Eckstine possessed one of the most distinctive voices in popular music, a deep tone with a highly personal vibrato. He began singing at the age of 11 but until his late teens was undecided between a career as a singer or football player. He won a sporting scholarship but soon afterwards broke his collarbone and decided that singing was less dangerous. He worked mostly in the north-eastern states in the early 30s and towards the end of the decade joined the Earl 'Fatha' Hines band in Chicago. Although far from being a jazz singer, opting instead for a highly sophisticated form of balladry, Eckstine clearly loved working with jazz musicians and in particular the young experimenters who drifted into the Hines band in the early 40s, among them Wardell Gray, Dizzy Gillespie and Charlie 'Bird' Parker. While with Hines he developed into a competent trumpeter and, later, valve trombonist, having first mimed as a trumpet player in order to circumvent union rules.
In 1943, acting on the advice and encouragement of Budd Johnson, Eckstine formed his own band. Although his original intention was to have a band merely to back his vocals, Eckstine gathered together an exciting group of young bebop musicians and thus found himself leader of what constituted the first true bebop big band. During the band's four-year existence its ranks were graced by Gray, Parker, Gillespie, Gene Ammons, Dexter Gordon, Miles Davis, Kenny Dorham, Fats Navarro and Art Blakey, playing arrangements by Gillespie, Johnson, Tadd Dameron, Gil Fuller and Jerry Valentine. Eckstine also hired the Hines band's other singer, Sarah Vaughan. In 1947 the band folded but had already served as an inspiration to Gillespie, who formed his own bebop big band that year.
Eckstine's commercial recordings during the life of the big band were mostly ballads which he wrapped in his deep, liquid baritone voice, and with his bandleading days behind him he continued his career as a successful solo singer. He gained a huge international reputation as a stylish balladeer. During his long career Eckstine had many hit records, including 'Jelly, Jelly', recorded in 1940 with Hines, 'Skylark', 'Everything I Have Is Yours', 'I Apologize' (stylistically covered by P.J. Proby to great success), 'Prisoner Of Love', 'A Cottage For Sale', 'No One But You' (number three in the UK charts in 1954),'Gigi' (number eight in 1959), and several duets with Vaughan, the best-known being 'Passing Strangers', which, although recorded a dozen years earlier, reached number 17 in the 1969 charts. He went on to record for Motown Records, Stax Records and A&M Records. In later years Eckstine recorded a new single with Ian Levine as part of his Motown revival project on the Motor City label.
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