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Paul Thomas Anderson disliked the title Hard Eight because it was imposed by the studio, Rysher Entertainment, against his wishes. His original title was Sydney, which he felt accurately reflected the film as a character study of the protagonist, Sydney (Philip Baker Hall). Anderson derided Hard Eight as a "TV movie" title that genericized the film into a gambling thriller. The studio, conversely, argued that Sydney was a poor marketing hook and feared audiences would confuse it with the city in Australia. Anderson eventually accepted the title Hard Eight as a compromise to ensure the release of his preferred director's cut.
Paul Thomas Anderson strongly disliked the title Hard Eight primarily because it was applied against his wishes by the studio/distributor (Rysher Entertainment), and he felt it misrepresented the film's core identity.
Here are the specific details of his objection:
A specific, frequently cited reason for the studio's rejection of the title 'Sydney' was their fear that audiences would mistake it for a movie about the Australian city. Anderson has mocked this reasoning in interviews.
While Anderson fought for his cut of the film, he ultimately conceded the title 'Hard Eight' as part of the deal to get his version released.