This is one of Frank Sinatra's few post-From Here to Eternity (1953) movies in which he did not receive top billing, which surprisingly went to Rita Hayworth. Sinatra was, by that time, a bigger star, and his title role was predominant. When asked about the billing, Sinatra replied, "Ladies first." He was also quoted as saying that, as it was a Columbia film, Hayworth should have top billing because, "For years, she WAS Columbia Pictures", and that with regard to being billed "between" Hayworth and Kim Novak, "That's a sandwich I don't mind being stuck in the middle of." As Columbia's biggest star, Hayworth had been top billed in every film since Cover Girl (1944), but her tenure was soon to end with They Came to Cordura (1959).
Billy Wilder was the original choice to direct, with Mae West and Marlon Brando in the lead roles. He discussed it with Columbia studio head Harry Cohn over lunch one day. Not only did Cohn turn down him as director, but he later sent Wilder a bill for their lunch.
Columbia Pictures head Harry Cohn suggested Marlene Dietrich for the role of Vera Simpson. Dietrich turned down the part but suggested her friend Frank Sinatra for the role of Joey after Gene Kelly was denied the part. Cohn suggested Jack Lemmon before Sinatra was eventually cast.
Rita Hayworth plays the rich older woman keeping Frank Sinatra as her boy toy. In real life, Hayworth was only in her late 30s when she made this film and was three years younger than Sinatra.