Hibbert was born in May Pen, Parish of Clarendon, Jamaica, the youngest of seven children, he grew up singing gospel music in a church choir. Hibbert moved to Kingston as an teenager in the early 1960s, met Raleigh Gordon and Jerry Matthias, and formed The Maytals. The Maytals became one of the more popular vocal groups in Jamaica in the 1960s, recording with producers Coxsone Dodd, Prince Buster, Byron Lee, Ronnie Nasralla and Leslie Kong. This success included winning Jamaica's National Popular Song Contest three times with songs Hibbert wrote: in 1966 with "Bam Bam", 1969 with "Sweet and Dandy" and 1972 with "Pomps & Pride".