Roy Orbison was fascinated with anything with an engine and wheels– motorcycles, go-karts, scooters, and automobiles. He was known to follow a car that he liked and make the driver an offer on the spot. He had a collection worthy of a museum by the late 1960s.

Roy Orbison and his first wife Claudette Frady were married twice– from 1957-64 and from 1965-66. They had their ups and downs. Roy’s touring in 1963 kept him from home and took a toll on their marriage. Claudette began having an affair with the contractor who built their home in Hendersonville, Tennessee. Friends and family blamed the breakdown of their marriage on youth and her being alone and bored while Roy was on the road. When Orbison decided to tour Britain again in the Fall of 1963, she joined him. 

Roy Orbison and Claudette shared a love for motorcycles– she had grown up around them. He credited Elvis Presley with introducing him to motorcycles. Orbison picked up his love of riding motorcycles while on tour, and was competing in scrambles across the pond. While on tour in the UK, he broke his foot falling off a motorcycle in front of thousands of screaming fans at the track– he performed his show that evening in a cast.

Roy Orbison on the CZ of Dave Bickers, 1966 ACU Championship meeting, Hawkstone.

Then tragedy struck on June 6, 1966  when Orbison and Claudette were riding home from Bristol, Tennessee. Claudette was on her motorcycle when she struck a truck that pulled out in front of her and was killed instantly– Roy was riding ahead of her when the accident occurred. The couple had 3 sons. To add to his tragedy– In 1968 their 2 oldest, Roy Jr. 10 and Anthony 6, perished in a fire at the family home in Hendersonville, TN. Their youngest son, Wesley at only 3 yrs old, was saved and raised by his grandparents. The Orbison property was sold to Johnny Cash, who demolished the home and planted an orchard on it. 

Roy Orbison threw himself into his work, but the times and the tastes were a-changin’. It became a  prolonged, challenging period for Roy Orbison’s music career and popularity. The tide of musical taste in America was turning with the British Invasion introducing a new sound, attitude, and look. The counterculture era was close behind the British Invasion, with Jimi Hendrix, Jefferson Airplane, the Rolling Stones, and the Doors pushing Orbison further out of the orbit of relevance. “I didn’t hear a lot I could relate to so I kind of stood there like a tree where the winds blow and the seasons change, and you’re still there and you bloom again.” Orbison still toured and capitalized on smart real estate investments he’d made that provided him financial security for the rest of his life.

Roy Orbison with long-time songwriting partner Joe Melson

The ’80s would relaunch Roy Orbison back into the limelight with a renewed respect and appreciation for his talent and legacy that would cement him as a music legend and an American institution. He was overwhelmed by his newfound popularity and may have literally worked himself to death to capitalize on every opportunity that came his way.

After leaving his thick eyeglasses on an airplane in 1963 while on tour with the Beatles, Orbison was forced to wear his prescription Wayfarers on stage and found he preferred them. He was very shy and wearing sunglasses helped hide somewhat from the attention. Some assumed that the stationary performer was blind. Black clothes and his songs of desperation led to an aura of mystery and introversion. Combined with his tremulous voice in lovelorn ballads aimed at angsty teens, Orbison became a superstar in the early ’60s. 

On December 4th, 1988 Roy Orbison performed at the Front Row Theater in Highland Heights, OH. He returned home to Hendersonville, TN to rest before flying again to London to film two more music videos for the Traveling Wilburys. On December 6, he spent the day flying model airplanes with his sons and ate dinner at his mother’s home in Hendersonville. Later that day, he died of a heart attack, at the age of 52.

Roy Orbison with his brother Sammy

On April 8, 1989, Roy Orbison became the first deceased musician since Elvis Presley to have two albums in the U.S. Top Five at the same time– the Traveling Wilburys album at #4 and his own Mystery Girl at #5. In the United Kingdom, he achieved even greater posthumous success, with two solo albums in the Top 3 in the chart dated to February 11, 1989, Mystery Girl at #2 and the compilation The Legendary Roy Orbison at #3.