Bolton is best known for his early work on the Princess Theatre musicals during the First World War with Wodehouse and the composer Jerome Kern. These shows moved the American musical away from the traditions of European operetta to small scale, intimate productions with what the "Oxford Encyclopedia of Popular Music" calls "smart and witty integrated books and lyrics, considered to be a watershed in the evolution of the American musical." Among his 50 plays and musicals, most of which were considered "frothy confections", additional hits included "Primrose" (1924), the Gershwins' "Lady, Be Good" (1925) and especially Cole Porter's "Anything Goes" (1934).