Billy 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 Grand Terrace Orchestra in 1939. Though white bands of the era featured males singing straightahead romantic ballads, black bands were forced to stick to novelty or blues vocal numbers until the advent of Eckstine and Herb Jeffries (from Duke Ellington's Orchestra).

Though several of Eckstine's first hits with Hines were novelties like "Jelly, Jelly" and "The Jitney Man," he also recorded several straightahead songs, including the hit "Stormy Monday." By 1943, he 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: Wardell Gray, Dexter Gordon, Miles Davis, Kenny Dorham, Fats Navarro, and Art Blakey as well as arrangers Tadd Dameron and Gil Fuller. 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 also played trumpet, valve trombone and guitar.

Though he was forced to give up the band in 1947 (Gillespie formed his own bop big-band that same year), Eckstine made the transition to string-filled balladry with ease. He recorded more than a dozen hits during the late '40s, including "My Foolish Heart" and "I Apologize." He was also quite popular in Britain, hitting the Top Ten there twice during the '50s -- "No One But You" and "Gigi" -- as well as several duet entries with Sarah Vaughan. Eckstine returned to his jazz roots occasionally as well, recording with Vaughan, Count Basie, and Quincy Jones for separate LPs, and the 1960 live LP No Cover, No Minimum featured him taking a few trumpet solos as well. He recorded several albums for Mercury and Roulette during the early '60s (his son Ed was the president of Mercury), and he appeared on Motown for a few standards albums during the mid-'60s. After recording very sparingly during the '70s, Eckstine made his last recording (Billy Eckstine Sings with Benny Carter) in 1986. He died of a heart attack in 1993.

By Elizabeth Wellington Billie Holiday is beaming in a 1956 photograph as she gazes at singer Billy Eckstine. Her trademark flower is pinned behind her left ...

She recorded a fine debut LP in 1961 and apprenticed through the '60s and early '70s with Cal Tjader, Dizzy Gillespie, Billy Eckstine and Count Basie. ...

His style is butter-smooth, a descendant of the noble line of singers that proceeded from Billy Eckstine through Johnny Hartman and Kevin Mahogany -- and ...

Perhaps the most lovely (and least known) subject though in Hadju's book is Billy Eckstine, a black jazz singer who equaled Frank Sinatra's star power in ...