The Piney Woods School was founded by
Laurence C. Jones and the first classes were held outside in 1909. Similar to earlier ventures by blacks, the school had financial difficulties and the Cotton Blossom Singers was formed to raise money for the building. Jones's wife,
Grace Morris Allen Jones, led the first iteration of the group although it is disputed what year they first sang. Historian Beth Day thinks that this first happened in spring 1921, but historian Alferdteen Harrison has suggested that the first group sang in summer 1923. Grace's role was sometimes to be the pianist, but she did not think of herself as a musician. The first group of the Cotton Blossom Singers sang spirituals and folk songs. In 1926, four groups of students toured through the United States; later, up to 13 groups toured at the same time, each group assigned to their own region. The name Cotton Blossom Singers was only used when the groups were touring, and they were called The Piney Woods Singers in their hometown. Some interviewees thought that Laurence C. Jones used the national tour name so that whites in the northern and eastern United States would be interested. Some of those whites became confused due to the Cotton Blossom Singers not being a
minstrel show. Each group had issues booking hotels during the 1920s due to their race. They attached their luggage to cars, while usually eating food that had to be kept cold and sometimes eating food cooked outside over a fire. The founder of the company
Mentholatum, Albert Alexander Hyde, gave the Cotton Blossom Singers a car containing essentials such as bunk beds and cooking tools with a similar car being built soon after. The groups toured the United States for up to 16 months. ==Musical content==