This documentary follows six pioneering female jazz singers – Billie Holiday, Ella Fitzgerald, Peggy Lee, Sarah Vaughan, Nina Simone, and Annie Ross – as they navigate the challenging music scene of mid-20th century America. The film explores their journeys from the rough-and-tumble world of big bands in the 1930s and 40s to becoming influential figures in nightclubs and saloons throughout the 1950s and early 1960s. Through interviews with those who knew and worked with these jazz legends, and with contemporary singers who have been inspired by them, the film highlights the struggles they overcame to establish themselves as unique artists in a prejudiced era.