Sokah2Soca readers, get ready for an exciting journey as we celebrate the legends and luminaries who have shaped Caribbean music. In our new feature series, we’ll spotlight the artists whose creativity and talent continue to inspire generations. Today, we proudly begin with none other than the legendary Winston Bailey, better known as The Mighty Shadow—a true musical innovator and cultural icon.
The Mighty Shadow, born Winston Bailey, was a visionary calypsonian known for his unique style, blending calypso with a personal touch. His music, characterized by haunting basslines, hypnotic rhythms, and themes of introspection, fantasy, and social commentary, defied the norms of his time. His unique signature, "Bassman," "Dingolay," and "Poverty is Hell," defied the norms of his time. His legacy as one of Trinidad and Tobago's most innovative artists will live on forever.
Caribbean Insight TV YouTube Notes: The Truth about Shadow's Dream
Uncover the truth about Shadow's dream in this insightful look at his career and impact on the calypso world. Learn about his rivalry with Mighty Sparrow and Lord Kitchener, as well as his iconic Road March win in 1974.
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Winston McGarland Bailey (October 4th, 1941–23rd, October 2018), Bailey was born in Belmont, a suburb of Port of Spain in Trinidad, but grew up in Les Coteaux, Tobago, with his grandparents. He started singing calypsos at the age of 8.
In 1970 he performed as part of the chorus in Mighty Sparrow's 'Young Brigade' calypso tent, and by the following year he had begun to establish himself as a calypsonian in his own right. He won the Road March in 1974 with "Bassman" (where he also placed second with "I Come Out to Play") by a record margin and won again in 2001 with "Stranger," making him the competition's oldest winner. [2] He won the Calypso Monarch contest in 2000 with "What's Wrong With Me" and "Scratch Meh Back."
He was the second calypsonian to win both the International Soca Monarch and the Trinidad Road March competitions simultaneously, a feat he accomplished in 2001 with "Stranger." He rivaled fellow calypsonians Mighty Sparrow and Lord Kitchener after winning the Road March in 1974.
He died on 23 October 2018 at the age of 77 at Mount Hope Hospital in St. Joseph, after suffering a stroke two days earlier.
Artist: SHADOW
Featured Songs:
- Columbus Lie
- Obeah
- If I Coulda
- Jump Judges Jump
- Pay De Devil
- Poverty Is Hell
- Pandora
- Feelin The Feeling
- Dorothy
- Soucouyant
- What is Life
- The Garden Want Water
- Tension
Featured Steelband: Invaders
SONG: Bassman
Archival Materials
- Courtesy of CITV library
- Courtesy of TTT
- Courtesy of WE TING 2
- Courtesy of CTV
- Courtesy of TV 4
- Courtesy TV 6
- Courtesy of 94.1
- Courtesy of Visual Arts Productions
- Courtesy of GBTV
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Production Notes/Music Credits:
Review article: The Truth about Shadow's Dream
Origin: Trinidad, Republic of Trinidad & Tobago
Genre: Calypso/Soca/Shadow Music
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