Leslie Howard

10

1939: The Greatest Year in Movie History

7

2/13: Gone With the Wind (1939) dir. Victor Fleming, starring: Vivien Leigh, Clark Gable, Leslie Howard, Olivia de Havilland, Hattie McDaniel

It received ten Academy Awards (eight competitive, two honorary) from thirteen nominations, including wins for Best Picture, Best Director, Best Adapted Screenplay, Best Actress, and Best Supporting Actress 

Hattie McDaniel (Best Supporting Actress) was the first African American to win an Academy Award.