Winston Anthony Bailey, better known as The Mighty Shadow or Shadow, is a true legend and backbone of Trinidad and Tobago.
No other singer in the calypso arena is more mysterious, mesmerizing or controversial.
Bailey was born in Belmont, Port of Spain, but grew up in Les Coteaux, Tobago, with his grandparents Evlan and Elly Bailey until he was 14.
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 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 Hummingbird Medal (Silver) in 2003.
Shadow also won awards from NJAC, a small political party with strong cultural interests. His songs normally make the Top 20 calypso list every year. He hangs the awards over his door. His 1994 album Dingolay won a Caribbean Music Award for the best-engineered album.
He was the second to win both the International Soca Monarch and the Trinidad Road March competitions simultaneously, a feat he accomplished in 2001 with his song “Stranger”. Shadow revolutionized calypso with a restless spirit that guides him more than he guides the music.