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The film's opening titles are written as the camera pans a cartoon drawing of rural Vermont scenery, ending with a drawing of a dead body. According to a October 16, 1955 New York Times article, producer-director Alfred Hitchcock helped design the titles, which were drawn by New Yorker cartoonist Saul Steinberg. At the conclusion of the film, a title card reading "The trouble with Harry is over" appears, superimposed over a shot of Harry's corpse. Actor Philip Truex, who plays "Harry Worp," is seen in the film only as a dead body. Modern sources state that Hitchcock purchased the rights to Jack Trevor Story's novel anonymously, and upon learning the identity of the purchaser, Story and his agent were dismayed at having received only $11,000. According to information in the Paramount Scripts Collection, located at the AMPAS Library, Paramount originally considered purchasing Story's novel in 1950, just after it was published, but decided that its humor would be too difficult to translate to the screen.
Although a August 30, 1954 Hollywood Reporter news item stated that the picture would be shot in Maine and Connecticut, information in the Paramount Collection at the AMPAS Library reveals that the film was partially shot on location in Vermont in several locations, including Craftsbury, Stowe and Morrisville. Although Hitchcock had hoped to shoot the entire picture on location, inclement weather forced him to return to Paramount's Hollywood studios in mid-October 1954 and finish filming there. According to modern sources, Hitchcock changed the novel's London setting to Vermont in order to contrast the beauty of New England's brilliant autumn foliage with the dark comedic theme of the constant burial and exhumation of a corpse.
An April 1955 Daily Variety news item noted that the song "Flaggin' the Train to Tuscaloosa" was originally composed as a commercial jingle for the Lucky Strike Hit Parade televsion show. The news item noted that the melody originally had different lyrics when it was to be used for the commercial. A September 24, 1954 Hollywood Reporter news item includes Ramsay Hill in the cast, but he does not appear in the released picture. Hitchcock makes his customary cameo by walking past the limousine of the "millionaire" as he is admiring "Sam's" paintings at the roadside stand. A modern source states that Sam's paintings were created by artist John Ferren.
According to information in the film's file in the MPAA/PCA Collection at the AMPAS Library, the PCA office expressed reservations about the script because, as in the original novel, "Arnie" was illegitimate, as his father, Harry's brother, died before he could marry "Jennifer." After the screenplay was changed so that Arnie's legitimacy was clearly established, it was approved by the PCA. A December 1, 1954 studio billing sheet contained in the PCA file reveals that the opening title card was originally to read: "Alfred Hitchcock's Comedy About a Body The Trouble with Harry."
The picture marked the first collaboration between Hitchcock and composer Bernard Herrmann, who went on to compose numerous scores for Hitchcock, including those for Vertigo (see below) and Psycho. Considered one of the most important collaborations in the history of film music, Hitchcock and Herrmann worked together numerous times, with their final film being the Universal Pictures 1964 production Marnie (see AFI Catalog of Feature Films, 1961-70). The Trouble with Harry also marked the screen debut of Shirley MacLaine, who had been signed to a personal contract by Hal Wallis after he saw her perform in the Broadway production of Pajama Game, for which she was star Carol Haney's understudy. Wallis loaned her to Hitchcock's production company for The Trouble with Harry. MacLaine received mostly good notices for her film debut. Along with Kim Novak, MacLaine was named Most Promising Newcomer at the 1955 Golden Globes ceremony. According to studio records, Ernest Curt Bach, who played the chauffeur, was Edmund Gwenn's real-life valet. The Trouble with Harry marked the last American film of Gwenn, who died on September 6, 1959. Although Gwenn also appeared in the 1955 M-G-M production It's a Dog's Life, which was filmed after The Trouble with Harry, the Hitchcock production was released later. Gwenn's last film appearance was in the 1956 Italian-Spanish production Calabuch.
The film received a BAFTA nomination for Best Film from any Source, and MacLaine was nominated by BAFTA as Best Foreign Actress. Although the picture was not a financial success in the United States, it was well-received in Great Britain and France, and in an June 18, 1971 New York Times interview, Hitchcock stated that it was his favorite of all his films. According to a March 1984 LA Weekly article, Hitchcock so liked The Trouble with Harry that he required the writers who worked on the introductory segments for his television show to watch the film before writing his monologues.
According to a March 1963 New York Times article, Paramount intended to re-release The Trouble with Harry theatrically in a "Hitchcock package" with The Man Who Knew Too Much. As noted by modern sources, the rights to six films directed by Hitchcock, Rope, Rear Window, The Man Who Knew Too Much, Psycho, Vertigo and The Trouble with Harry, reverted to Hitchcock after their release. Although the director sold the rights to Psycho to MCA/Universal in 1962, he retained the rights to the five other films and by 1973, they were rarely in circulation because Hitchcock's lawyers were negotiating new financial arrangements for their distribution in theaters and on television. In July 1980, a New York Times article noted that due to Hitchcock's recent death, the films might soon become available again. In April 1983, the rights to the five films were sold to Universal, which re-released them theatrically as a special package in February 1984, with newly struck prints, and later on videocassette and on DVD.