In his early years he performed wearing all black, with a large hat covering part of his face. 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'. He chose the stage name 'Shadow' (he didn't use 'Mighty' himself) after coming across some workmen digging a road while he was walking.

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. Īt the age of 16 he moved back to Port of Spain, where for a time he was homeless while trying to established himself. He started singing calypsos at the age of 8. Winston McGarland Bailey OBE, HBM, DLitt (4 October 1941 – 23 October 2018), better known by his stage name The Mighty Shadow or Shadow, was a calypsonian from Tobago.īailey was born in Belmont, a suburb of Port of Spain in Trinidad, but grew up in Les Coteaux, Tobago, with his grandparents.

The mighty vibe