Are you looking for entertainment or instruction?
For entertainment:
I liked the movie "Searching for Bobby Fischer". I don't think it's been made into a movie, but the musical "Chess" is worth watching IMHO. "Geri's Game" the animation short from pixar was entertaining too. Ther is also a YouTube-ish site devoted to chess at http://www.chessmovies.com/ Maybe all that is no-brainers, but its a start.
For instuction I usually pick up a book. :( I'm no help there.
What a good chess movie that you've watched and you would reccomend it.Please comment good chess movies.