By the time Bing Crosby and Fred Astaire made Holiday Inn (1942), they were already stars of the first magnitude. Crosby had been in films since 1930 and was the top-ranked player at Paramount. Astaire had been in films since 1933. Prior to their film careers, they both had extensive experience in other media: vaudeville, recordings, radio, concerts, and musical theater. When recruited by Hollywood, Astaire was a star of the Broadway and London stage. By 1942, all but one of his movies with Ginger Rogers had been completed. Crosby had already appeared in numerous important films in which he sang and acted, including two of the “Road” pictures, The Road to Singapore (1940) and The Road to Zanzibar (1941). The Road to Morocco (1942) would be released the same year as Holiday Inn. Total triumph was still to come with Going My Way (1944) and The Bells of St. Mary's (1945).

By the time Blue Skies (1946) was released, canonization had been bestowed on Crosby. Both stars were, in fact, so successful and so sought after that they commanded substantial salaries, which accounts for the two relatively unknown female leads in Holiday Inn. The studio could not have afforded equivalent price tags for the stars’ love interests played by Virginia Dale and Marjorie Reynolds. Because Holiday Inn was such an enormous hit, Paramount pulled out all the stops with Blue Skies: Technicolor, lavish sets and costumes, production numbers and considerably more backup in terms of supporting cast. Olga San Juan is a case in point; she adds a decent dash of sex appeal in her singing, dancing, and acting assignments. She performs with what one critic calls “sassy suggestiveness.” San Juan provides a particularly effective addition since her spicy performance contrasts sharply with the vapid one given by the leading lady, Joan Caulfield.