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The film's working titles were Unconventional Linda and Vacation Bound. News items in Hollywood Reporter note that Joan Bennett was at one time cast as "Julia Seton" and Ginger Rogers was initially cast as "Linda Seton." Katharine Hepburn states in her autobiography that Columbia borrowed her from RKO for this production after she refused to play the lead in RKO's Mother Carey's Chickens . Hepburn, who had just been labeled "box office poison" by independent theater owners following a series of RKO flops, including her previous picture, Bringing Up Baby, left the studio shortly after this production. Modern sources add the following information about the production: Hepburn, who had been the understudy for the role of "Linda" in the Broadway play, had hoped to star in the earlier version of the film, and it was she who convinced studio head Harry Cohn to produce it for Columbia. She also requested George Cukor as director and Cary Grant for the role of "Johnny." Although both Donald Ogden Stewart and Sidney Buchman are credited with the screenplay, Cukor claimed that it was entirely Stewart's work. Stewart was one of playwright Philip Barry's best friends and had acted in the stage production of the play. Jean Dixon retired from the screen after this performance. Cukor tested Rita Hayworth for the role of the youngest sister. Art directors Steven Goosson and Lionel Banks were nominated for an Academy Award for their work on the picture.
Holiday was first filmed by Path in 1930, and starred Ann Harding and Mary Astor (see AFI Catalog of Feature Films, 1921-30; F2.2550). Edward Everett Horton was also featured as "Nick Potter" in that film. On June 15, 1978, a musical version of the play, titled Happy New Year, opened in New York, featuring sixteen Cole Porter songs.