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 Louis Winthorpe is a businessman who works for commodities brokerage firm of Duke and Duke owned by the brothers Mortimer and Randolph Duke. Now they bicker over the most trivial of matters and what they are bickering about is whether its a persons environment or heredity that determines how well they will do in life. When Winthorpe bumps into Billy Ray Valentine, a street hustler and assumes he is trying to rob him, he has him arrested. Upon seeing how different the two men are, the brothers decide to make a wager as to what would happen if Winthorpe loses his job, his home and is shunned by everyone he knows and if Valentine was given Winthorpes job. So they proceed to have Winthorpe arrested and to be placed in a compromising position in front of his girlfriend. So all he has to rely on is the hooker who was hired to ruin him.
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 ones natural bloodline in determining how ones 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 Winthorpes life to see how he functions. Without either knowing of anyone else involved, Coleman, Winthorpes 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 Dukes 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.
		 Eddie Murphy 
 Billy Ray Valentine
		 Dan Aykroyd 
 Louis Winthorpe III
		 Ralph Bellamy 
 Randolph Duke
		 Don Ameche 
 Mortimer Duke
		 Denholm Elliott 
 Coleman
		 Maurice Woods 
 Duke & Duke Employee
		 Richard D. Fisher Jr. 
 Duke & Duke Employee
		 Jim Gallagher 
 Duke & Duke Employee
		 Anthony DiSabatino 
 Duke & Duke Employee
		 Bonnie Behrend 
 Duke & Duke Employee
		 Sunnie Merrill 
 Duke & Duke Employee
		 James Newell 
 Duke & Duke Employee
		 Mary St. John 
 Duke & Duke Employee
		 Bonnie Tremena 
 Duke & Duke Employee
		 David Schwartz 
 Duke & Duke Employee
		 Tom Degidon 
 Duke Domestic
		 William Magerman 
 Duke Domestic
		 Alan Dellay 
 Duke Domestic
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