Back in May 2009, I directed readers to the "chess rhapsodies" of Lucio Etruscus, which set clips of cinematic chessplaying to music. Today ChessVibes offers up a complete rhapsody filmography in "Chess in cinema -- the ultimate collection" for anyone who wants to track down the films referenced in these videos.
Chess appears with incredible frequency on film because it provides an instant and visually attractive marker of distinction, intelligence, or cunning in the characters with which it is associated. To get a good sense of the sheer number of films in which chess appears, check out the website Citazioni scacchistiche nei media; the blog Echecs, cinéma, TV...léger; Bill Wall's list of Movies with Chess Scenes; and the website Chess in Cinema. For the truly obsessed, I recommend Bob Basalla's excellent Chess in the Movies.