Lewis was born in Kingston, Jamaica. He sang in church from an early age, and started performing as a youth, forming a singing group called the Regals. By the mid-1960s, he began recording and had one of the earliest rocksteady hits with "Take It Easy" in late 1966. The track was recorded with Lynn Taitt and the Jets, and is regarded as one of the first rocksteady singles. He had several more Jamaican hits in the late 1960s and early 1970s, including the first 'herb' song ever recorded there, "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". He began working as a singer with Byron Lee & the Dragonaires, and in 1971 had a hit with "Grooving Out On Life".