Trinidadian calypsonian, Mighty Shadow, Died at 77


Winston McGarland Bailey HBM DLitt was born on October 4, 1941, in Belmont and died on October 23, 2018.

He better was known by his stage name The Mighty Shadow or Shadow,

He was a calypsonian from Trinidad and Tobago.

Bailey was born a suburb of Port of Spain in Trinidad but grew up in Les Coteaux, Tobago, with his grandparents.

Mighty Shadow started to sing at a very early age and he wanted to be a singer.

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”.

He was 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.

The Mighty Shadow was an influence on the art form is tremendous.

Shadow was the second person to win both the International Soca Monarch and the Trinidad Road March competitions simultaneously, a feat he accomplished in 2001 with “Stranger”.

Winston McGarland Bailey passed away at 77 years old.


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