Mizunoe Takiko (1915-2009) and Kasagi Shizuko (1914-1985), born within 6 months of each other in the third year of the Taishō era, both experienced a period of around 2 to 3 years in which they were arguably the most well-known woman in Japan. Despite both being members of the same entertainment organization, the Shochiku Girls Opera Company and occasionally working together, the two women’s careers took quite different trajectories. Today Mizunoe, raised in Tokyo, is generally accepted as the inventor of the otokoyaku (cross-dressing male) role in Japanese musical theater history while Kasagi, from Osaka, is the known for being the first Japanese swing jazz vocalist as well as the woman whose Boogie Woogie songs and comedy roles in movies, “cheered up” Japan in the immediate post-war years. While Kasagi’s life and impact on Japanese popular culture recently received an enormous boost from NHK’s 2023 Asadora (Morning Drama) fictionalizing her life, Mizunoe is today less well known despite an extrordinary career as one of the first female film producers in Japan and the woman who brought Ishihara Shintaro Ishihara’s two pioneering new wave Nikkatsu movies, Taiyō no Kisetsu (Season of the Sun) and Kurutta kajitsu (Crazed Fruit) to a mass audience in the mid-1950s. This slide show presentation examines their careers as part of the presenters’ larger study of the role of women in Japanese pre-and post-war music, film and fashion.