During the first half of the 1960s, Orbison’s star was on the rise but that wouldn’t last. Tragedy struck in the latter half of the decade and the musician faced one of the toughest, if not the worst, times of his life. In June 1966, Orbison’s wife, 26-year-old Claudette, with whom he shared three young sons, died in a motorcycle accident just outside Nashville, Tennessee. He had been riding ahead of her and was there when a truck hit and killed her (via Newspapers.com). But that wasn’t the end of his suffering.
Two years later, when he was on tour, two of his children died when his home in Hendersonville, Tennessee, burned down. In an odd twist, Orbison sold the lot to Johnny Cash who built a house on the site. Cash’s house also burned down, according to Roy Orbison’s official website. Not long after the deaths of his two sons, Orbison met a German girl, Barbara Jakobs, while on tour in England. They were married in 1969 and had two sons together while raising Orbison’s surviving son Wesley. During the 1970s, Orbison’s career stalled, but by the 1980s, he saw a resurgence in his music.