Diana Ross and Billy Dee Williams meet in LADY SINGS THE BLUES ('72). The film was nominated for five Academy Awards including Best Actress for Ross' portrayal of legendary singer Billie Holiday | Turner Classic Movies: TCM

Loosely based on jazz legend Billie Holiday’s memoir, LADY SINGS THE BLUES ('72) had a formidable cast, including Billy Dee Williams, Richard Pryor, and former member of "The Supremes," Diana Ross. Critics were initially skeptical of Ross's lack of acting experience and her singing style which differed from Holiday's, but were proven wrong by her impressive performance. For her film debut, Ross received her first Oscar nomination. See it tonight at 11:45pm ET. | Turner Classic Movies: TCM