In 1900–01, Cooper joined Richards and Pringles Georgia Minstrels. Unlike the other minstrel performers in the group, Cooper performed as a ventriloquist and did not wear blackface as part of their act. The minstrels, an act that got its start in the 1830s before vaudeville and burlesque, typically participated in an overtly racist style of performance known as blackfacing in which the singers and dancers would paint their faces with black cosmetics that mocked African Americans. Cooper essentially performed in minstrel shows but was not a minstrel himself and introduced a performance style that contrasted blackfacing. After touring with Richards and Pringles Georgia Minstrels, he became known as “the Black Napoleon of ventriloquism.” He then joined Rusco and Holland's Big Minstrel Festival at the end of 1901.