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Shadow

Born Winston Bailey

1941–2018

About Shadow

Calypsonian from Tobago whose 1974 Bassman built a song around a bassline so insistent it changed what soca could sound like, and whose black hat and refusal to explain himself made him the form's great eccentric. He lost the 1974 Road March by a hair and spent decades as the best artist never to win the big crowns, before finally taking Calypso Monarch in 2000. His records are darker and stranger than anything around them. Musicians across the Caribbean treat him as the deepest well in the tradition.