Over the course of his prolific career — in which he release an estimated 500 albums within Jamaica, the UK and the U.S. — Isaacs collaborated with reggae, dub and dancehall icons like Lee "Scratch" Perry, King Tubby, Sugar Minott, Freddie McGregor, Dennis Brown and Errol Holt. After spending the Seventies building a reputation as both a top-notch roots reggae singer and a soulful "lovers rock"-style crooner, Isaacs recorded his masterpiece Night Nurse at Bob Marley's Tuff Gong Studios in 1982, the year after Marley's death.
Isaacs was poised to become a worldwide star when Night Nurse climbed to Number 32 on the British charts, but instead found himself sentenced to six months in a Jamaican prison on illegal firearm charges. (Isaacs' police record is almost as prolific as his discography, with over 50 reported arrests in his lifetime.) Dubbed the "Cool Ruler" by fans, Isaacs wrestled with drug addiction throughout his career, eventually losing his teeth and jeopardizing his legendary voice from persistent drug use, but he continued to make music, releasing his final album, Brand New Me, in 2008.
Photos: Intimate Moments With Bob Marley During the 'Golden Age of Reggae'