On December 4, 1992, Diana Ross took the stage of the Ritz Theatre in New York for a concert commemorating her appearance as Billie Holiday in the film biography Lady Sings the Blues 20 years before. She was backed by an A-list of jazz musicians, and her set list consisted of jazz and pop standards from the 1920s, '30s, and '40s, most of them associated with Holiday. This "special, intimate evening of jazz and blues," as Ross put it, was devoted to "what jazz and blues is really about, which is loose and free and mellow." Despite earning an Academy Award nomination for her acting and topping the pop charts as part of the soundtrack album of Lady Sings the Blues, Ross had not earned much recognition for her jazz singing, and although by 1992 she was four years past the age at which Holiday herself died, she was still essentially a pop singer. Gil Askey's arrangements left plenty of room for the musicians to shine, and the songs were filled with solos by him, Roy Hargrove, Ralph Moore, Urbie Greene, Justin Robinson, musical director Jon Faddis, Jerome Richardson, and Ron Carter. Ross exhibited a bubbly stage presence that played more to the cameras capturing the show than the audio feed, and she sang the songs with warmth and enthusiasm, if without any real resemblance to Holiday or jazz sensibility.
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AllMusic Review by William Ruhlmann