Dennis Brown was born on 1 February 1957 at Jubilee Hospital in Kingston, Jamaica. His father Arthur was a scriptwriter, actor, and journalist, and he grew up in a large tenement yard between North Street and King Street in Kingston with his parents, three elder brothers and a sister, although his mother died in the 1960s. He began his singing career at the age of nine, while still at junior school, with an end-of-term concert the first time he performed in public, although he had been keen on music from an even earlier age, and as a youngster was a keen fan of American balladeers such as Brook Benton, Sam Cooke, Frank Sinatra, and Dean Martin.
He cited Nat King Cole as one of his greatest early influences.He regularly hung around JJ’s record store on Orange Street in the rocksteady era and his relatives and neighbours would often throw Brown pennies to hear him sing in their yard. Brown’s first professional appearance came at the age of eleven, when he visited a local club where his brother Basil was performing a comedy routine, and where he made a guest appearance with the club’s resident group, the Fabulous Falcons (a group that included Cynthia Richards, David “Scotty” Scott, and Noel Brown). On the strength of this performance he was asked to join the group as a featured vocalist. When the group performed at a JLP conference at the National Arena, Brown sang two songs – Desmond Dekker’s “Unity” and Johnnie Taylor’s “Ain’t That Loving You” – and after the audience showered the stage with money, he was able to buy his first suit with the proceeds. Bandleader Byron Lee performed on the same bill, and was sufficiently impressed with Brown to book him to perform on package shows featuring visiting US artists, where he was billed as the “Boy Wonder”.