward its climax, the final round (a three-man showdown) of the 28th crossword tournament.
The film mostly works; the tournament is exciting. Even as all the solvers continue to insist that the tournament is just for fun, it's clear that there's something bigger at stake for all of them. However, this is where the film falls short. As we're introduced to each of the tournament solvers, the film obviously regards their earnestness with the slightest level of contempt. Rather than examine why these solvers are so rabid and what it is that drives them to compete at these levels, we're treated to their most awkward moments; it's funny and mostly good-natured, but not without derision.
A documentary about crossword puzzle solvers is probably going to draw an audience of crossword puzzle solvers and had Patrick Creadon, the filmmaker, shown a little more respect to both of those groups of people, the film may have been able to transcend from a cutesy niche documentary to something bigger than the subject matter.