Hailing from Salem, Herman "Cupid" Francis has been a mainstay in the Montserrat Calypso Monarch competition since the mid-1980s. In 1985, many believed he was ready to win the crown with his popular song "Long Grass", but he couldn't overcome the juggernaut called Justin "Hero" Cassell, who won with "Who is de Man" and "Greedy Merchants". In 1986, Cupid returned with a vengeance with "50,000 Chinese", but again Hero was the champ with "Body to Body" and "I'm Underage". Cupid would go on to finish first runner-up several times before finally hitting paydirt in 1998 with "How Many More", although that competition featured only one round. In 2002, Cupid sang the politically scathing "Sniper in Town" but was kept at bay by Joseph "Pops" Morris and his emotional ballad "Thank You." In 2004, Cupid finished third in the competition but earned an award for the Best Political Commentary with "Rat in De Sugar", a metaphor-driven tune addressing prostitution in Montserrat. In 2005, he again garnered the Best Political Commentary prize for "Voices".

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