Winchester's manager and agent Keith Case said that the singer died at his home in Charlottesville, Virginia, from bladder cancer, reported The New York Times.
Winchester was born James Ridout Winchester in Bossier City, Louisiana. He had 10 years of piano lesson when he was a child. He played organ in local church and later also got interested in playing guitar after listening to songs on radio.
Winchester continued his education at Williams College, majoring in German. He also enrolled in University of Munich for a year, but spent much of his time playing with a rock band. After his graduation, he received draft notice but he left for Canada.