Although 17 different calypsonians have captured the crown in Montserrat, Cepeekee is one of only six to win the title three or more times (Hero, Arrow, Reality, Warrior and Kenzie are the others). Cepeekee's ascent began in the mid-'80s. In 1985, he sang the popular "Dis One Ya Hard", and while many thought he was a shoo-in for the Road March, he lost out to Vulture and "Action". Cepeekee's first crown came in 1987 with "Help Me Out" and "Turn Me On". The following year, many thought he would successfully defend the title after he gave an emotional performance of "It's a White Man's World". When Hustler was announced the winner, many in the audience showed their displeasure by flinging bottles and stones. Cepeekee bounced back, however, and won in 1990 and 1999. His key song in 1999 was "Payoff", a song recounting a scandal involving a key government figure. Cepeekee, an Amersham native, has since backed away from the competition and chosen to dedicate time to his band, which provided all the musical backing for the 2004 and 2005 calypso monarch competitions.