Mighty Shadow

Who is Mighty Shadow?

Winston Anthony Bailey OBE, better known by his stage name The Mighty Shadow or Shadow, is a calypsonian from Trinidad and Tobago. 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 and 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 "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 Humming Bird Medal in 2003.

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".