Gregory Isaacs, the Jamaican-born reggae singer who began recording in his teens and released more than 500 albums over the course of a 40-plus-year career, has died after a battle of lung cancer. He was 59. Isaacs earned the nickname “Cool Ruler” for his smooth singing voice, a silky baritone that he used to great effect on landmark records like “My Only Lover” in the “lovers rock” subgenre of reggae, which traded the political messages of Rastafarian reggae for a breezier, more seductive sound. Isaacs had most of his biggest hits in the 1970s, although he is likely best known internationally for his part playing “Slavemaster” in the 1978 film Rockers, or his 1982 club favorite “Night Nurse,” which was later remade into a hit for Simply Red. Isaacs spent most of his career in and out of jail for cocaine possession, a habit that also stripped away his voice, but he kept on touring and recording right up until his death. His last album was 2008’s Brand New Me.

He was also a super snazzy dresser.