By the time he reached his peak popularity in 1950, he rivaled Frank Sinatra as the country's most popular vocalist. In fact he was dubbed the sepia Sinatra, although he was known most often as Mr. B. Billy Eckstine was a smooth singer also noted as a premier jazz bandleader in the 1940s, gathering many of the performers in the innovative bebop style into a unique large band.
Born William Clarence Eckstein in Pittsburgh, Pennsylvania, in 1914, Eckstine had the spelling of his name changed early in his career by a club owner. The family moved to Washington, D.C. Eckstine's parents stressed education, and he graduated from Washington's Armstrong High School. He began to sing when he was 11, but was a football player in high school and aspired to a sports career for a time. Eckstine went on to college at the city's Howard University. A first-place finish in a talent contest at a Washington theater put an end to his educational career, however; he dropped out of school to sing full time.
At first Eckstine appeared in and around Washington, D.C., but had moved to Chicago by 1937. Pianist and bandleader Earl Hines hired him as his lead vocalist for his Grand terrace Orchestra in 1939. During a four-year stint with Hines, Eckstine broadened his vocal skills, learned to play the trumpet, and met many of the jazz players who were experimenting with new styles. All this made for ideal training as Eckstine dreamed of starting a band of his own. He notched several hits with Hines, the first of which was the bluesy Jelly, Jelly of 1940. When he introduced the song Skylark on a network radio program, he was the first African American vocalist to premiere a mainstream pop song on the radio.