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Hard Eight (originally titled Sydney) is a 1996 American crime film written and directed by Paul Thomas Anderson in his feature directorial debut, and starring Philip Baker Hall, John C. Reilly, Gwyneth Paltrow and Samuel L. Jackson. It is the expansion of the short film Cigarettes & Coffee. The film follows the life of a senior gambler and a homeless man. It premiered at the 1996 Cannes Film Festival.

Plot

Sydney Brown, a well-dressed senior gambler, finds John Finnegan, a homeless man, forlornly sitting outside a diner in Sparks, Nevada. He offers him a cigarette and buys him a cup of coffee. John tells Sydney that he lost his money in Las Vegas and he needs $6,000 for his mother's funeral. Sydney offers to drive John to Vegas, where he helps John win the money. Two years later, John has become Sydney's protégé. Sydney is calm and reserved and displays a fatherly care for John, who is unsophisticated. John has a new friend named Jimmy, who does security work. John is attracted to Clementine, a cocktail waitress in Reno. Sydney meets Clementine, and learns that she moonlights as a prostitute. Although Clementine believes Sydney might want to use her services, he wants to build a connection between her and John. Sydney asks John to show Clementine around the town.