Freddie McGregor

Freddie McGregor is one of reggae’s most durable and soulful singers, with an incredibly steady career that started all the way back in the ’60s, when he was just seven years old. Since then, he’s spanned nearly every stylistic shift in Jamaican music, from ska and rocksteady to Rastafarian roots reggae to lovers rock (his particular specialty) to dabblings in dancehall, ragga, and dub. Not just a singer, he wrote some of his own material, and grew into an accomplished producer as well. McGregor’s heyday was the early ’80s, when he released several high-quality albums and reached the peak of his popularity in Jamaica and England. However, he remained a strong presence on the reggae scene well into the new millennium. 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 (naturally, with the nickname of Little Freddie McGregor). the Clarendonians recorded for producer Clement “Coxsone” Dodd’s legendary Studio One label for a time, and when they split in the mid-’60s, McGregor teamed up with ex-member Ernest “Fitzroy” Wilson to form a new duo, Freddie and Fitzroy. They recorded several single sides, including “Why Did You Do It” and “Do Good and Good Will Follow You.” McGregor stayed at Studio One for much of the ’70s, working as a session drummer and backup singer while developing his own vocal style, which owed much to smooth, Philadelphia-style soul. He sang lead for groups like Generation Gap and Soul Syndicate, and also recorded off and on as a solo act during the ’70s, though always in the singles medium. During this period, he began writing some of his own material, including songs like “Go Away Pretty Woman,” “Tomorrow Is Like Today,” and “What Difference Does It Make.”