Known as "The Cool Ruler" for his smooth, passionate voice and laidback style, 5 time Grammy Award nominated, Gregory Isaacs was first spotted at a talent show which led to him recording a duet with Winston Sinclair in 1968 and later forming part of the vocal trio "The Concords". He was inspired by stars such as Sam Cooke, Otis Redding and Alton Ellis, but named his mother as his first vocal role model, since he used to hear her singing while she ironed.

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Although the singles released with these groups did not catch the attention of the public to the scale they would have hoped, this only drove Gregory. In 1973, he set up his record store and label in collaboration with Errol Dunkley. The label was called "African Museum", and one of its first releases was Isaac’s self-produced “My only lover”. It was an immediate hit, one of many to come. 

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It's estimated that Gregory Isaacs has released over 500 records in his career, which includes singles and compilations.

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Alongside his music career, Gregory made an appearance in the 1978 feature film Rockers.

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Gregory Isaacs died of lung cancer age 59 on 25 October 2010, but his legacy continues through The Gregory Isaacs Foundation and in 2016 the Jamaican government awarded Gregory Isaacs the Order of Distinction (Officer Class) to recognise his contribution to the country’s music.