The Jolly Boys grew out of a group called the Navy Island Swamp Boys that formed on 11 April 1945, and often played at Errol Flynn’s parties. This group included Moses Deans on banjo and guitar, Noel Lynch on Guitar and “Papa” Brown on rumba box. After this group split in 1955, Deans and Brown formed The Jolly Boys (a name Errol Flynn is said to have coined) with Derrick “Johnny” Henry on maracas and drum, Martell Brown on guitar, and David “Sonny” Martin on guitar. One of the group’s regular substitutes in this period was percussionist Allan Swymmer, who joined the group as a full member in the 1960s. This group was very popular throughout Port Antonio and earned the reputation of being the finest mento band in the parish.
In the early 1960s, the Jolly Boys’ reputation grew substantially. It performed at hotels and for private parties, often alongside a floorshow/dance troupe. (One of the troupes they typically performed with was led by Albert Minott, at that time an occasional Jolly Boys member and now its current lead singer.) In 1962, the group competed and was a finalist in a national mento band competition held at the Ward Theater in Kingston. The national renown that followed probably also led to international attention. For example, the group auditioned for Jean Farduli, the proprietor of the Blue Angel Supper Club in Chicago (a venue famous for showcasing West Indian music) in 1964. Although it is unclear whether the Jolly Boys passed Farduli’s audition, they did travel to New Hampshire in 1966 for what was the first of several six-month engagements.