Louis Armstrong. Armstrong's influence extends well beyond jazz music, and by the end of his career in the 1960s, he was widely regarded as a profound influence on popular music in general. Armstrong was one of the first truly popular African-American entertainers to "cross over," whose skin-color was secondary to his music in an America that was severely racially divided.
Billie Holiday "Lady in Satin" with Ray Ellis & His Orchestra. One of the great vocal performances captured on record. While this is far from Lady Day at her finest it is a record of vocal art at its peak, an interpretation of pop standards of the day through a life lens. A mythic recording that more than lives up to the lore that surrounds it.