Born Elinore Harris, Billie Holiday had a difficult teen and young adulthood period, which included working in brothels, both as a cleaning woman and a prostitute, and being raped. Through this difficulty, she dreamed of becoming a jazz singer. She got her initial singing break when she applied at a Harlem club that was looking for a dancer, but where she got hired as a singer. There, she met and fell in love with the suave Louis McKay.
Diana Ross plays the magnificent, tragic song stylist Billie Holiday, who while writhing in a strait jacket in a prison cell, awaiting sentencing on drug charges, reflects on her turbulent life. Raped in her youth by a drunk (Adolph Caesar), then compelled to work as a domestic in a Harlem whorehouse, Holliday is encouraged to try for a singing career by the bordello's pianist (Richard Pryor). She rises as high as it is possible to go in the white-dominated show business world of the 1930s, but can't handle the pressure and turns to narcotics. The film takes several liberties with the 44-year existence of "Lady Day." Among the Billie Holiday standards performed by Ross are "My Man," "I Cried for You," "Lover Man," "Them There Eyes," and the title song.
When Sony/Columbia began its ambitious Legacy reissue project, those who followed their jazz titles knew it was only a question of time before the massive Billie Holiday catalog under their ownership would see the light in its entirety. The question was how? Years before there was a host of box sets devoted to her material, but the sound on those left something to be desired. Would they remaster the material in two- or three-disc sets with additional notes? Would it be one disc at a time? Would the material be issued as budget or midline material or at full price? The last item could be ruled out based on the label's aggressive and very thorough packages of single discs by Charles Mingus, Miles Davis, Duke Ellington, and others.
Lady Sings the Blues expands the template of jazz-driven torch songs to embrace soul and '60s pop as well, thus its success at presenting a compilation with depth and variety.