Born Von Wayne Charles on July 26, 1972 in Buff Bay, Portland, Wayne's initial singing inspiration came from attending Sunday school, where singing was compulsory, and from his mother who sang in church. As a child Wayne and his family moved all over eastern Kingston, living in areas such as Dunkirk, Franklin Town and Rae Town, home of the weekly Sunday night Reggae/R&B oldies street dance. The exposure to vintage 45's at these dances would provide Wayne with a richer, more soulful vocal approach to a Reggae rhythm track than many of his contemporaries. It was at secondary school where Wayne's thoughtfulness and philosophical nature led to the acquisition of the nickname "Wonder"; young Wayne sang at school, at home, at church and for his friends and wherever he sang, he was encouraged to pursue his craft professionally.

The first producer Wayne recorded for was the legendary creator of dub, the late King Tubby. Wayne voiced three original songs for Tubby, but the one that caught the public's attention was his cover version of British heartthrob Rick Astley's "Never Gonna Give You Up". In 1988, Wayne was devastated by the death of Tubby who was among the most significant influences in his early career. Wayne then linked up with producer Lloyd Dennis voicing the hit "It's Over Now" on the popular "Cover Me" rhythm (titled after the hit by Ninja Man and Tinga Stewart) for Dennis' Pickout label. "That was actually the first song that start to play, like I could go to the dance and look forward to hearing it," Wayne recalls, "so my inspiration grew more from there."

Wayne also recorded his debut album "No More Chance" on the Pickout label. "No More Chance" contained seven original tracks and several obligatory cover versions, reflecting Jamaican producers' preference for recording singers doing American R&B hits. "When I first started out, I got so frustrated, because you carry original material to the studio and they act like they don't even want to hear it," Wayne explains. "They don't accept it. They want you to sing over something that everybody already know. Them don't spend time to hear your creativity or what you try to originate."