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1987's "Wall Street" was released in theaters two months after Black Monday: the day the real stock market took a dive. In the timely film, Charlie Sheen plays Bud Fox, a young stockbroker who admires underhanded corporate raider Gordon Gekko (Michael Douglas). Bud pursues Gekko as a client with non-stop calls and contraband Cuban cigars, and when he finally makes contact, his entire life changes. Under the influence of Gekko, who famously utters the line "Greed, for lack of a better word, is good," Bud does some terrible things, including offering up insider information that could destroy his blue-collar father, played by Charlie Sheen's real-life dad, Martin Sheen.

The film, which won Douglas an Academy Award for Best Actor, was directed by Oliver Stone, who allowed the young actor to pick the person who would play his father in the film. He was given the choice between Jack Lemmon or...