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Before splitting, apparently without rancour, Brackett and Wilder collaborated on one more film, which may have been their best. Sunset Boulevard (1950) was the caustic tale of an out-of-work screenwriter (William Holden) who agrees to move in with former silent-film star Norma Desmond (Gloria Swanson), an eccentric recluse who wants him to write her comeback vehicle. The story is narrated by the writer’s corpse, which is seen floating facedown in a swimming pool in the film’s indelible opening scene. Wilder and Brackett’s storytelling prowess is on full display in what many critics consider to be the ultimate Hollywood story. Holden gave the first important performance of his career as the kept writer who despises himself for his willingness to sell out even as he pities his self-deluded benefactress. Also notable is director Erich von Stroheim’s portrayal of Norma’s butler, ex-husband, and former director. (Von Stroheim actually directed Swanson in the uncompleted silent Queen Kelly, a segment of which is shown in Sunset Boulevard.) Swanson’s deliberately over-the-top performance as the tragic Norma earned her an Academy Award nomination as best actress. Wilder and the film were also nominated for Academy Awards; the screenplay by Wilder, Brackett, and D.M. Marshman, Jr., won.

Ace in the Hole (originally titled The Big Carnival; 1951) was Wilder’s first endeavour as both producer and director, and it would prove to be his first box-office failure. This acerbic drama, a corrosive account of a tabloid reporter (Kirk Douglas) who amorally manipulates a mining tragedy in New Mexico to artificially extend its run on the front pages, was viewed by some critics as heavy-handed. Nevertheless, its screenplay (by Wilder, Lesser Samuels, and Walter Newman) was nominated for an Academy Award.

Stalag 17 (1953) was far more successful on every front. It was based on a Broadway play about the dynamics of a German prisoner-of-war camp during World War II that had been written by two former internees and starred Holden as a clever but reviled bunkhouse entrepreneur who is accused of having leaked information to the camp commandant (Otto Preminger). The black humour and suspense are adroitly handled by Wilder, who again was nominated for an Academy Award, but the focus is firmly on Holden, who delivered an Academy Award-winning performance (best actor).

Samuel Taylor’s play Sabrina Fair provided the source material for the May-December romantic comedy Sabrina (1954), a box-office hit that left some critics disappointed by its lack of Wilder’s characteristic acerbic bite. Holden and Humphrey Bogart portrayed a pair of wealthy brothers with inimical lifestyles who both fall for their chauffeur’s daughter (Audrey Hepburn) when she returns from a Continental makeover. Wilder, Hepburn, and the screenplay were all nominated for Academy Awards.

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The screenplay for The Seven Year Itch (1955) was a collaboration between Wilder and George Axelrod, the author of the play on which the film was based. Tom Ewell, reprising the role he had played onstage, starred as a middle-aged Manhattan book-publishing executive whose wife and son are away for the summer, leaving him free to fantasize about his seductive new upstairs neighbour (Marilyn Monroe at the peak of her popularity as a sex symbol). Wilder’s next project, The Spirit of St. Louis (1957), would be the only biographical film that he would ever make. James Stewart played famed aviator Charles Lindbergh, whose 1927 New York-to-Paris solo flight is the centrepiece around which Wilder constructed a first-rate story.

With Love in the Afternoon (1957), Wilder began working with a new writing partner, I.A.L. Diamond, though this first collaboration between them is generally held to be one of their lesser efforts. This homage to Lubitsch’s sophisticated comedies, based on the novel Ariane by Claude Anet, featured an aging Gary Cooper as an American playboy living in Paris who becomes infatuated with a young cellist (Hepburn) and unwittingly hires her private-eye father (Maurice Chevalier) to investigate her.

Wilder’s third film of the year, Witness for the Prosecution (1957), was a brilliantly structured courtroom drama based on a long-running play by Agatha Christie. Tyrone Power played a murder suspect who persuades an ailing but able barrister (Charles Laughton) to defend him. The defendant’s loyal but inscrutable wife (Dietrich, in a film-stealing performance) is his only alibi, and the plot turns on her flip-flopping testimony. Laughton (best actor), Elsa Lanchester (best supporting actress), Wilder (best director), and the film itself were all nominated for Academy Awards.

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Wilder’s next film, Some Like It Hot (1959), not only was one of the decade’s most accomplished comedies but came to be regarded as among the best comedies in the history of American film. This riotous sex farce (written with Diamond) starred Jack Lemmon and Tony Curtis as Chicago musicians on the run from Prohibition-era gangsters after accidentally witnessing the St. Valentine’s Day Massacre. Joe (Curtis) and Jerry (Lemmon) don women’s clothes to join an all-woman band bound for a performance in Florida. The rest of the film alternates between Joe’s efforts to woo the band’s luscious but vulnerable singer (Monroe) while disguised as a yachtsman and Jerry’s gradual surrender to his feminine side. Some Like It Hot was a box-office smash, the biggest hit of Monroe’s career, and earned Lemmon an Academy Award nomination for best actor, Wilder yet another nomination for best director, and Wilder and Diamond a nomination for best screenplay.