Josey Wales (born Joseph Winston Sterling, October 9, 1958, in St. Mary, Jamaica) is a Jamaican dancehall singer. He has been called, along with Brigadier Jerry, Yellowman and sound system partner Charlie Chaplin, one of the best Jamaican dancehall deejays of the 1980s. Wales is named after the 1976 Western movie character from The Outlaw Josey Wales, played by Clint Eastwood, and subsequently nicknamed "The Outlaw".
His career began in the late 1970s, first starting as a deejay on the Roots Unlimited sound-system where he often sparred with Burro Banton, and later performing over U-Roy-owned King Sturgav sound system. He gained even more popularity in the early 1980s performing over Henry "Junjo" Lawes's Volcano sound system, and recording singles such as "Bobo Dread" and "Leggo Mi Hand" for Lawes' label of the same name, as well as later hits for George Phang's Power House label, most noticeably "Undercover Lover".
He was shot and robbed in a Kingston bar in 1997, an incident that he dealt with in the country and western song "Bushwacked". He survived the robbery, and after his discharge from a hospital, he went to the United States and bought an ambulance to donate for the Kingston Public Hospital.
He appeared in Shaggy's "Bad Man Don't Cry" video, and by 2014 had begun recording new material.
In October 2017, he was awarded the Order of Distinction by the Jamaican government.
