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The working title of this film was The Glad Game. David Swift's onscreen credit reads: "Written for the screen and directed by." Although Hayley Mills is listed last in the closing credits, her name appears after Kevin Corcoran's in the opening credits. According to a February 16, 1959 Publishers Weekly news item, Walt Disney purchased the screen rights to Eleanor H. Porter's best-selling novel Pollyanna and its sequel, Pollyanna Grows Up, in order to make a film based on both stories. However, the final film was based only on the first book. Prior to its publication in book form, Pollyanna was serialized in Christian Herald Magazine in 1912. As noted in an August 1959 New York Times article, the film's story was close to its source, but changed the manner in which "Pollyanna" breaks her legs, and "simmered her cheerfulness down."
Thirteen-year-old Hayley Mills, the daughter of actor John Mills, made her American feature film debut in Pollyanna. She had earlier appeared in the British film Tiger Bay. She went on to star in such classic films as Disney's The Parent Trap (1961, also directed by Swift) and the 1966 Columbia release The Trouble with Angels (directed by Ida Lupino; for both, see AFI Catalog of Feature Films, 1961-70). Accounts vary slightly as to how Disney cast Mills in Pollyana. He chose her for the role after casting her father for a role in Swiss Family Robinson (see below), and a August 30, 1959 New York Times article stated that, while watching Tiger Bay to assess John's performance, the producer was impressed by the girl's performance in the same film; studio press materials, however, claimed that Disney first considered Hayley after meeting her in person with her family at Disneyland.
Press materials add the following information: The film was shot mostly on location in Santa Rosa and Napa, CA. Locations included the St. Helena railroad station, the Napa River, Stag's Leap winery, Luer Ranch and the Egan Ranch, owned by the uncle of Richard Egan, who played "Dr. Edmund Chilton" in the film. "Aunt Polly's" house, now called Mabelton House, belonged to Mrs. Juilliard McDonald, a member of the famed Juilliard musical family. The crew planted the tree that Pollyanna climbs in the already tree-filled McDonald yard, so that it could then be moved to the studio sound stage for matching shots. Hundreds of local extras were used for crowd scenes, and the production augmented the then-drought-stricken Napa River with 20,000 gallons of water, which were later used to irrigate a local alfalfa ranch.
A August 24, 1959 Hollywood Reporter news item states that the crew shot for two days at the Warner Ranch before returning to Disney's Burbank studio. There, according to press materials, the Aunt Polly set, measuring 110 x 90 feet, consisted of six full rooms that were interconnected in order to allow the cameramen to move continuously from one room to another without having to stop shooting. Although Time listed the film's final budget at $3.2 million, modern sources estimate it at $2.5 million. The film marked Swift's writing and directing debut.
Upon its release, the film garnered glowing reviews. The Variety review stated that "Miss Mills seems headed toward a great career." The Hollywood Reporter reviewer commented that the film "should precipitate a wholesale desertion of that box in the living room, if the addicts haven't lost their means of locomotion," and called Mills an "exceptional talent." For this role, Mills was awarded a special 1960 Academy Award for the Most Outstanding Juvenile Performance, marking the the last time the special award was given. Pollyanna won the Federation of Motion Picture Councils' award for the Best Family Picture of 1960.
A previous version of Porter's novel had been filmed in 1920 by United Artists, entitled Pollyanna, directed by Paul Powell and starring Mary Pickford (see AFI Catalog of Feature Films, 1911-20). The Disney version aired on the Walt Disney Presents television show in three parts on 1, 8 and December 15, 1963.