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Mighty Shadow

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The Might Shadow (Winston Bailey) was born in Belmont, a suburb of Port of Spain, Trinidad in 1941. However, he spent his childhood years in Les Coteaux, Tobago.

He won the Road March in 1974 and 2001 with "Bassman" and "Stranger" respectively. He won the Calypso Monarch in 2000 with "What's Wrong With Me" and "Scratch Meh Back." Shadow is also known for for his unique dance in which he jumped 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.