Once Upon a Time in Hollywood (2019)

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A love letter to the golden age of cinema, Quentin Tarantino’s Once Upon a Time in Hollywood pairs Brad Pitt with Leonardo DiCaprio in a sprawling tale of friendship, fading stardom, and Hollywood’s shifting tides in 1969.

Pitt’s role as stuntman Cliff Booth — cool, effortless, and mysterious — earned him the Academy Award for Best Supporting Actor. From sun-soaked streets of Los Angeles to a jaw-dropping alternate-history finale, Pitt’s laid-back yet magnetic performance steals the film, cementing Cliff Booth as one of his most beloved characters.