Joseph Winston Sterling was born on 24 June 1956 in St Mary, Jamaica. He took his stage name from the Clint Eastwood Western The Outlaw Josey Wales and automatically “The Outlaw” became his nickname alongside “The Colonel”. Sterling’s first performance as a DJ was in 1977 with The Roots Unlimited Sound System. Here, he often sparred with Burro Banton and later on performed over U-Roy owned King Sturgav Sound System.  Sterling gained more popularity when he performed over Henry ‘Junjo’ Lawes Sound System where he recorded singles such as “Bobo Dread” and “Leggo Mi Hand”. “Let Go Mi Hand” became his breakthrough single which established his career as a recording artist. In 1983, Sterling recorded his debut album titled “The Outlaw Josey Wales”.