Winston McGarland Bailey, born on 4 October 1941, better known by his stage name The Mighty Shadow or Shadow, was a calypsonian from Tobago. He won the Road March in 1974 with "Bassman" (where he also placed second with "I Come Out to Play") by a record margin, and won again in 2001 with "Stranger", making him the competition's oldest winner. He won the Calypso Monarch contest in 2000 with "What's Wrong With Me" and "Scratch Meh Back". His music used bass more prominently than most calypsonians, of which he said "I did 'Bassman', then I started to use melodic bass lines, not like they used before, and when I performed in the calypso tents in the early days, I had one extra sheet of music, just for the bass." Shadow is also known for his unique dance in which he jumped to the tempo of his music in "skip-rope style" with both feet in the air at the same time. He died on 23 October 2018 at the age of 77.