Mighty Shadow, born Winston McGarland Bailey in 1941 in Trinidad and Tobago, was a legendary calypsonian known for his unique style, haunting melodies, and socially conscious lyrics. Emerging in the 1970s, Shadow's music stood out for its deep, bass-driven sound and his distinctive voice, which brought a mysterious and philosophical edge to calypso. He became famous for hits like "Bassman," "Poverty Is Hell," and "Dingolay," which showcased his ability to blend humour, social critique, and Caribbean rhythms. Shadow won the Road March title twice and claimed the Calypso Monarch title in 2000, reflecting his enduring influence on the genre. He remained an innovative and beloved figure in calypso until his death in 2018, remembered for his eccentricity, creativity, and contributions to Caribbean music.