Billy Eckstine (8 July,1914–8 March, 1993), born William Clarence Eckstein in the East Liberty neighborhood of Pittsburgh, Pennsylvania, was a ballad singer and bandleader of the Swing Era. Eckstine's smooth baritone and distinctive vibrato broke down barriers throughout the 1940s, first as leader of the original bop big-band, then as the first romantic black male in popular music. An influence looming large in the cultural development of soul and R&B singers from Sam Cooke to Prince, Eckstine was able to play it straight on his pop hits "Prisoner of Love," "My Foolish Heart" and "I Apologize." Born in Pittsburgh but raised in Washington, D.C., Eckstine began singing at the age of seven and entered many amateur talent shows. He had also planned on a football career, though after breaking his collar bone he made music his focus. After working his way west to Chicago during the late '30s, Eckstine was hired by Earl Hines to join his Gran

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