This is not a pretentious list. You won't see French New Wave or so-and-so's-student-film-before-they-got-famous here.
  1. Once Were Warriors
    From New Zealand, it follows a Maori family's dealings with tradition/culture, abuse, alcohol... It's heartbreakingly good.
  2. Death in Venice
    An interesting story of a man who was obsessed with a beautiful boy on vacation in Venice. The music is indulgent.
  3. The Color Purple
    This film is proof that white people don't watch movies with black people in it. I showed an excerpt of this film in grad school to a class full of media majors and no one but my professor had seen this Spielberg-directed, epic, sad, funny, inspiring piece of work.
  4. American Movie
    It's a documentary about a filmmaker, but it so goes outside of the demographic that knows about it. It's freaking hilarious and the main character is kind of an Everyman in that he struggles to achieve his life goal with many setbacks.
  5. Cinderella
    The one with Brandy and Whitney Houston. It's very cheesy. But that's a good thing here!
  6. Norman
    A teenage boy pretending to have cancer in order to make it through his day to day. Angsty but really good.
    Suggested by   @eclecticmouse