Reggae's "Cool Ruler" earned his nickname for his unforgettably smooth vocals -- which he's given listeners plenty of chances to hear. Since debuting in the late 1960s as a member of harmony group the Concordes, Isaacs has released some 500 singles and well over 70 albums; a feat made more remarkable because of on-again, off-again drug problems and skirmishes with the law.

Though the Kingston native quickly won a reputation as a ladies' man, thanks to hits like "All I Have Is Love," his songs also dealt frequently with the realities of ghetto life -- the early single "Loving Pauper" being a notable example that combined both themes. That hit and others, like "Cool You," made Isaacs one of the most popular stars in Jamaican music during the 1970s; teaming with red-hot session men Sly and Robbie and the Roots Radics further boosted his profile as the decade changed. "Night Nurse," from 1983, remains perhaps his best-known album and is sometimes credited with kick-starting the lovers rock genre, but gun and drug charges -- and a subsequent Jamaican penitentiary stint -- derailed his career in the mid-80s. Undeterred, Isaacs made a huge comeback with 1988's "Rumours," a dancehall smash that reunited him with producer Gussie Clarke.

Though time and the high life have combined to rob his voice of some of its breathtaking qualities, Isaacs continued to regularly add to his massive catalog during the 1990s. When teamed with the right producer, the results can still be magical, as 1993's Absent and 1996's Private Lesson prove.