McGregor was born in Clarendon, Jamaica on June 27, 1956. At age seven, he started singing backup for a local ska harmony duo called the Clarendonians.
He sang lead for groups like Generation Gap and Soul Syndicate, and also recorded off and on as a solo act during the ’70s. In 1975, McGregor converted to Rastafarianism. In 1981, McGregor scored a huge hit single with “Big Ship,” which catapulted him to the front rank of reggae stars in the immediate post-Marley era, along with Dennis Brown and Gregory Isa.