His music told us stories about ourselves through poignant social commentary which was often fused with wry humour. Over the years his contribution to the development of our local music earned him regional and international acclaim.
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For his distinguished contribution to calypso music Winston Bailey, the Shadow, was awarded the prestigious Hummingbird Silver Medal in 2003. The “Bassman”, as he is also known to the musical world won the Road March title in 1974 with “Bassman” and in 2001 with “Stranger”.
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He also won the Calypso Monarch in 2000 with “What’s Wrong with Me” and “Scratch Meh Back”. For many his rendition of "I Believe" will always define the class and talent of this superb performer and social commentator.
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We are honoured to have witnessed the life of this great musician and to have experienced his outpourings of the best of our calypso culture. We are grateful for the music he gave us and proud of his legacy which will remain undiminished for all time.
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