Popular Trinidadian Calypsonian Winston “The Mighty Shadow” Bailey passed away this morning at the age of 77.
Shadow suffered a stroke on Sunday and died this morning at the Mt Hope Hospital at 3:40am.
Bailey was expected to be conferred with an Honorary Doctor of Literature degree from the University of the West Indies this weekend for his contributions as a musical composer.
Bailey was born in Belmont, a suburb of Port of Spain in Trinidad, but grew up in Les Coteaux, Tobago, with his grandparents.
He won the Road March in 1974 with “Bassman” (where he also placed second with “I Come Out to Play”) and in 2001 with “Stranger”, making him the competition’s oldest winner. 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.
Shadow’s influence on the art form is tremendous. His influence can be heard throughout the years even today in popular songs and road marches.
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 “Stranger”.