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Two CLASSICS!!! It's a really difficult decision with this one, but I gotta go with Cool Hand Luke because it really shows the psychologic disintegration of a man in a really negative environment. The scene where he eats fifty eggs and the scene where he keeps getting up after getting knocked down are classics. The Wizard of Oz is highly entertaining, but a bit more trivial. It doesn't make me think about life as much.
Cool Hand Luke. Paul Newman is just too much for Dorothy and the rest of Oz to handle.