The Apartment (1960)
d. Billy Wilder
Awards: 5
Nominations: 10

A dramatic comedy about an insurance clerk who advances by letting his scummy bosses meet with their mistresses at his apartment.

• the last entirely B/W Best Picture winner until Schindler's List (1993) (although it had some color sequences)
• none of the three nominated members of the acting cast (Lemmon, MacLaine, or Kruschen) of the Best Picture winner won an Oscar
• an unprecedented triple win for Wilder - three Oscars for co-writing, producing, and directing the same film

West Side Story (1961)
d. Jerome Robbins, Robert Wise
Awards: 10
Nominations: 11

Romeo and Juliet as a musical about warring white and Puerto Rican street gangs in New York City.

• the first of only two Best Picture winners to have more than one credited director (the co-directing team of Robbins and Wise) (see also 2007)
• Robbins was the only Best Director Oscar winner to win for the only film he ever directed
• the Best Picture-winner (a musical film) has the most Academy Award wins (10) of any other musical film, including Best Picture (there were other Best Pictures with more than 10 wins (i.e., Ben-Hur (1959), Titanic (1997), and The Lord of the Rings: The Return of the King (2003)), but they were not musicals)
• the next largest Best Picture-winning films would be Gigi (1958), The Last Emperor (1987) and The English Patient (1996), (coming close with 9 Oscars)

Lawrence of Arabia (1962)
d. David Lean
Awards: 7
Nominations: 10

A spectacular adventure about a British officer who found his place among Bedouin tribesmen in WWI Arabia.

• the only Best Picture winner to have credited roles for actors of only one gender
• beginning in 1962, the name for the top Oscar prize officially became Best Picture
• the first of four British-made films that won the top Best Picture Oscar in the decade of the 1960s. The other three were Tom Jones (1963), A Man For All Seasons (1966), and Oliver! (1968)
• arguably, it is the longest Best Picture nominee and winner - although Gone With the Wind (1939) comes close
• the film marked Sam Spiegel's third Oscar for Best Picture (earlier wins for the producer were for On The Waterfront (1954) and The Bridge On The River Kwai (1957)). Due to this Oscar win, Spiegel became (and remains) the only producer to have his name - and his name only - associated with three Best Picture Oscars.

Tom Jones (1963)
d. Tony Richardson
Awards: 4
Nominations: 10

The comic and amorous adventures of an eighteenth-century foundling, told with swinging sixties style.

• the only film in Academy history in which three actresses were nominated for the Best Supporting Actress Oscar (all lost)
• the only film in Academy history to receive five Oscar nominations for its acting performances - and then lose in all instances
• in the same year, the longest nominee for Best Picture, Cleopatra (1963) with a running time of just over four hours
• the next comedy film to win Best Picture was The Sting (1973), 10 years later

My Fair Lady (1964)
d. George Cukor
Awards: 8
Nominations: 12

George Bernard Shaw's Pygmalion reinvented as a musical about a flower girl taught to pass as a cultured duchess.

• with his win, Cukor became the oldest person to receive a Best Director award up to that time (surpassed in 2002)
• although Mary Poppins (1964) had 13 nominations (and five wins), it lost the Best Picture race
• all five titles of the Best Picture-nominated films referred to the film's characters (this also occurred in 2008)

The Sound of Music (1965)
d. Robert Wise
Awards: 5
Nominations: 10

The singing Von Trapp family and their governess, an aspiring nun, escape Nazi-occupied Austria.

• The Sound of Music topped Gone With The Wind (1939) as the most commercially-successful, money-grossing film to date - thereby saving its studio 20th Century Fox from bankruptcy
• the next Best Picture winner to not have its Screenplay nominated would be Titanic (1997)
• in the same year, Othello (1965) became the 3rd film in Academy history to receive four acting nominations without a Best Picture nomination (this also occurred in 1936, 1948, and 2008)

A Man For All Seasons (1966)
d. Fred Zinnemann
Awards: 6
Nominations: 8

A sixteenth-century chancellor pays dearly for defying King Henry VIII rather than betraying his religious principles.

• the film's win for Best Picture Oscar defeated another favored nominee Who's Afraid of Virginia Woolf? (1966) which earned 13 nominations (and won five, without winning Best Picture)
• the Best Picture winner faced stiff competition from Who's Afraid of Virginia Woolf? (1966), the only film in Academy history to be nominated in every eligible category; it was the first film to have its entire cast nominated for acting Oscars (also accomplished by Sleuth (1972) and Give 'Em Hell, Harry! (1975))

In the Heat of the Night (1967)
d. Norman Jewison
Awards: 5
Nominations: 7

An African-American cop from Philadelphia and a Mississippi police chief join forces to solve a murder.

• a celebrated, seminal, late 1960s film: the first - and only - mystery/detective film to win Best Picture, although it was really a hybrid crime-drama-thriller and civil-rights social issue film
• although Rod Steiger won the Best Actor Oscar, his major co-star Sidney Poitier didn't even receive a nomination, although his appearances in three popular films in 1967 made him a bona fide movie star (his other two films were To Sir, With Love (1967) and Guess Who's Coming to Dinner (1967)
• it was another surprise example of a nominated director (Norman Jewison) who failed to take home the Best Director Oscar - instead Mike Nichols won the award (presumably because he had failed to win as Best Director the previous year for Who's Afraid of Virginia Woolf? (1966))
• it was the first Best Picture Oscar winner to be adapted into a regular prime-time TV series (NBC: 1988-1992 and CBS: 1992-1995), with Carroll O'Connor as Sheriff Bill Gillespie and Howard Rollins as Virgil Tibbs

Oliver! (1968)
d. Carol Reed
Awards: 5
Nominations: 11

Charles Dickens' story of a plucky orphan scrambling to survive the mean streets of nineteenth-century London.

• the first film with an MPAA rating to win Best Picture
• to date, the first - and only - G-rated film to win Best Picture (although some pre-1968 Best Picture winners were rated G when re-released to theaters after 1968)
• the last musical film to win Best Picture until 34 years later (Chicago (2002)); there were five musical Best Picture winners between 1958 and 1968
• four of the ten Best Pictures in the 1960s were musicals (all based on previous Broadway hits)
• the Best Picture winner won five Oscars, and was also presented with a sixth Oscar, a special Academy Award for Choreography
• it would be 13 years until another British-made film would win Best Picture, Chariots of Fire (1981)
• in the same year, Russia's War and Peace (1968), the longest movie to ever win an Academy Award at 414 minutes, winner of Best Foreign Language Film

Midnight Cowboy (1969)
d. John Schlesinger
Awards: 3
Nominations: 7

A portrait of a naive hustler and a bottom-feeding con man living on New York's fringes.

• the only X-rated film to win the Best Picture Oscar, although the film was re-rated in the next decade to an R-rating
• in the same year, Anne of the Thousand Days (1969) and Butch Cassidy and the Sundance Kid (1969), the first M-rated films to be nominated for Best Picture
• in the same year, Sydney Pollack's They Shoot Horses, Don't They? (1969) received a remarkable nine nominations - but none of them were for Best Picture. It became the first (and only) film to receive the most nominations ever (9) without being nominated for Best Picture
• in the same year, Z (1969) was the first sub-titled film in Oscar history to be nominated for Best Picture; it was also the first film nominated as Best Foreign Language Film that also received a nomination for Best Picture; it won the Foreign Film Award, but not the Best Picture Oscar