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Born in Kingston, Stewart was half of the duo Winston and Bibby, along with B.B. Seaton. The two formed the Gaylads along with Maurice Roberts in the late 1950s. Stewart left the group in the late 1960s, having already recorded a handful of solo singles, and recorded as a solo artist for producer Sonia Pottinger. In 1969 he relocated to the United States.
An album of his recordings for Pottinger was released in 1970. A compilation of his solo work up to 1973 was released in 2001.