Billy Eckstine, the handsome, dapper, bandleader and vocalist, turned out popular hits in the 1940s and '50s while playing a pivotal role in the formative years of bebop.
His hit records between 1945 and 1951 included "A Cottage for Sale," "Prisoner of Love," "I Surrender, Dear," "Everything I Have Is Yours," "Blue Moon," "My Foolish Heart," "Caravan," "Body and Soul" and "I Apologize." His last big hit was "Passing Strangers," a duet with the late Sarah Vaughan, whom he helped discover.
Eckstine launched his career in 1934 in a Buffalo, N.Y., nightclub as a singer and emcee.
Five years later, Eckstine went to Chicago as principal vocalist for the Earl (Fatha) Hines big band. With them he wrote and recorded "Jelly Jelly," his first million-selling hit. Such other successes as the blues-oriented ballads "Somehow," "You Don't Know What Love Is" and "Skylark" quickly followed.
Eckstine decided in the spring of 1944 to form his own band, filling it with musicians who would incubate the bop movement: Dizzy Gillespie, Fats Navarro, Miles Davis, Charlie Parker, Dexter Gordon, Kenny Dorham, Art Blakey, Gene Ammons and others.
In 1986, claiming Eckstine owed $251,000 in back taxes, the Internal Revenue Service raided his country club townhouse in Las Vegas and confiscated 110 items of personal property, including three gold records and dozens of musical instruments.
Subsequently, published reports said, an unidentified entertainer and longtime friend purchased the gold records and personal memorabilia from the IRS, saving them from public auction.
Although Eckstine worked in semi-obscurity throughout most of the 1970s, '80s and '90s, he never lacked work. He performed regularly in Miami, California and Las Vegas.