Perry's musical career began in the late 1950s as a record seller for Clement Coxsone Dodd's sound system. As his sometimes turbulent relationship with Dodd developed, he found himself performing a variety of important tasks at Dodd's Studio One hit factory, going on to record nearly thirty songs for the label. Disagreements between the pair due to personality and financial conflicts led him to leave the studio and seek new musical outlets. He soon found a new home at Joe Gibbs's Amalgamated Records.