William Clarence ?Billy? Eckstine 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.
Eckstine's grandparents were William F. Eckstine and Nannie Eckstine, 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. His parents were William Eckstein, a chauffeur and Charlotte Eckstein. Billy attended Armstrong High School, St. Paul Normal and Industrial School, and Howard University. He left Howard in 1933, after winning first place in an amateur talent contest. He married his first wife, June, in 1942; she too was a vocalist. After their divorce he married Carolle Drake in 1953; they were divorced in 1977. He was the father of 7 children, including Ed Eckstine who was a president of Mercury Records, Guy Eckstine who was a Columbia Records executive, and singer Gina Eckstine.
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."
In 1944, Eckstine formed his own big band and made it a fountainhead for young musicians who would reshape jazz by the end of the decade, including Dizzy Gillespie, Dexter Gordon, Miles Davis, Art Blakey, Charlie Parker, and Fats Navarro. Tadd Dameron and Gil Fuller were among the band's arrangers, and Sarah Vaughan gave the vocals a contemporary air. The Billy Eckstine Orchestra was the first bop big-band, and its leader reflected bop innovations by stretching his vocal harmonics into his normal ballads. Despite the group's modernist slant, Eckstine hit the charts often during the mid-'40s, with Top Ten entries including "A Cottage for Sale" and "Prisoner of Love". On the group's frequent European and American tours, Eckstine, popularly known as Mr. B, also played trumpet, valve trombone and guitar.