William Clarence “Billy” Eckstein (July 8, 1914 – March 8, 1993) was an American singer of ballads 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.
Eckstein's grandparents were William F. Eckstein and Nannie Eckstein, a mixed race, lawfully married couple who lived in Washington D.C.; both were born in the year 1863. William F. was born in Prussia and Nannie in Virginia.
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." 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, but after breaking his collar bone, he made music his focus. After working his way west to Chicago, Eckstine joined Earl Hines' Grand Terrace Orchestra in 1939, staying with the band as vocalist and, occasionally, trumpeter, until 1943. By that time, he had begun to make a name for himself through the Hines band's radio shows with such juke box hits as "Stormy Monday Blues" and his own "Jelly Jelly."