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The late 1938 release of Carefree represented the longest gap between RKO's Fred Astaire/Ginger Rogers pictures and signalled the beginning of the end of their cinematic collaboration. Prior to making Carefree, Astaire made A Damsel in Distress without Rogers, while Rogers made Having Wonderful Time, Stage Door and Vivacious Lady without Astaire. Although Carefree received somewhat mixed reviews, Motion Picture Herald's William R. Weaver called it the "greatest Astaire-Rogers picture." Luella Gear, who had played "Hortense" in the stage version of The Gay Divorce, made her screen debut in the film. RKO borrowed Ralph Bellamy from Columbia for the picture. According to a Hollywood Reporter news item, Dave Dreyer, the head of RKO's music department, signed Ray Hendricks to sing Irving Berlin's "The Night Is Filled with Music" in the film. The number was dropped from the production, however, and the music is only heard as background filler. Hollywood Reporter production charts add William Corson to the cast, but his participation in the final film has not been confirmed. According to modern sources, Grace Hayle's part was cut from the film. The Variety reviewer noted that Robert Mitchell and the St. Brendan's Boys, popular Los Angeles radio performers, were edited out the picture as well. Location shooting was done at the Columbia Ranch and at Busch Gardens in Pasadena. Carefree was nominated for three Academy Awards: Van Nest Polglase and Carroll Clark for Best Art Direction, Victor Baravalle for Best Musical Score, and Irving Berlin for Best Song ("Change Partners").
Unlike the dances in previous Astaire-Rogers' films, the dances in Carefree, particularly the one performed to "I Used to Be Color Blind," used many lifts. In his autobiography, Astaire relates the following information about the production and the RKO series: "Pan[dro] Berman had already scheduled The Story of Vernon and Irene Castle to follow Carefree and that was to be the last of the series....I think we had as much fun with 'The Yam' as any number we ever did together. It was not exactly a dance for popular ballroom use but it made a good screen gimmick. 'I Used to Be Color Blind' was another one. We dreamed up a dream dance for that, partly in slow motion.... When we shot the dance for slow motion it of course was danced in normal fashion. But the special camera for that sort of thing sizzles away at four times faster speed, so that when the film is run normally, the action moves four times slower....For several years I had been planning a golf dance solo but could not find a suitable spot for it until Carefree came along. Fooling around at Bel Air one day, I did a few impromptu rhythm steps just before hitting one off the tee and was surprised to find that I could really connect that way....When I mentioned it to [director] Mark Sandrich for this story, he told me he thought it could be written in, but he wanted me to demonstrate what I had in mind. I took him to the practice tee at Bel Air....He approved. The next step was to set up a private driving range at the RKO ranch for rehearsals. I had about three hundred golf balls and five men shagging them, a piano and Hal Borne to play for me....This went on for two weeks...." Studio production files indicate that that sequence was shot from 14-15 April 1938, three weeks prior to the start of principal photography. Modern sources note that during the shoot, Astaire performed to Borne's piano accompaniment, and that orchestral sound was added in post-production.
Modern sources add the following information about the production: With the exception of "Change Partners," Berlin wrote the entire score for Carefree in a few days while on vacation in Phoenix, AZ. Berlin wrote "Change Partners" for Astaire and Rogers years before Carefree was produced. In addition to the omission of "The Night Is Filled with Music," a second dream sequence, which featured the Berlin song "Let's Make the Most of Our Dream," was filmed but deleted from the final picture. For the "I Used to Be Color Blind" sequence, which Berlin wrote with Technicolor in mind, color tests were made by the studio. When the tests proved unappealing, the idea of going from black and white to color during the dream was shelved. For Astaire's golf routine, internal edits were used for the first time in the RKO pictures. Astaire shot the more difficult parts of the routine several times and chose the best take for each one to give the illusion of a perfect performance. Carefree earned RKO $1,731,000 at the box office but ultimately lost the studio $68,000. According to Variety, RKO withdrew Carefree from theatrical circulation in 1980 because of perceived overexposure. Modern sources add Edward Gargan to the cast and credit Mel Berns as make-up artist and John Miehle as still photographer. For more information concerning the Astaire-Rogers RKO films, see entry for Top Hat.