If silk sounded like music, it would sound like Billy Eckstine — as smooth as his distinctive voice and look.

The singing veiled a stark reality of challenges faced by African-American singers in his day. Cary Ginell, who wrote about Eckstine’s life in Mr. B: The Music and Life of Billy Eckstine, described it this way: “I consider Billy Eckstine the Jackie Robinson of popular music… Blacks, they would either sing blues or they would be in jazz bands … in vocal groups, like The Mills Brothers … or as a novelty singer. But they were not permitted to enter the domain of Perry Como and Bing Crosby.”

Billy challenged that paradigm. Challenge was part of the Eckstine way, even challenging the concept of bebop with his own band. He was not fond of the term — preferring “progressive jazz” — and demanded respect for the music as a serious studied art form.

The gentle delivery and crooner sensibilities found challenge again when in a 1950 Life magazine profile, a picture showing him being swarmed by admiring white female fans contributed to changing the course of his career. With white radio hosts not playing his recordings on segregated stations, Billy’s words sadly focused the realities: “Maybe Black male singers are not supposed to sing about love… You’re supposed to sing about hurt…”

The artistry includes the all-too-familiar shield — the beauty of the music belying the truer ugliness faced. The artistry was a silkiness so much stronger than hate, a smoothness that rose above and entranced, danced, and excited.