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During the opening credits, while singing "Life Could Not Better Be", Danny Kaye constantly pushes Basil Rathbone's re-appearing credit off the screen. The Court Jester was the second film by Dena Enterprises, a film production company owned by actor Danny Kaye and his wife, songwriter Sylvia Fine. In partnership with writer-producer-directors Melvin Frank and Norman Panama, Dena Productions had previously filmed another Danny Kaye comedy, Knock on Wood, a 1954 Paramount release . Though Hollywood Reporter news items report a production starting date of July 1954, The Court Jester did not begin filming until late Nov. At that time, New York Times reported that the picture's budget had been set at $3,000,000, with its two main sets-the castle interior and its courtyard-having been built on two separate Paramount sound stages at the cost of over $200,000.
According to the file on the film in the Paramount Collection at the AMPAS Library, The Court Jester was originally given a production budget of $2,487,000, with a forty-eight day shooting schedule. After the first week of filming, cinematographer Ray Rennahan was dismissed from the production and replaced by the credited director of photography, Ray June. After filming for nearly three months, The Court Jester temporarily shut down production on February 16, 1955, then resumed on February 25, 1955 and finished its initial shooting on March 12, 1955. The production was reopened and closed for a single day-March 18, 1955 -for additional cuts and retakes.
According to a October 29, 1955 Paramount breakdown of the film's expenses, The Court Jester's total cost to that point was $3,702,103, having used seventy-six actual days for filming, eighteen days of rehearsal, and another eighteen days for second unit work, including location shooting in Palos Verdes, CA. In its January 1956 feature article on the film, Life stated that The Court Jester was the most expensive film comedy produced to date.
According to Hollywood Reporter, the extended shooting on The Court Jester almost cost Glynis Johns a featured role in the 1955 Boulting Bros. production Josephine and the Men, as the start date on that film conflicted with The Court Jester's extended schedule. The scheduling was worked out, however, and the actress did appear in the British film. According to the file on the film in the MPAA/PCA Collection at the AMPAS Library, there were two Sammy Cahn-Sylvia Fine songs-"Pass the Basket" and "Where Walks My True Love"-that were approved for use in The Court Jester, but were not performed in the released film. Also, the original title for Fine's composition "The Maladjusted Jester" was "The Court Jester's Lament."
In his review of The Court Jester, Hollywood Reporter critic Jack C. Moffitt claimed that the hypnosis joke, in which Kaye changes from swashbuckler to fool and back at the snap of Mildred Natwick's fingers, was stolen from him. Calling the supposed plagiarism "a feeling of flattered nostalgia," Moffitt stated that he had originally written a similar scene for the 1937 Paramount film Mountain Music (see AFI Catalog of Feature Films, 1931-40) in which Bob Burns falls in and out of love with Martha Raye each time he is hit on the head. Moffitt did admit in his review, however, that he had stolen the comic piece himself from Charlie Chapin's 1931 classic City Lights, which contains a sequence in which millionaire Harry Myer loves Chaplin when he is drunk, but despises the little tramp when sober (see AFI Catalog of Feature Films, 1931-40). Moffitt also went to lengths to point out that the famous "The pellet with the poison is in the chalice from the palace, while in the vessel with the pestle has the brew that is true" sequence in The Court Jester was a "shortened version" of the old Bob Hope tongue-twister routine: "There's a nick on the muzzle of the pistol with the bullet and a scratch on the barrel of the pistol with a blank."
Hollywood Reporter production charts and news items include Marilyn Watson, James Robertson, Joe Ploski, Ethan Laidlaw and George Ford in the cast, but their appearance in the released film has not been confirmed. According to modern sources, Kaye was trained for his fencing scenes by U.S. Olympic coach Ralph Faulkner. Kaye received a Golden Globe nomination for Best Performance by an Actor, Musical or Comedy for his work in the film. Soon after concluding filming on The Court Jester, Paramount released the Danny Kaye short subject Assignment Children, a documentary for the United Nations Children's Fund, for which Kay was Ambassador-at-Large. In June 1966, The Court Jester was selected to open the Film Society of Lincoln Center's Danny Kaye Festival, with its opening night fund raiser held on behalf of UNICEF's 50th anniversary. Kaye had acted as the special ambassador for the United Nation's children's organization during its first thirty-four years.