	Born in Miami, Florida, Jackson joined Duke Ellington alumnus Cootie Williams's band in 1949 as a teenager, after being discovered by Eddie Vinson. During the 1950s Jackson participated in R&B and jazz recordings, primarily as a session musician. He also toured as leader of the backing band of singer Ruth Brown whom he married . In the biography of Ruth Brown however is no mentioning of Willes Jackson. There it is mentioned that she was marries to trumpeter Jimmy Brown. Jackson joined Prestige Records in 1959, making a string of jazz albums that proved to an influence on the burgeoning soul jazz movement. During this era, Jack McDuff and Pat Martino became famous through association with Jackson. Jackson's main influences were Lester Young and Illinois Jacquet.