[1] He attended music school, and his teacher Chuck Bird arranged for him to perform with the Jackie Gleason Orchestra in front of Spiro Agnew in 1965.
He was also a member of The Sheridans (with Pat Kelly) In the late 1960s he recorded as a solo artist for Clement "Coxsone" Dodd's Studio One label, with his debut album Mr. Fix-It released in 1969.
[1] From 1968 to 1972 Winston had numerous 7" releases on labels such as JJ's, Supreme, WIRL, Bamboo, Coxsone, Punch, Studio One, Tiger, Banana, Decca, Rhino.
[1] He continued to record in the 1990s, working with Dennis Bovell under the name King Cool, and releasing Ragga Love and Sweet Rock Steady, and guested on Kelly's 1995 album Butterflies.
[2] His version of Ben E King's "Stand by Me" was a hit in France, selling over 90,000 copies, leading to work with Sly & Robbie and John Kpiaye.