Bamboozled - Malcolm X is actually my favorite Spike Lee film, but I'm a fan of most of his movies. This is one I reserve for a more "intellectual" conversation to cite, since it deals with some pretty real issues about media portrayal of minorities, personal masquerades, etc. Somewhat preaching to the choir, but the execution is what matters. Deep film.
Clerks - Easily my favorite comedy. Comedy stemming from "real" situations, conversations, and such always get me more than slapstick comedy. I can quote, verbatim, big and small lines from at least 10 movies. This is one I pull from a lot. Plus, Kevin Smith and most of the cast are from Jersey. For such a ****ty reputation, there are a ton of people from Jersey in the entertainment industry.
The Exorcism of Emily Rose - This is a newer movie, but it's a rare, greatly executed, big release horror film. The courtroom stuff gives it a great dynamic, and hell, exorcism and possession make for interesting horror films. Underworld de-Anne Rice'd the vampire subgenre, but I would kill to see a vampire film on the level of this. Very well acted.
American Beauty - In a lot of ways, a good snapshot of pre-9/11 suburbia.
The Serpent & The Rainbow - Just an overlooked, interesting horror movie I suggest to folks. Has a voodoo slant, which I like, as I prefer religious horror to most slasher and exploitation films. Was going to put down Jacob's Ladder, but the crowd I hang with has mostly watched that.
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