His 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. Began singing at the age of seven and entered many amateur talent shows. Was hired by fellow Pittsburgher Earl "Fatha" Hines to join his Grand Terrace Orchestra in 1939 and by 1943, gained a trio of stellar bandmates—Dizzy Gillespie, Charlie Parker, and Sarah Vaughan. After forming his own big band that year, he hired all three and gradually recruited still more modernist figures and future stars including Dexter Gordon, Miles Davis, Fats Navarro, and another Pittsburgher, Art Blakey. The Billy Eckstine Orchestra was the first bop big-band, and its leader reflected bop innovations by stretching vocal harmonics into normal ballads.
Hit the charts often during the mid-'40s, with Top Ten entries including "A Cottage for Sale" and "Prisoner of Love." Made the transition to string-filled balladry with ease and recorded more than a dozen hits during the late '40s, including "My Foolish Heart" and "I Apologize." Returned to jazz roots, making several albums during the early '60s (one with his son Ed who was the president of Mercury). Appeared on Motown for a few standards albums during the mid-'60s. After recording very sparingly during the '70s, made his last recording, Billy Eckstine Sings with Benny Carter, in 1986. He died of a heart attack in 1993.