At the age of 18, he sang tenor one night at the Memorial Auditorium in Spartanburg, SC with the Pine Ridge Boys. Some years later, he returned to that group to sing lead. After singing with the Pine Ridge Boys, he joined the Tar Heel State Quartet and sang with them for a while before joining Ed Crawford and the Mystery Men to sing bass. When Charlie Waller formed a new version of the Florida Boys, Chip initially was their bass singer. Later he transitioned to the baritone position.
His short tenor career and his extended stints at lead, baritone and bass combine to make Chip Cooper one of only a few individuals who have sung all four quartet parts at various stages of their careers.