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I don't know if it would hold up completely, but how about something like The Player. My reasoning is that the whole movie is a movie about movies. It describes what makes a good movie as it seeks to apply its own advice. It also describes particular historical scenes. For instance it starts with a long single shot, while discussing the opening sequence of A Touch of Evil which is a very long complex tracking shot.
Mindwalk- Good example for dialog driven movies
Days of Heaven-Cinematography
Thin Blue Line (Faults in the justice systemin a particular case in Dallas Texas) and The Devil's Playground (about the Amish ritual that allows a teenager of sixteen to be free to experiment with secular culture for a few years before they commit to the church). StreetWise (follows several young teenagers who wander the streets in Seattle Washington) - Documentaries
Just a few.