Tough question. Off the top of my head I would say; The 25th hour by Spike Lee, The Spanish Prisoner by David Mamet, If These Walls Could Talk by a Variety of extremely talented female directors including Cher. I think the film was produced by the incomparable Nancy Savoca; I will need confirmation on that one. IMHO the film should be mandatory viewing for all H.S students. The Last Waltz by Martin Scorsesee, Magnolia by Paul Thomas Anderson.
Generally anything produced or directed by Paul Thomas Anderson, Marty Scorsesee, Frank Copolla (I also like his wine) Stanley Kubrick and Spike Lee.
Super Troopers is one of the funniest movies I ever saw. Meow.