★ = recommended, ♥ = personal favorite

You Can't Take It With You (1938) ♥

• starring Jean Arthur, Lionel Barrymore, James Stewart, Edward Arnold, Spring Byington
• directed by Frank Capra
• 126 minutes, black-and-white
• Won 2/7 Oscars, including Best Director
  • The first of three films that Frank Capra and James Stewart collaborated on.

Gone with the Wind (1939) ♥

• starring Clark Gable, Vivien Leigh, Leslie Howard, Olivia de Havilland, Hattie McDaniel
• directed by Victor Fleming
• 234-238 minutes, color
• Won 8/13 Oscars, including Best Actress (Leigh), Best Supporting Actress (McDaniel), Best Director, Best Screenplay and Best Cinematography (Color)
  • The first color film to win Best Picture.
  • Hattie McDaniel was the first African-American to be nominated for, and win, an Academy Award.

Rebecca (1940) ♥

• starring Laurence Olivier, Joan Fontaine, George Sanders, Judith Anderson
• directed by Alfred Hitchcock
• 130 minutes, black-and-white
• Won 2/11 Oscars, including Best Cinematography (Black-and-White)
  • The first film Alfred Hitchcock made in Hollywood, and his only film to win Best Picture.

How Green Was My Valley (1941)

• starring Walter Pidgeon, Maureen O'Hara, Anna Lee, Donald Crisp, Roddy McDowall, Sara Allgood
• directed by John Ford
• 118 minutes, black-and-white
• Won 5/10 Oscars, including Best Supporting Actor (Crisp), Best Director and Best Cinematography (Black-and-White)
  • This film beat Citizen Kane (often regarded as the greatest film of all time) when it won Best Picture.

Mrs. Miniver (1942) ★

• starring Greer Garson, Walter Pidgeon, Teresa Wright, Dame May Whitty, Henry Travers
• directed by William Wyler
• 133-134 minutes, black-and-white
• Won 6/12 Oscars, including Best Actress (Garson), Best Supporting Actress (Wright), Best Director, Best Screenplay and Best Cinematography (Black-and-White)
  • The first film to receive five acting nominations.
  • The first of two Academy Award Best Picture winners to receive nominations in all four acting categories.

Casablanca (1942) ♥

• starring Humphrey Bogart, Ingrid Bergman, Paul Henreid, Claude Rains
• directed by Michael Curtiz
• 102 minutes, black-and-white
• Won 3/8 Oscars, including Best Director and Best Screenplay

Going My Way (1944)

• starring Bing Crosby, Barry Fitzgerald
• directed by Leo McCarey
• 126-130 minutes, black-and-white
• Won 7/10 Oscars, including Best Actor (Crosby), Best Supporting Actor (Fitzgerald), Best Director, Best Screenplay and Best Music (Original Song)
  • Barry Fitzgerald was nominated for both Best Actor and Best Supporting Actor for the same performance, the only time this has ever happened. He won the Oscar in the supporting category but lost in the lead category to co-star Bing Crosby.

The Lost Weekend (1945) ♥

• starring Ray Milland, Jane Wyman
• directed by Billy Wilder
• 99-101 minutes, black-and-white
• Won 4/7 Oscars, including Best Actor (Milland), Best Director and Best Screenplay

The Best Years of Our Lives (1946) ♥

• starring Myrna Loy, Fredric March, Dana Andrews, Teresa Wright, Virginia Mayo, Harold Russell
• directed by William Wyler
• 172 minutes, black-and-white
• Won 7/8 Oscars, including Best Actor (March), Best Supporting Actor (Russell), Best Director and Best Screenplay

Gentleman's Agreement (1947)

• starring Gregory Peck, Dorothy McGuire, John Garfield, Celeste Holm, June Havoc, Anne Revere
• directed by Elia Kazan
• 118 minutes, black-and-white
• Won 3/8 Oscars, including Best Supporting Actress (Holm) and Best Director