"The Mighty Shadow", Winston Bailey, better known by his stage name The Mighty Shadow or Shadow, was born in Belmont, Port of Spain in Trinidad, but grew up in Les Coteaux, Tobago with his grandparents. He was the first to win both the International Soca Monarch and the Trinidad Road March competitions simultaneously, in 2001 with his song "Stranger." Shadow is the recipient of the Trinidad & Tobago Humming Bird Medal (Silver) in 2003.
Calypsonian Brother Valentino (Ellord Phillip) started his calypso career in 1962 with an appearance at the Big Bamboo Calypso Tent on Park Street in Port-of-Spain. After more than 40 years performing he won his first official title in 2005 when he was crowned Veterans Calypso Monarch at the National Women's Action Committee's (NWAC) inaugural competition