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About Winston Bailey:
Bailey was born in Belmont, a suburb of Port of Spain in Trinidad, but grew up in Les Coteaux, Tobago with his grandparents. He began to sing at a very early age. He wanted to be a singer, although his grandfather told him he must be a lawyer.
He won the Road March in 1974 and 2001 with his songs "Bassman" and "Stranger" respectively. He won the Calypso Monarch in 2000 with "What's Wrong With Me" and "Scratch Meh Back." Bailey is also known for his unique dance moves, where he jumps to the tempo of his music in "skip-rope style" with both feet in the air at the same time. He won the Trinidad & Tobago Humming Bird Medal (Silver) in 2003.
He was the first artist to win both the International Soca Monarch and the Trinidad Road March competitions simultaneously, a feat he accomplished in 2001 with his song "Stranger."