Wilson was born in Austin, Texas, on November 24, 1912. He studied piano and violin at Tuskegee Institute in Tuskegee, Alabama. After working in Speed Webb’s band, with Louis Armstrong, and also understudying Earl Hines in Hines’s Grand Terrace Cafe Orchestra, Wilson joined Benny Carter’s Chocolate Dandies in 1933. In 1935, he joined the Benny Goodman Trio (which consisted of Goodman, Wilson and drummer Gene Krupa, later expanded to the Benny Goodman Quartet with the addition of Lionel Hampton). The trio performed during the big band’s intermissions. By joining the trio, Wilson became one of the first black musicians to perform prominently in a racially integrated group.
Wilson formed his own short-lived big band in 1939, then led a sextet at Café Society from 1940 to 1944. He was dubbed the “Marxist Mozart” by Howard “Stretch” Johnson due to his support for left-wing causes: he performed in benefit concerts for The New Masses journal and for Russian War Relief, and he chaired the Artists’ Committee to elect Benjamin J. Davis. In the 1950s, Wilson taught at the Juilliard School. Wilson can be seen appearing as himself in the 1955 motion picture The Benny Goodman Story. He also worked as music director for the Dick Cavett Show.