Perry's musical life began in the late 1950s as a record seller for Clement Coxsone Dodd's sound system. As his sometimes bad relationship with Dodd developed, he found himself doing 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 problems, a now normal theme throughout Perry's career, led him to leave the studio and seek new musical outlets. He soon found a new home at Joe Gibbs's Amalgamated Records.