Count Basie and Duke Ellington as by modern jazz pianists, including his cousin Wynton Kelly. The man who impressed him most, however, was the idiosyncratic Thelonious Monk. Weston spent three years learning informally from him, and while he never directly imitated Monk's inimitable approach to the piano, the relationship left a strong mark on Weston's musical sensibilities.
Like Monk, Weston developed his playing and compositional skills in parallel fashion, and he also learned that the piano is not only a melodic and harmonic instrument but also a percussive one. Weston, like Monk, is a very big man, in whose hands the piano keyboard seems veritably to shrink. The title of one of his better-known compositions, "Hi-Fly," apparently reflects his perspective, looking at the ivories down below.
In the late fifties and early sixties Weston led small groups, perhaps the best of which was a sextet that included the great saxophonist Booker Ervin. This combo, like his other ones, mainly played his own compositions and arrangements, some of which, like "Little Niles" and "Hi-Fly," became jazz standards.