Born in Pensacola, Florida, Shirley was a promising young student of classical piano. Although he did not achieve recognition in his early career playing traditional classical music, he found success with his blending of various musical traditions.
During the 1960s, Shirley went on a number of concert tours, some in Deep South states. For a year and a half, he hired New York nightclub bouncer Tony "Lip" Vallelonga as his driver and bodyguard. Their story was controversially dramatized in the 2018 film Green Book.
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