While at the Sundance Feature Film Program, Anderson already had a deal with Rysher Entertainment to direct his first full-length feature, Sydney, retitled Hard Eight (1996). Upon completion of the film, Rysher re-edited it. Anderson, who still had the workprint of his original cut, submitted the film to the 1996 Cannes Film Festival, where it was accepted and screened in the Un Certain Regard section. Anderson managed to get his version released but only after he retitled the film, and raised the $200,000 necessary to finish it; Anderson and stars Philip Baker Hall, Gwyneth Paltrow and John C. Reilly contributed the funding. The version that was released was Anderson's and the acclaim from the film launched his career. The story concerns Sydney Brown (Hall), an experienced gambler who takes John Finnegan (Reilly) under his wing, while John becomes romantically involved with a troubled waitress (Paltrow). The film also featured Philip Seymour Hoffman as an arrogant gambler, beginning a five-film collaboration between the pair. In his review of the film, Chicago Sun-Times critic Roger Ebert wrote, "Movies like Hard Eight remind me of what original, compelling characters the movies can sometimes give us. "
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