Eckstine, who also played valve trombone, became a major attraction with the Hines orchestra with his exquisite vocal renderings of ballads and intense performances of blues numbers like this, his best known tune with the band: "Jelly, Jelly" (1940) The performance is robust and bluesy, but also smooth and even elegant.
A number of younger Hines sidemen were deep into the new bebop movement, among them Charlie Parker, Dizzy Gillespie, Budd Johnson, Tommy Potter, Miles Davis, Fats Navarro, J.J. Johnson, Frank Wess, Gene Ammons, Dexter Gordon, Sonny Stitt, Leo Parker and another fellow Pittsburgher Art Blakey (seen in the Eckstine Orchestra clips below). Eckstine, too, loved the sound and left Hines in 1943 to lead his own group.
Billy Eckstine and his Orchestra became the first big band to fully embrace bebop, the leader's smooth vocalizing giving them a commercial sheen that allowed them to survive for four years. This is "Rhythm in A Riff," a demonstration of the bop band at their best and most blazing.
He capably handles vocals on the pop standard "Prisoner of Love" and "Lonesome Lover Blues."
Eckstine dissolved the band to go solo in 1947. From then on his rich baritone was the focus. It lent itself to romantic ballads, Like Nat King Cole, his s appeal transcended race. These were two of his biggest pop hits: his 1949 rendering of "Blue Moon" (the same song The Marcels later made famous with a dramatically different treatment).
And "My Foolish Heart," a hit single in 1950.
Eckstine was also a fashion trend-setter, as his rolled-collar dress shirts became popular as "Mr. B" style shirts among hip dressers in the late 40's.
This rendition of the timeless ballad "September Song" from a TV performance is Eckstine at his peak.
Eckstine's records, like those of Nat Cole, who'd gained his first notice as a titan of jazz piano, downplayed his jazz roots to attract wider appeal, but he never abandoned jazz. Case in point: when Cole briefly hosted a 1950's NBC variety show, he had freedom to select guests and present jazz and return to the keyboard. Eckstine joined him on one show, where they perform Earl Hines's "Rosetta," allowing them to demonstrate still-formidable jazz chops. Not sure what that last instrument is Billy's playing, but it sure sounds more like a trombone than a sax.
In the 1960's or early 70's, Eckstine made another TV appearance, this one probably from the "Playboy After Dark" TV series. Sadly, his perfunctory attempt to sound relevant doing contemporary material clearly unsuited to his style, don't work well. This is the sort of thing Columbia Records wanted Tony Bennett to do during this same time. Tony refused.
Eckstine's later musical career wasn't nearly as fulfilling, as he found himself recording for Motown. Too often, singing songs like the above that simply didnt fit his timeless style. He never found the redemption of a Bennett, who enjoyed a career revival that made him a favorite with multiple generations. Eckstine deserved a better finish.
Jazz critic Will Friedwald said as much in his book A Biographical Guide to the Great Jazz and Pop Singers, "In performance, Eckstine was still remarkable, but unfortunately his final recordings seem to capture all the shortcomings and little of his elder statesman majesty."
PS. That State historical marker for Eckstine was placed in part due to the efforts of the late and sorely lamented WDUQ.
Eckstine, who'd suffered a stroke that ended his performing career, was 78 when he died in Pittsburgh in 1993.