His airy, effortless style, with its emphasis on lightly accompanied right-hand melody, was a key element in the transition from swing to bebop, and many modern jazz pianists took Wilson's approach as their starting point. His early recordings were percussive and forceful, but as he matured his technique became graceful, almost elegant. He was a gifted artist who used the full range of his instrument to his advantage. His recordings with Billie Holiday and Benny Goodman’s trio and quartet during the 1930s are considered classics.
Wilson was born in Austin, TX in 1912, his parents were both schoolteachers. They left Texas in 1918 for positions at the prestigious Tuskegee College in Talladega, AL, one of the pioneer black universities. Wilson studied music at both the Tuskegee Institute and Alabama's Talladega College.
Moving on to Detroit and Toledo, Ohio, he started by joining up with Speed Webb and Milton Senior before heading to Chicago, where he played with the likes of Erskine Tate, Eddie Mallory, Clarence Moore, Jimmy Noone and Louis Armstrong. He traveled to New York in 1933 to join Benny Carter's orchestra, the Chocolate Dandies. After Carter disbanded the following year to take a position as arranger with Goodman's band Wilson worked with an all-star group led by Red Norvo in 1934 and with Willie Bryant's band during 1934 and 1935. He met Goodman in 1935 and in 1936 was asked to join the bandleader's trio, which also included drummer Gene Krupa. Lionel Hampton joined soon after, making it a quartet. Wilson became the first African-American publicly featured in Goodman's line-up.