In 1937 Piney Woods established the all-female jazz orchestra the "International Sweethearts of Rhythm." Most of the members were African American, but the group earned the tag "international" due to the Mexican, Hawaiian and Chinese heritage of some of its members. The group became popular nationally, and in 1941 members decided to break ties with the school in order to get a bigger share of the money they were bringing in. The school replaced them on the road with the Sweethearts' understudies, the Swinging Rays of Rhythm.
Bluesman Sam Myers (1936 - 2006), who was legally blind, attended Piney Woods beginning at age ten. While there he played the trumpet and drums in the school orchestra, toured with the glee club, and learned to play the harmonica by accompanying blues records he bought during visits to Jackson. He also recalled traveling on the road as an assistant to the Swinging Rays of Rhythm.