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No Direction Home: Bob Dylan (2005; dir. Martin Scorsese) Even at three hours, this documentary only scratches the surface of one of music's most fascinating artists. The film covers the songwriter's early years in Minnesota, as part of the New York folk scene, up through the controversial decision to "go electric." Scorcese treats the chorus of boos that followed Dylan on his '65 tour as a backing track for the film—a constant reminder of his outsider status. It's hard being the voice of a generation when no one cares what you have to say.
Office Space (1999; dir. Mike Judge) Now you no longer have to wait for Comedy Central to show this every three days; you can watch it anytime you want. Office Space is one of many comedies that wasn't (believe it or not) a hit in its original theatrical release but only gradually gained cult status through home video and endless cable showings. Infinitely "rewatchable," the scene where the three office mates beat the crap out of a malfunctioning computer printer is alone worth the price of your monthly Netflix subscription. Just don't touch my stapler...
The Twilight Samurai (2002; dir. Yoji Yamada, Japanese language) A poor samurai, resigned to living the rest of his life in anonymity, gets the call from his clan superiors to do a job that nobody else wants. Very deliberate in the unravelling of plot and its navel gazing, but filled with some quietly beautiful moments.
The Thin Blue Line (1988; dir. Errol Morris) As suspenseful as any narrative film you'll see, The Thin Blue Line is Errol Morris' masterpiece about a mans wrongful conviction for murder. No better example of how one movie can impact real life and effect actual change.
The Private Life of Sherlock Holmes (1970; dir. Billy Wilder) Even in its heavily edited theatrical release that hardly resembles the director's original intent, The Private Life of Sherlock Holmes is Billy Wilder's last great movie and the most underrated in his filmography. Wilder himself has expressed tremendous frustration and disappointment with how it turned out (and all the missing footage is gone forever, meaning we'll never get a true restoration), but he's selling the movie short -- it's still one of the best and most interesting takes on Sherlock Holmes ever put on film. It was hard to come by for years until MGM released a DVD in 2003; now it's on Instant and there's no excuse not to watch it. I promise you'll like it.