In 1956, Sparrow won Trinidad's Carnival Road March and Calypso King competitions with his most famous song, "Jean and Dinah" (aka "Yankees Gone", a song celebrating the departure of US troops from Trinidad). A live performance of "Yankees Gone" was included in the album "Jump Up Carnival in Trinidad". His prize for winning the Calypso King title was $40. In protest of the small sum (the winner of the Carnival Queen beauty contest won $7,500), he wrote the song "Carnival Boycott" and attempted to organize other singers to boycott the competition. About half of the singers followed, including Lord Melody. Sparrow claims credit for succeeding improvements in the conditions of calypso and steelband musicians in Trinidad, as well as the formation of the Carnival Development Committee, a musicians' assistance organization. Sparrow refused to officially participate in the competition for the next three years, but he continued to perform unofficially, even winning another Road March title in 1958 with "P.A.Y.E." He did perform at the 1957 carnival in the Young Brigade Calypso Tent, where the four songs he performed were recorded and later released on the album "Calypso Kings and Pink Gin".