By the mid-1960s, he began recording and had one of the earliest hits with "Take It Easy" in late 1966. He had several more Jamaican hits in the late 1960s and early 1970s, including the first 'herb' song ever recorded in Jamaica, "Cool Collie". He worked for Duke Reid as an arranger and backing vocalist, and won the Festival Song Contest in 1970 with "Boom Shaka Lacka".