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The film begins with the following written statement: "Acknowledgment is hereby gratefully made to the United States Army and Air Force without whose cooperation, deep understanding, and sense of humor this picture could never been made." The "Sad Sack" comic strip was created by George Baker, then a sergeant in the U.S. Army, and made its debut in a May 1942 issue of the military weekly Yank, where it quickly became a permanent feature. It was so popular with servicemen and civilians alike that Simon and Schuster published two hardback collections of the strip. Following the end of World War II, the strip was picked up by the Bell Syndicate, which carried it in newspapers throughtout the U.S. until 1958.
In 1949, Baker signed an agreement with Harvey Comics to publish comic books featuring the "Sad Sack" character, who had been transformed into a civilian for his syndicated Sunday strip form. When the Korean War broke out, "Sad Sack" re-enlisted in the Army and gained even greater popularity, becoming one of the first comics to be published monthly. The "Sad Sack Comics" series continued until 1982, appearing in 287 issues. During World War II, "Sad Sack" had also been the basis for a short-lived radio show, which featured the voice of Mel Blanc.
According to a September 1950 Hollywood Reporter news item, producer Robert L. Lippert was planning a series of "Sad Sack" films, featuring actor Mickey Rooney. In January 1951, Los Angeles Times reported that Lippert was still negotiating for the film rights to "Sad Sack," and was considering actor Sterling Holloway for the lead role. By March 1951, however, Daily Variety announced that Paramount had purchased the film rights to Baker's character as a vehicle for Alan Young. Paramount press releases state that the planned Young picture was to be produced by Paul Jones.
According to modern sources, producer Hal Wallis acquired the film rights to Baker's comic character in hopes of making it into a Dean Martin-Jerry Lewis picture. Following the breakup of the comedy team, a January 7, 1957 Hollywood Reporter news item reported that Paramount, Hal Wallis Productions and York Productions (the production company owned by Martin and Lewis) had concluded an agreement in which Lewis was to appear in The Sad Sack for Wallis, with Martin agreeing to star in another film for the producer and studio later in 1957, as part of a settlement upon the unfulfilled portion of an earlier contract. Still hoping to reunite the duo, Wallis told Los Angeles Examiner at the time: "My arrangement still retains Martin and Lewis as a team for future Hal Wallis pictures." According to modern sources, The Sad Sack was one of two films-the 1965 picture Boeing, Boeing being the other-in which Lewis appeared to finish off his commitments to Wallis under the Martin-Lewis agreement with the producer.
According to Hollywood Reporter news items, portions of The Sad Sack were shot on location at Vincent Air Force Base near Yuma, AZ. Paramount press releases alos state that scenes were also shot at Fort MacArthur in San Pedro, CA. Technical advisor Lt. Doris Schmerling was the commander of the WAC troops stationed at Fort MacArthur, according to Hollywood Reporter. In 1962, Paramount re-released The Sad Sack, along with another 1957 Lewis film, The Delicate Delinquent, garnering $1,500,000 in North American rentals, according to New York Times.