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. An expansion on Anderson's 1993 short film Cigarettes & Coffee, it follows the bond between a senior gambler and a homeless man. It premiered at the 1996 Sundance Film Festival.

Plot

Sydney Brown, a well-dressed senior gambler, finds John Finnegan, a homeless man, forlornly sitting outside a diner in Sparks, Nevada. Sydney offers John a cigarette and buys him a cup of coffee. John tells Sydney that he went bust in Las Vegas and needs $6,000 for his mother's funeral. They travel to Vegas, where Sydney helps John win the money. Two years later, John becomes Sydney's protégé. Calm and reserved, Sydney displays a fatherly care for John, who is unsophisticated. John has a new friend named Jimmy, who does security work, and 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 John and her. Sydney asks John to show Clementine around town.