Shadow (calypsonian)

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Winston Bailey, better known as Shadow, is a calypso musician from Trinidad and Tobago. Bailey was born in Trinidad but grew up in 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 had hits beginning in 1974 like

  • I Come Out to Play
  • King From Hell
  • What is Life
  • Crazy Computer
  • Jump Judges Jump
  • Children Ting
  • Dingolay
  • Poverty is Hell
  • Tension
  • Pay de Devil
  • Snake in the Balisier

He also did jingles for commercials like the inland revenue of Trinidad and Tobago as well. Today he is still active but has slowed down.

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