Benny Goodman
Benny Goodman was a jazz clarinetist and band leader famous for the songs "Sing, Sing, Sing" and "One O'Clock Jump." A prodigy on the clarinet, Goodman joined the professional musician's union when he was just 13 years old and made his first recording as a soloist four years later. In the 1920s he played in orchestras, on the radio and for stage shows, and made several recordings as a sideman (including for Bessie Smith and Billie Holiday). In the early 1930s Goodman formed his own orchestra and the Swing Era began. He became a world famous bandleader, appeared regularly on the radio and in the movies and is often credited with introducing jazz to mainstream audiences. By the end of his career he'd had well over 100 hit songs, including "Let's Dance," "Blue Moon, and "Six Appeal."
Extra credit: Benny Goodman is considered the first bandleader to perform in public with a racially integrated orchestra.