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The working title of this film was Fair Weather. According to modern sources, the film was originally planned as a sequel to the 1949 M-G-M musical On the Town (see AFI Catalog of Feature Films, 1941-50), which starred Gene Kelly, Frank Sinatra and Jules Munshin as sailors on leave in New York City. However, Sinatra declined the assignment and Munshin was not available, so the sailors were changed to soldiers and the other two roles recast with dancers. Hollywood Reporter news items add Jack Santoro and Art La Forest to the cast, and report that June Foray recorded a character voice for the film. An August 1954 item in Hollywood Reporter's "Rambling Reporter" column stated that Janice Rule tested for a role. The participation of these actors in the final film has not been confirmed. Dan Dailey was borrowed from Twentieth-Century Fox for the production. Hal March, who portrayed boxer "Rocky Heldon," was the emcee on the popular CBS television quiz show The $64,000 Question, which debuted in June 1955.
The song "I Shouldn't Have Come" set special lyrics by Betty Comden and Adolph Green to Johann Strauss' "The Blue Danube." The song "I Like Myself" is performed while Kelly roller skates through the streets of New York. It's Always Fair Weather received Academy Award nominations for Best Story and Screenplay, and Best Scoring of a Musical Picture. The film marked the last directorial collaboration between Kelly and Stanley Donen. They had previously co-directed On the Town and the 1952 M-G-M film Singin' in the Rain . It's Always Fair Weather was also Donen's last film for M-G-M, and marked choreographer Michael Kidd's screen debut.