“Everyone who saw a Roy Orbison show live probably shed a tear at one point during the concert,” says the late musician’s son Roy Orbison Jr.

He remembers attending one of his dad’s concerts as a kid, sitting near the front and crying at the beauty of his father’s voice. When the singer of “Crying” and “Only the Lonely” saw his son’s tears, he sent a stage manager over to tell him to sit a little farther back. Seeing his son cry was too much for the performer, who had lived through enough heartbreak that his emotions always hovered near the surface.  As Roy Jr. tells Closer, “He was a very sensitive father, just like he was as an artist.”

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People remember Roy, who died of a heart attack at 52 in 1988, as “the Big O,” the enigmatic singer dressed in black with dark sunglasses, whose soaring voice ranged from baritone to tenor. He was as compelling as he was mysterious. “He’d have this strange presence. He’d walk in [a room] and it was like a ghost walked in,” says Roy Jr., who recently appeared on Bravo’s Below Deck Mediterranean. Perhaps that’s because Roy himself felt haunted by tragic losses he’d worked to put behind him.

By age 20, Roy, who was raised in Texas, was recording at Sun Records in Memphis, Tennessee, along with his hero Elvis Presley and his lifelong friend-to-be Johnny Cash. A few years later, “Only the Lonely” charted at No. 2 and he became a star with other songs like “Pretty Woman.” “I liked the sound of [my voice],” Roy once said. “I liked making it sing, making the voice ring.”

But personally, Roy struggled. “He was addicted to the road,” Roy Jr. says. His absence put a strain on his marriage to first wife Claudette Frady, with whom he had three sons, and they divorced in 1964.

They eventually reconciled, only for her to die “in his arms,” Roy Jr. explains, when Claudette’s motorcycle struck the door of a pickup truck. On tour 18 months later, Roy learned his two eldest boys had died in a fire that destroyed his Tennessee home. “He got knocked down in quick succession,” Roy Jr. says. But his father remained stoic: “He would’ve said he did not suffer more tragedy than other people.”

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Before his sons’ deaths, however, he’d met Barbara Jakobs. “She came into his life at a time where he was not in good shape, and she just breathed fresh air into it,” Roy Jr. shares. They married and started a new family, and Roy “just went forward. He never looked back.”

Despite his struggles and the ups and downs of his career — which lagged in the ’70s but revived, culminating with the Traveling Wilburys, his Grammy-winning band with George Harrison, Tom Petty, Bob Dylan and Jeff Lynne — Roy remained optimistic. “He was a lot
of fun and lived a great life,” says Roy Jr., who is working on a biopic about his dad. “He collected cars. He drove motorcycles. He played a lot of practical jokes.”

And Roy’s legacy will continue: “There are still some unreleased songs,” Roy Jr. tells Closer. “We’re doing the Orbison Museum. There’s not a day that goes by that I don’t see him or hear him or think about him, and that is a blessing. I just miss the guy.”

— Lisa Chambers, with reporting by Diana Cooper