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1950s

In 1950, Wilder co-wrote and directed the cynical noir comedy film Sunset Boulevard. It follows a reclusive silent film actress (Gloria Swanson), who dreams of a comeback with delusions of her greatness from a bygone era. She accompanies an aspiring screenwriter (William Holden), who becomes her gigolo partner. This critically acclaimed film was the final film Wilder collaborated with Brackett. The film was nominated for eleven Academy Awards; together Wilder and Brackett won the Academy Award for Best Original Screenplay.

In 1951, Wilder directed Ace in the Hole (a.k.a. The Big Carnival) starring Kirk Douglas in a tale of media exploitation of a caving accident. The idea had been pitched over the phone to Wilder's secretary by Victor Desny. Desny sued Wilder for breach of an implied contract in the California copyright case Wilder v Desny, ultimately receiving a settlement of $14,350. Although a critical and commercial failure at the time, its reputation has grown over the years. The following year, Wilder announced plans to direct and produce a film version of the Sophocles tragedy Oedipus Rex, adapted for the screen by Walter Reisch. They planned to shoot the film on location in Greece in Technicolor, but it never went into production.

Subsequently, Wilder directed three adaptations of Broadway plays, war drama Stalag 17, for which William Holden won the Best Actor Academy Award, romantic comedy Sabrina, for which Audrey Hepburn was nominated for Best Actress, and romantic comedy The Seven Year Itch, which features the iconic image of Marilyn Monroe standing on a subway grate as her white dress is blown upwards by a passing train. Wilder was nominated for the Academy Award for Best Director for the first two films and shared a nomination for Best Screenplay for the second. He was interested in doing a film with one of the classic slapstick comedy acts of the Hollywood Golden Age. He first considered, and rejected, a project to star Laurel and Hardy. He held discussions with Groucho Marx concerning a new Marx Brothers comedy, tentatively titled A Day at the U.N. The project was abandoned after Chico Marx died in 1961.

In 1957, three films Wilder directed were released: biopic The Spirit of St. Louis, starring James Stewart as Charles Lindbergh, romantic comedy Love In The Afternoon —Wilder's first screenplay with I. A. L. Diamond, who would become his regular partner—featuring Gary Cooper, Maurice Chevalier and Audrey Hepburn, and courtroom drama Witness for the Prosecution, featuring Tyrone Power, Marlene Dietrich and Charles Laughton. Wilder received an Academy Award nomination for Best Director for the last film.

In 1959, Wilder reunited with Monroe in the United Artists released Prohibition-era farce film Some Like It Hot. It was released, however, without a Production Code seal of approval, which was withheld due to the film's unabashed sexual comedy, including a central cross-dressing theme. Jack Lemmon and Tony Curtis played musicians disguised as women to escape pursuit by a Chicago gang. Curtis's character courts a singer (Monroe), while Lemmon is wooed by Joe E. Brown – setting up the film's final joke in which Lemmon reveals that his character is a man and Brown blandly replies "Well, nobody's perfect". A box office success, the film was lightly regarded by film critics during its original release, although it did receive six Academy Award nominations, including for Best Director and Best Screenplay. But its critical reputation grew prodigiously; in 2000, the American Film Institute selected it as the best American comedy ever made. In 2012, the British Film Institute decennial Sight and Sound poll of the world's film critics rated it as the 43rd best movie ever made, and the second-highest-ranking comedy.