Shadow
(Andrea De Silva Viarruel @Silva Image)

An icon in Caribbean music, a legend within the calypso art form and a powerful force in shaping calypso’s up-tempo descendant soca, Winston “Shadow” Bailey died at Mount Hope Hospital, St. Joseph, Trinidad, on Oct. 23, following complications from a stroke. He was 77.

An enigmatic musical figure, Shadow was typically attired in an entirely black ensemble covered by a cape or waistcoat and topped with a hat, all suggestive of his calypso moniker. Shadow would alternate his sung vocals with hypnotic chanted choruses, and further punctuated his onstage delivery by jumping in place. The distinctive calypso and soca rhythms he chose were characterized by heavy, unrelenting bass lines as heard on such classic compositions as “Dingolay,” a poetic ode to the power of music; “Tension,” a statement on corruption in the soca business; the deeply affecting commentary “Poverty Is Hell,” and the song that first earned Shadow attention throughout Trinidad, 1974’s “Bassman.” A recipient of countless awards throughout the Caribbean Diaspora including The Hummingbird Medal, one of the highest civilian honors bestowed in Trinidad and Tobago (T&T) for his contributions to the arts, Shadow was scheduled to receive an honorary doctorate from the University of the West Indies, Trinidad, for his lifelong contributions to the nation’s music; that recognition will be conferred posthumously on Oct. 27.

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  • Shadow - D'Hardest

    This stripped down dance-floor version of D'Hardest has been a secret weapon for years. Shadow told us that he went to Studio 54 right after they finished recording this song someone convinced the DJ to play it and the the crowd went crazy. Island Electronic

  • Shadow gets his doctorate...Oct 27, 2018

    IN DADDY’S HONOUR: Sharlan Bailey displays the Doctor of Letters honorary degree which he received on behalf of his father Winston Bailey (Shadow) at The University of the West Indies’ Presentation of Graduates 2018 held at UWI Spec, St Augustine yesterday.

    FOUR days after his sudden death, calypso legend Shadow (Winston Bailey) has been conferred with an honorary doctorate from The University of the West Indies (UWI).

    Shadow was scheduled to accept the Doctor of Letters, Honoris Causa, for his contributions as a musical composer at UWI’s graduation ceremony yesterday.

    https://www.trinidadexpress.com/news/local/shadow-gets-his-doctorat...

    2959993268?profile=original

  • Shadow represented a different dimension in Trinidad music, he was a true original, a calypso and soca rock star.”

    PATIENCE has its REWARDS...never too late.

    Shadow - Dey Sticking "2015 Trinidad Calypso"

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