Memory Music Series

Winston McGarland Bailey, HBM, DLitt (4 October 1941 – 23 October 2018), better known by his stage name The Mighty Shadow or Shadow, was a calypsonian from Tobago. 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.

At the age of 16 he moved back to Port of Spain, where for a time he was homeless while trying to establish himself.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 chose the stage name "Shadow" (he didn't use "Mighty" himself) after coming across some workmen digging a road while he was walking. One of the workmen was in a hole below the road surface and the others were calling him "Shadow", and Bailey said: "I felt like they was calling me". In his early years, he performed wearing all black, with a large hat covering part of his face.

The Guardian newspaper, speaking of Shadow's stagecraft, argued that he had "a persona and outlook that stood in dramatic contrast to the classic bravura of the typical calypsonian, one that might have been expected to generate either bemusement or scorn in his native Trinidad and Tobago", and yet noted that on the contrary his stage presence and music "proved so original, so eerily amusing and so engaging that [he] quickly came to be hailed as one of the greats."

Video derived from: Ria Khodai. (2022). Facebook.com. https://www.facebook.com/ria.khodai/videos_by

Notes derived from:

(2025). Youtu.be. https://youtu.be/x8Cfko7glDc?si=f8gD_DYcxPEm5E1o