KingIssachar son of Mr and Mrs Winston Pennycook. KingIssachar grew up in Westmoreland Jamaica and from an early age was performing in the church. The earliest breakthrough came by KingIssachar performing in the Colgate Cavity Fighter's Club in Jamaica where he recited a poem called "Apple Trees". KingIssachar then went on to start dee-jaying on sound systems that visited the parish of Westmoreland. His love of music gave him the opportunity to dee-jay on Count Palmer's Sound System which was one of Westmoreland's sound at the time. He then went on to dee-jay on his brother's nephew's sound system called "Turbo Phonic", in which at the time, was one of Westmoreland's leading sound systems.