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Max Fischer is a more than determined student at his prep school, Rushmore Academy where he oversees anything with the word “extra-curricular”. He befriends a preschool teacher named Ms. Cross, whom he ends up falling in love with. Only to find things take a turn for the worst when his mentor, Herman Blume, an unhappy millionaire falls for her as well. As a result, their personal and professional lives spiral out of control.

Upon his release from a mental hospital following a nervous breakdown, the directionless Anthony joins his friend Dignan, who seems far less sane than the former. Dignan has hatched a hair-brained scheme for an as-yet-unspecified crime spree that somehow involves his former boss, the (supposedly) legendary Mr. Henry. With the help of their pathetic neighbor and pal Bob, Anthony and Dignan pull a job and hit the road, where Anthony finds love with motel maid Inez. When our boys finally hook up with Mr. Henry, the ensuing escapade turns out to be far from what anyone expected.

Surfer/drifter/con man Jack Ryan (Wilson) makes his way to Hawaii and lands a job caring for an Walter Crewes (Freeman), a judge on the island. His new gig leads to an involvement with an beautiful, enterprising woman (Foster), who’s really the lover of a real estate tycoon (Sinise) - a shady businessman and longtime rival of Judge Crewes. Ryan, naturally, has to choose between the woman, the money, or the honorable path.