From the 1940s, Billy Eckstine’s smooth baritone and distinctive vibrato broke down barriers, initially as the leader of the original bop big band, then as the first romantic black male in popular music.
The singer and bandleader achieved great personal success, but also fostered the careers of a number of younger jazz musicians. Eckstine’s pop hits “Prisoner of Love,” “My Foolish Heart” and “I Apologize” made him a fan favorite.
The Pittsburgh native raised in Washington, D.C., began singing early and hoped to have a career in football but a broken collar killed that dream. During the late ’30s, Eckstine who had come to Chicago got hired by Earl Hines to join his Grand Terrace Orchestra in 1939. His first hits with Hines were novelties like “Jelly, Jelly” and “The Jitney Man,” but he also recorded several straight-ahead songs, including the hit “Stormy Monday.”
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From 1939 to 1943 Eckstine sang with Hines’s band, and at his urging Hines hired such newcomers as Sarah Vaughan, Dizzy Gillespie, and Charlie Parker. In 1944 Eckstine formed his own band, which in its three-year existence gave strong impetus to the new bebop style by featuring the talents of Miles Davis, Fats Navarro, Gene Ammons, Dexter Gordon, Tadd Dameron, Art Blakey, Dizzy Gillespie, Charlie Parker as well as arrangers Tadd Dameron and Gil Fuller.
The Billy Eckstine Orchestra was the first bop big-band group and its leader reflected bop innovations (early form of modern jazz originating around 1940) 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.
Eckstine’s sex appeal and suave singing made him one of the earliest black stars to be loved by white female fans, despite the strong racial tensions of the 1950s.
He was the subject of a three-page profile in the 25 April 1950 issue of LIFE magazine. One photograph taken by Martha Holmes and published in LIFE showed Eckstine with a group of white female admirers, one of whom had her hand on his shoulder and her head on his chest while she laughed.
The photo was first described as “harmony” or “breaking racial barriers.” The publication of the image caused letters of protest to be written to the magazine, and singer Harry Belafonte subsequently said of the publication that “When that photo hit, in this national publication, it was if a barrier had been broken”. The controversy that resulted from the photograph had a seminal effect on the trajectory of Eckstine’s career.
Tony Bennett would recall that, “it changed everything… Before that, he had a tremendous following…and it just offended the white community”, a sentiment shared by pianist Billy Taylor who said that the “coverage and that picture just slammed the door shut for him.”
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.
Eckstine suffered a stroke while performing in Salina, Kansas, in April 1992, and never performed again. Though his speech improved in the hospital, Eckstine had a heart attack, and died a few months later on March 8, 1993, aged 78.