The Winner is a 1996 film directed by Alex Cox and written by Wendy Riss based on her play A Darker Purpose.
[1] Most noted for its quirky cast (Vincent D'Onofrio, Richard Edson, Michael Madsen, Billy Bob Thornton and Frank Whaley) and art department, including production designer Cecilia Montiel.
Not much caring if he wins or loses, Phillip goes on a weeks-long hot streak in Las Vegas that ultimately comes to the attention of a lot of people who want his money.
Lusting after it most is Louise, a lounge singer and con artist who seduces Phillip in the Liberace museum, then lies to him that she is $150,000 in debt from medical and funeral expenses for her parents.
Louise's current boyfriend Jack is another interested party, as is a loan shark, Kingman, and a mob hit man, Joey, who's perfectly willing to shoot innocent bystanders in the casino if it'll get him what he wants.