Given his early musical partnership with Billie Holiday at a time when America was still segregated, Shaw clearly had a taste for risk. That's borne out in his slyly experimental sound. What other white clarinetist could take a Mexican song, have it arranged by African-American composer William Grant Still, and then ride it to the top of the pop chart? (That's just what Shaw did in 1940 with the future standard "Frenesi.") Toying skillfully with mainstream expectations, his adventurism rings clear both in small combos and within big ensembles featuring silky string sections.