Wylie Gustafson grew up in Conrad, Montana, where his father raised quarter horses and rode rodeo. The family also had a cattle ranch up on the Blackfoot Reservation by the Canadian border. While raising fine horses, Wylie built a music career with his band, the Wild West. After playing music in Southern California and training horses in Washington State, Wylie resettled on a ranch back in Montana, where his love of cowboy music had started out with his father.