The Merrymen's career spans four decades, from the early 1960s to the 2000s. At their height they were popular not just throughout the Caribbean, but they had also managed to reach the number one spot on the charts of several European countries.
Their trademark sound is an upbeat form of calypso, reminiscent of what was popular in the Caribbean in the late 60's and early 70's, that samples liberally from latin, funk, tuk and spouge musical styles. Lead singer Emile Straker's whistling is one of the most distinctive components of their sound, and often serves as the primary focus of the musical interludes in their songs. They have produced several memorable covers in this style, including versions of "Island in the Sun" (originally by Harry Belafonte), "Jamaica Farewell", "Hot Hot Hot" and "Mary's Boy Child".