Plot: Philadelphia based Louis Winthorpe III was born into and has solely lived a life of privilege. He is Harvard educated, is successful at his job, has a lavish home paid for by his employers, and is wealthy. The children he will probably have with his fiancée Penelope will most likely also know nothing but privilege. But he and his friends, who all have similar backgrounds, are pompous and snobbish. His job is as managing director at Duke & Duke, a commodities brokerage house owned by brothers Randolph and Mortimer Duke. The Duke brothers often disagree with each other and make wagers on the outcome of these disagreements. Their latest wager is about "nature versus nurture": the importance environment plays versus one's natural bloodline in determining how one's life will turn out. The guinea pigs in their experiment are Winthorpe, whose life they will attempt to ruin to see how he reacts, and Billy Ray Valentine, a black hustler/crook who the Dukes and Winthorpe encountered in one of his scams. Like Winthorpe, Valentine was born into and has lived the only life he has ever known. They will attempt to place Valentine into every aspect of Winthorpe's life to see how he functions. Without either knowing of anyone else involved, Coleman, Winthorpe's manservant who is officially employed by the Dukes in his day-to-day job, and a streetwise hooker named Ophelia each play a role in the Duke's plan. Also deeply involved in their plan is a private detective the Dukes often use, Clarence Beeks. Beyond the outcome of the Dukes' experiment, can either Winthorpe or Valentine change the course of the new life set out for them by the Dukes, even if they knew what the Dukes were doing? Regardless, this experience will fundamentally change the lives of both Winthorpe and Valentine, but not at without the expense of others as well.
Alternative Plot: Upper-crust executive Louis Winthorpe III (Dan Aykroyd) and down-and-out hustler Billy Ray Valentine (Eddie Murphy) are the subjects of a bet by successful brokers Mortimer (Don Ameche) and Randolph Duke (Ralph Bellamy). An employee of the Dukes, Winthorpe is framed by the brothers for a crime he didn't commit, with the siblings then installing the street-smart Valentine in his position. When Winthorpe and Valentine uncover the scheme, they set out to turn the tables on the Dukes.
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