Webb, a diminutive hunchback, was universally admired by drummers for his forceful sense of swing, accurate technique, control of dynamics, and imaginative breaks and fills. Although he was unable to read music, he committed to memory the arrangements played by the band and directed performances from a raised platform in the center of the ensemble, giving cues with his drumming.
Using specially constructed bass drum pedals and cymbal holders, he could range effortlessly over a large drum set that offered a wide selection of colors. Unlike drummers of the 1920s, he used the woodblocks and cowbell only for momentary effects, and varied his playing with rim shots, temple-block work, and cymbal crashes. In his celebrated two- to four-bar fills, he abandoned earlier jazz drumming formulae for varied mixtures of duple- and triple- meter patterns. Webb was seldom given to long solos, but his style is well represented on Liza (1938), a superior response to Gene Krupa's solo performance with Benny Goodman's band on Sing, Sing, Sing.