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4. West Side Story (1961)

A scene from the Oscar-winning musical 'West Side Story'
West Side Story | United Artists

Stephen Sondheim’s modern musical retelling of Romeo and Juliet was sensational when it hit Broadway in 1957. And the film adaptation was a bonafide hit — especially with Oscar voters. West Side Story won 10 Oscars at the 34th Academy Awards, including nods for Sound, Music, Film Editing, Costume Design, Cinematography and Art Direction. It also took home four of the most coveted awards: Best Picture, Best Supporting Actor for George Chakiris, Best Supporting Actress for Rita Moreno, and Best Director for Robert Wise and Jerome Robbins.