With his distinctive vibrato and highly emotive delivery, Billy Eckstine is widely regarded as the first Black singer to become a star pop vocalist in the big band era. Born in Pittsburgh, PA, in 1914, Eckstine (born Eckstein) toured in bands before moving to Chicago and singing with Earl “Fatha” Hines’ band, sharing the stage with Charlie Parker, Dizzy Gillespie, and Sarah Vaughan. In the ’40s, numerous giants from the next generation of jazz cut their teeth in Eckstine’s bebop ensemble, including Art Blakey and Miles Davis. Over time, however, Eckstine came into his own in the sphere of pop and ballad recordings. His breakout solo hit—the lovelorn ballad “Prisoner of Love” (1945)—was followed up by lushly orchestrated takes on standards like “Everything I Have Is Yours” and “Blue Moon,” which brought his dramatic crooning style into the popular consciousness. “Passing Strangers,” a 1957 reunion with Vaughan, became one of Eckstine’s last charting singles—and a highlight among his prolific discography.