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The working title of this film was The Gay Girls. According to a January 1954 Los Angeles Times news item, Judy Holliday was under consideration to star in the picture, which was baased on the same source as My Sister Eileen, a 1942 Columbia release, also titled My Sister Eileen (see AFI Catalog of Feature Films, 1941-50). The film was the first onscreen choreography credit for Bob Fosse, and is the only time he is listed as "Robert Fosse."
Ruth McKenney's stories, on which Joseph Fields and Jerome Chodorov based their play, were originally published in The New Yorker magazine. According to news items in both Daily Variety and Los Angeles Times, in October 1955 Columbia was sued by playwrights Fields and Chodorov for six million dollars, alleging that Columbia violated the 1941 contract under which the studio purchased the films rights, which stipulated that the studio "shall not have the right to produce any 'sequels.'" The playwrights argued that because the 1955 film was a musical, with altered characters, and new situations, it was not a legitimate remake, but a sequel. A May 1958 Hollywood Reporter news item indicates that the suit was settled out of court just prior to the trial. In December 1955 author McKenney also filed suit against Columbia, claiming sole and exclusive ownership of the book and magazine articles upon which My Sister Eileen was based and demanding an accounting of the film's profits as well as a restraint on further release of the films. The final outcome of this suit is not known.
Richard Quine, who directed the 1955 film, portrayed "Frank Lippencott" in the 1942 Columbia production of the play, which co-starred Rosalind Russell and Janet Blair, and was directed by Alexander Hall. A Broadway musical, Wonderful Town (New York, 25 February 1953), which also starred Russell, was also based on the Fields and Chodorov play as was the December 2, 1958 CBS television production Wonderful Town, which again starred Russell, with Jacqueline McKeever and was directed by Mel Ferber. From October 5, 1960 to April 12, 1961, CBS broadcast a half-hour television series titled My Sister Eileen, starring Elaine Stritch and Shirley Bonne and directed by Oscar Rudolph.