I Wayne was raised by his aunt and her husband Ansell Collins, a renowned keyboard player. This young artist has been refining his craft since age seven. Coming from a musical family, I Wayne had first made his venture into performance as a student at Greater Portmore High School, joining a local group Vibes Machine. The group, consisting of singers and DJs, used to perform at afterwork parties at popular clubs such as Cactus and Asylum. One night, the artiste was forced to perform alone due to the fact that his bandmates were running late. The response was tremendous, and I Wayne was motivated to perfect his solo act.
In the summer of 2004, I Wayne released Can't Satisfy Her, in the new wave of reggae. The track was reportedly the first roots reggae song to be added to the influential Hot 97 playlist.