Mighty Shadow

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The Mighty Shadow
Born (1941-10-04) October 4, 1941 (age 77)
Origin Belmont, Trinidad and Tobago
Genres Calypso, Soca
Occupation(s) Musician, Singer, producer, Song-writer
Instruments Vocals

Winston McGarland Bailey [1] (born 4 October 1941), better known by his stage name The Mighty Shadow or Shadow, is a calypsonian from Trinidad and Tobago.

Early life[edit]

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.


He won the Road March in 1974 with "Bassman"(where he also placed second with "I come out to play") and 2001 "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 won the Trinidad & Tobago Hummingbird Medal (Silver) in 2003.[2]

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".

Selected songs[edit]

Shadow's popular calypsoes include:

  • 1974 - "Bassman"; "I Come Out to Play"
  • 1975 - "King From Hell"
  • 1976 - "Jump Judges Jump"; "Children Ting"; "Carnival Scenery"; "Do Good"; "Beat Dem Drums"; "Ladder of Success"; "Don't"; "Without Love"; "Everybody Is Somebody"; "Treat Me Nice"; "Constant Jammin"; "Shift Your Carkass"
  • 1988 - "Tension"; "Crazy Computer"; "The Garden Want Water"
  • 1989 - "Feeling the Feeling"
 1992 - "Dingolay"
  • 1993 - "O What a Life"
  • 1994 - "Pay De Devil"' "Poverty Is Hell"
  • "Snake in the Balisier"
  • 2000 - "Scratch Meh Back"; "What's Wrong With Me"; "Stranger"; "Yuh Looking for Horn"; "HIV"; "Domestic Violence"

He has also done jingles for commercials such as one for the Inland Revenue office of Trinidad and Tobago. Today he is still active but has slowed down.


  1. ^ New Year Honours 2012 The Guardian
  2. ^ "MIGHTY SHADOW". Retrieved 2009-03-31.

Further reading[edit]

  • Mason, Peter (1999). Bacchanal!: The Carnival Culture of Trinidad. Temple University Press. p. 40. ISBN 1-56639-663-8.

External links[edit]