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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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