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The working title of this film was Ah, Wilderness. The film is a musical version of Eugene O'Neill's play Ah, Wilderness!" and the 1935 M-G-M (non-musical) film version of his play, which was written by Frances Goodrich and Albert Hackett. Goodrich and Hackett, who were credited with the screenplay of the 1948 film, wrote only the screenplay of the 1935 version. The title of O'Neill's play was derived from a line in the poem "The Rubiyt of Omar Khayym." A January 1946 Hollywood Reporter news item notes that June Allyson and Ray McDonald were set to star in the film. Although Summer Holiday did not mark the motion picture debut of actress Anne Francis, it marked her first onscreen credit, which listed her as "Ann Francis." Francis' debut was in the 1947 M-G-M production This Time for Keeps (see below). Hollywood Reporter production charts indicate that Charles Schoenbaum replaced Charles Rosher as the director of photography approximately two weeks after the film went into production. Although a news item in Hollywood Reporter on July 10, 1946 indicated that film editor Albert Akst was being replaced by George White, Akst remained on the film. Some filming took place at Irvine Park and Busch Gardens near Pasadena, CA. According to a February 1948 Daily Variety news item, the final cost of the film was approximately $2,000,000. Modern sources note that production on the film was hampered by a two-week motion picture industry strike that began on June 22, 1946. During the strike, Mamoulian suspended full production on the film and used the time to rehearse scenes and pre-record musical numbers.
A biography of producer Arthur Freed credits Robert Tucker and Ralph Blane with the vocal arrangements, and notes that the song "Wish I Had a Braver Heart," sung by Gloria De Haven, was cut from the film before its release. Also cut from the picture was the first rendition of Walter Huston singing "Spring Isn't Everything." Although the film was completed in mid-October 1946, it was not released until May 1948. Modern sources note that the film's release was held up due to M-G-M's concerns that it would not do well at the box office. The picture lost nearly $1,500,000 in its initial release.
O'Neill's play was first produced by The Theatre Guild in New York in 1933 with George M. Cohan playing "Nat Miller." The role was subsequently played by Will Rogers and Harry Carey. In addition to the 1935 film version of O'Neill's play, which was directed by Clarence Brown and starred Wallace Beery, Lionel Barrymore, Aline MacMahon and Mickey Rooney, as "Tommy Miller," (see AFI Catalog of Feature Films, 1931-40; F3.0045), the play was presented in several television broadcasts, including a Celanese Theatre production, televised on ABC on October 3, 1951, which was directed by Alex Segal and starred Thomas Mitchell and Roddy McDowell; a Front Row Center production, televised on CBS on June 5, 1951, which was directed by Fletcher Markle and starred Leon Ames and Bobby Driscoll; and a Theatre in America Production, televised on PBS on October 13, 1976, which was directed by Arvin Brown and starred William Swetland and Richard Backus.