Gone With the Wind (1939) winner of 8 Oscars at the 1940 Academy Awards:
Best Actress in a Leading Role: Vivien Leigh
Best Actress in a Supporting Role: Hattie McDaniel
Best Director: Victor Fleming
Best Writing, Screenplay: Sidney Howard (Posthumously. Sidney Howard became the first posthumous Oscar nominee and winner.)
Best Cinematography, Color: Ernest Haller, Ray Rennahan
Best Art Direction: Lyle R. Wheeler
Best Film Editing: Hal C. Kern, James E. Newcom
Best Picture
I recommend this movie with captions/subtitles due to the drawls and the fast-pace dialogue; the story sucks me in every time I start watching it, and the book is worth reading too. It's also neat to learn about the making of the film for the time; it's a classic for a reason.