Bailey was born in Belmont, a suburb of Port of Spain in Trinidad, but grew up in Les Coteaux, Tobago, with his grandparents.

[5] 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".

"[4] Shadow' innovative use of the melodic bassline in "Bassman" was a harbinger of things to come with the emerging soca music style that would transform calypso in the mid-1970s.

[4][8] 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".

[12] On 27 October 2018, the University of the West Indies conferred on Bailey the Degree of Doctor of Letters (DLitt) Honoris Causa for his contributions as a musical composer, an award he had been due to receive before he died.