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The film's working title was All My Tomorrows. According to various contemporary news items, the play went through a number of transformations before opening on Broadway: Arthur Schulman first wrote it in a playwriting course as a one-act piece entitled "The Dragon's Head" in the late 1940s, and later expanded it to a full-length play entitled My Fiddle Has Three Strings, which was tried out in Westport, CT in 1949. He then wrote a new version, which was never produced, and rewrote it as a television play which ran on Playwright's '56.
When Garson Kanin expressed an interest in producing the play, Schulman revised it again, and it opened on Broadway as A Hole in the Head in February 1957, starring Paul Douglas. After a preview of the film, Schulman wrote a novelization of the story, which, he said, contained material not found in any previous version. According to news items and information in the press book on the film, Frank Sinatra saw the play on Broadway and in 1957 paid a reported $200,000 to the author for the screen rights. Sinatra hired Schulman to write the screenplay, then contacted Frank Capra, who agreed to direct.
According to Capra's autobiography, with a handshake, Sinatra and Capra formed SinCap Productions in which he held one-third interest, while Sinatra retained two-thirds. Because of Sinatra's previous commitments, production was not scheduled until late 1958. According to his autobiography, Capra, in the meantime, planned to make a film for Columbia Pictures, but when Columbia president Harry Cohn died, the project was cancelled. As noted in several reviews, A Hole in the Head was Capra's first feature film since his 1951 Paramount release Here Comes the Groom.
According to news items and the film's press book, after having seen Eddie Hodges on the television quiz show Name That Tune, Capra introduced the young actor, who was then appearing in The Music Man on Broadway, to Sinatra, and they agreed to hire him. A Hole in the Head marked Hodges' feature-film debut. Connie Sawyer, in her screen debut, reprised her role as "Miss Wexler" from the Broadway production. The character of "Jerry Marks" was newly created for the film. As noted in some reviews, the principal characters, who were Jewish in the play, had been changed to Italian Americans in the film. The Los Angeles Times reviewer commented that the change seemed to be "more of a loss than a gain. As it is, Edward G. Robinson, called Mario Manetta... makes little effort to disguise the ethnically Jewish humor of the character originally known as Max."
Much of the filming was done in locations at Miami Beach, including the Fontainebleau Hotel, West Flagler Dog Track, the Cardozo Hotel, which doubled for the fictional "Garden of Eden" hotel, and the South Beach oceanfront area. The company also had one day of shooting at Hollywood Beach near Oxnard, CA. Interiors were shot at the Samuel Goldwyn Studios, and after most of the crew returned to California from Florida, a second unit remained in Miami Beach to shoot the opening credit sequence, which has the cast names preceding the title, as well as the title, in letters connected to 300 feet of netting pulled by the Goodyear blimp.
According to the film's press book, director of photography William Daniels used the new high-speed Panatar lens developed by Panavision for color photography, which allowed outdoor night scenes to be shot with one-tenth the lighting that was normally required. According to a news item in Variety, shooting in Miami occasioned two lawsuits against the producing company, and filming, which was supposed to take three to four weeks in Miami Beach, was stopped after an aborted two weeks. Hollywood Citizen-News notes that the party scene at the Fontainebleau Hotel included water skiers from Cypress Gardens, two orchestras, wild birds and "some 85 beauties, most of them hired locally."
The film contains a gag Capra used in The Strong Man, starring Harry Langdon, which he directed in 1927 (see AFI Catalog of Feature Films, 1921-30). In both films, the protagonist carries a woman up a flight of stairs while walking backward and without realizing it continues climbing up the steps of a ladder before falling. The song "High Hopes" won the Academy Award for Best Song. On June 10, 1959, just prior to the release of A Hole in the Head, Capra appeared as the honoree on Ralph Edwards' popular television biography program This Is Your Life.
According to Capra's autobiography, problems on the set occurred because he found that Sinatra's acting suffered from repeated rehearsals, while Robinson needed them. Although at first Robinson resented Capra's insistence that they film without rehearsals, Robinson soon accepted the situation and gave a performance which Daily Variety called "the comedy stand-out of the film."
Although in the late 1950s the South Beach area of Miami, where the film was set, was overshadowed by the more glamorous areas surrounding large hotels like the Fontainebleau, beginning in the mid-1980s the South Beach was revitalized. The 1939, art deco Cardozo Hotel, which appeared as the Garden of Eden in the picture, was completely renovated and subsequently reopened as a small, luxury hotel, in keeping with the now trendy South Beach neighborhood in which it is located. The "Florida Disneyland" that "Tony Manetta" dreams of building in the film, eventually became Disney World, which opened near Orlando, FL in October 1971.