When Miles Davis got his first chance to play with Diz and Bird in St. Louis in 1944, he had the fortune of playing third trumpet in Billy Eckstine's Orchestra.
A win in a talent contest prompted Eckstine's drop from Howard University and early career as a jazz singer. His first big break came in 1939 when he joined Earl Hines's big band as vocalist and occasional trumpeter. He sang for Hines and his name grew in popularity with the band's radio performances. Eckstine (or Mr. B) would leave Hines to form his own big band in 1943 taking many of Hines's young musicians with him including Dizzy Gillespie, Dexter Gordon, Art Blakey, and Charlie Parker. With Gillespie's early arrangements, Billy Eckstine and His Orchestra became the first bop big band, a risk for all involved due to bebop's critical and commercial unpopularity at the time. Despite the prejudice against this groundbreaking new jazz, Eckstine's voice carried the Orchestra's singles (like "A Cottage for Sale" and "Prisoner of Love") to be Top Ten hits and helped set the stage for bebop dominance in jazz for the next decade.
Here is the discography surrounding Billy Eckstine's first two years of recording:
A Cottage for Sale (1945 single with His Orchestra)
I'm in the Mood for Love (1945 single with His Orchestra)
Prisoner of Love (1945 single with His Orchestra)
The Chronological Classics: Billy Eckstine and His Orchestra 1944-1945
"I Love the Rhythm in a Riff" by Billy Eckstine and His Orchestra
"Prisoner of Love" by Billy Eckstine and His Orchestra
Pass the Headphones!!
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