In 2004 Houston, Jack Harris drives with several million dollars in a duffel bag to deliver to Russian mobsters, worried about the safety of his wife Diana and their children.
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Cosmo Vittelli, the proprietor of a sleazy, low-rent Hollywood cabaret, has a real affection for the women who strip in his peepshows and the staff who keep up his dingy establishment. He also has a major gambling problem that has gotten him in trouble before. When Cosmo loses big-time at an underground casino run by mobster Mort, he isn't able to pay up. Mort then offers Cosmo the chance to pay back his debt by knocking off a pesky, Mafia-protected bookie.
A shady lawyer attempts a Christmas Eve crime, hoping to swindle the local mob out of some money. But his partner, a strip club owner, might have different plans for the cash.
Chili Palmer is a Miami mobster who gets sent to L.A. to collect a bad debt from Harry Zimm, a Hollywood producer who specializes in cheesy horror films. When Chili meets Harry's leading lady, the romantic sparks fly. After pitching his own life story as a movie idea, Chili learns that being a mobster and being a Hollywood producer really aren't all that different.
'Sugar' Ray is the owner of an illegal casino and must contend with the pressure of vicious gangsters and corrupt police who want to see him go out of business. In the world of organised crime and police corruption in the 1920s, any dastardly trick is fair.