★ = recommended, ♥ = personal favorite

Gigi (1958)

• starring Leslie Caron, Louis Jourdan, Maurice Chevalier, Hermione Gingold
• directed by Vincente Minnelli
• 115 minutes, color
• Won 9/9 Oscars, including Best Director, Best Screenplay and Best Cinematography (Color)
  • The day after the movie won nine Oscars, M.G.M telephone operators were instructed to answer all phone calls with "Hello, M-Gigi-M."

Ben-Hur (1959) ★

• starring Charlton Heston, Jack Hawkins, Haya Harareet, Stephen Boyd, Hugh Griffith
• directed by William Wyler
• 212-222 minutes, color
• Won 11/12 Oscars, including Best Actor (Heston), Best Supporting Actor (Griffith), Best Director and Best Cinematography (Color)
  • This is the first of three films to win 11 Academy Awards, including Best Picture.

The Apartment (1960) ♥

• starring Jack Lemmon, Shirley MacLaine, Fred MacMurray, Jack Kruschen
• directed by Billy Wilder
• 125 minutes, black-and-white
• Won 5/10 Oscars, including Best Director and Best Screenplay
  • This was the last black-and-white film to win Best Picture until The Artist.

West Side Story (1961) ♥

• starring Natalie Wood, Richard Beymer, Rita Moreno, George Chakiris, Russ Tamblyn
• directed by Robert Wise, Jerome Robbins
• 152 minutes, color
• Won 10/11 Oscars, including Best Supporting Actor (Chakiris), Best Supporting Actress (Moreno), Best Director and Best Cinematography (Color)
  • The first film to win a Best Director Oscar for two directors.

Lawrence of Arabia (1962) ♥

• starring Peter O'Toole, Alec Guinness, Anthony Quinn, Jack Hawkins, Omar Sharif, José Ferrer, Anthony Quayle, Claude Rains, Arthur Kennedy
• directed by David Lean
• 216-227 minutes, color
• Won 7/10 Oscars, including Best Director and Best Cinematography (Color)

Tom Jones (1963)

• starring Albert Finney, Susannah York, Hugh Griffith, Edith Evans, Diane Cilento, Joyce Redman
• directed by Tony Richardson
• 128 minutes, color
• Won 4/10 Oscars, including Best Director and Best Screenplay

My Fair Lady (1964)

• starring Audrey Hepburn, Rex Harrison, Stanley Holloway, Wilfrid Hyde-White, Gladys Cooper, Jeremy Brett
• directed by George Cukor
• 170 minutes, color
• Won 8/12 Oscars, including Best Actor (Harrison), Best Director and Best Cinematography (Color)
  • When Rex Harrison accepted his Oscar, he dedicated it to his "two fair ladies," Audrey Hepburn and Julie Andrews, both who had played Eliza Doolittle with him on stage and screen.

The Sound of Music (1965) ♥

• starring Julie Andrews, Christopher Plummer, Eleanor Parker, Richard Haydn, Peggy Wood
• directed by Robert Wise
• 174 minutes, color
• Won 5/10 Oscars, including Best Director

A Man for All Seasons (1966)

• starring Paul Scofield, Wendy Hiller, Leo McKern, Robert Shaw, Orson Welles, Susannah York
• directed by Fred Zinnemann
• 120 minutes, color
• Won 6/8 Oscars, including Best Actor (Scofield), Best Director, Best Screenplay and Best Cinematography (Color)

In the Heat of the Night (1967) ♥

• starring Sidney Poitier, Rod Steiger, Warren Oates, Lee Grant
• directed by Norman Jewison
• 109 minutes, color
• Won 5/7 Oscars, including Best Actor (Steiger) and Best Screenplay