In his teenage years, Isaacs became a veteran of the talent contests that regularly took place in Jamaica. In 1968, he made his recording debut as Winston Sinclair, with the single “Another Heartache”, recorded for producer Byron Lee. The single sold poorly and Isaacs went on to team up with t start the African Museum record label and shop, and soon had a massive hit with “My Only Lover”, credited as the first lovers rock record ever made. He recorded for other producers to finance further African Museum recordings, having a string of hits in the three years that followed, ranging from ballads to roots reggae, including “All I Have Is Love”, “Lonely Soldier”, “Black a Kill Black”, “Extra Classic” and his cover version of Dobby Dobson’s “Loving Pauper”. In 1974, he began working with producer Alvin Ranglin, and that year he had his first Jamaican no. 1 single with “Love Is Overdue”.
Isaacs recorded for many of Jamaica’s top producers during the 1970s, including Winston “Niney” Holness, Gussie Clarke (“My Time”), Lloyd Campbell (“Slavemaster”), Glen Brown (“One One Cocoa Fill Basket”), Harry Mudie, Roy Cousins, Sydney Crooks and Lee “Scratch” Perry (“Mr. Cop”). By the late-1970s, Isaacs was one of the biggest reggae performers in the world, regularly touring the US and the UK, and only challenged by Dennis Brown and Bob Marley. Between 1977 and 1978, Isaacs again teamed up with Alvin Ranglin, recording a string of hits including “Border” and “Number One” for Ranglin’s GG’s label.
He opened the Cash and Carry shop at 118 Orange Street, later moving to no. 125, next door to Prince Buster’s Record Shack, which was also the base for the Cash and Carry record label that he ran with Trevor “Leggo” Douglas.