Charles Phillips Thompson, was born on 12 March 1918, in Springfield, Ohio. After starting out on violin Thompson switched to piano and was playing professionally by his mid-teenage years. During the mid- to late 30s he played with several notable territory bands in the south-west, including that led by Nat Towles. In 1940 he was briefly with Lionel Hampton's big band but preferred small group work, although he regularly wrote arrangements for musicians including Count Basie and Jimmy Dorsey.
During the 40s and 50s Thompson worked with leading jazzmen such as Lester Young (who bestowed upon him the title by which he was subsequently known), Coleman Hawkins, Illinois Jacquet, Jimmy Rushing and Buck Clayton, the last an especially important musical associate.