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Lady Day: The Many Faces of Billie Holiday tells us the story of one of jazz's greatest singers ever. Although Billie Holiday lived a life filled with tragedy, this documentary focuses more on her achievements as a singer and her exceptional ability to convey emotions through her voice, rather than going into detail about her drug and alcohol addictions and destructive relationships. Lady Day: The Many Faces of Billie Holiday features several brilliant performances of Billie Holiday. Colleagues such as Carmen McRae, Annie Ross, Mal Waldron, Buck Clayton, Harry "Sweets" Edison, and Milt Gabler offer their first-hand perspectives.