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The Winner (1996)

Genres: Thriller, Comedy, Crime

A long lucky streak makes a nice guy the target of opportunists like his brother, his girlfriend, and some guys from New Jersey.

Rebecca De Mornay as Louise
Vincent D'Onofrio as Philip
Richard Edson as Frankie
Delroy Lindo as Kingman
Michael Madsen as Wolf
Saverio Guerra as Paulie
Billy Bob Thornton as Jack
Frank Whaley as Joey