Tragic Facts About Roy Orbison, The Saddest Man In Rock

August 20, 2023 | Eli Artman

Tragic Facts About Roy Orbison, The Saddest Man In Rock

Among the early pioneers of rock ‘n roll music, it is hard to argue that there has ever been anyone more naturally talented than the man who has often been called “The Caruso of Rock”—the late, great Roy Orbison. In a career that spanned more than three decades before his untimely demise in 1988, “The Big O” and his inimitable voice influenced more musical geniuses than most of us can ever even hope to listen to—including the Beatles, Bruce Springsteen, and Bob Dylan, to name just a few. Whether performing a classic rockabilly jam or a heartbreak ballad that touches the soul, Orbison’s operatic voice and its distinctive crying quality never fail to leave even the greatest of singers in absolute awe. Here are 42 little-known facts about the one and only Roy Orbison.

1. I See What You Did There

Let’s start with the elephant in the room—despite the very widespread belief to the contrary, Roy Orbison was not actually blind. It seems that simply because he always performed with dark sunglasses on, a great swath of the public came to the conclusion that the singer was visually impaired—an assumption which, it turns out, was not accurate.

roy orbison

2. What Are the Chances?

So, if he wasn’t blind, what was the real story behind Orbison’s trademark sunglasses-clad look? Well, according to Orbison himself, the reason behind his on-stage appearance was that he didn’t have a manager or stylist, so he just went out there wearing whatever he felt comfortable in. He simply put the shades on one day, felt good performing in them, and never looked back.

Roy Orbison FactsGetty Images

3. A True Legend Never Dies

After his passing, Orbison became the first deceased singer since the one and only Elvis Presley to have ever had two albums hit the top five on the charts at the same time. Both his late-career music and work with the Traveling Wilburys found new fans. It just goes to show that even after one leaves this world, a true legend never ceases to be exactly that.

Roy Orbison FactsGetty Images

4. No Working for the Man for This Kid

As far as he was concerned, Orbison’s entire life path was decided the very moment that his dad first handed him a guitar as a gift for his sixth birthday. He has stated that, from that moment on, “I was finished, you know, for anything else". Orbison’s dad may have only paid for a guitar, but the gift he truly ended up giving the world with that purchase was priceless!

Roy Orbison FactsGetty Images

5. Pretty Car, Driving Down the Street

Orbison had a strong fascination with cars, as well as machines of all kinds. In fact, he loved cars so much that, if he ever spotted a car he liked heading down the street, he would follow it, approach the driver, and offer to buy it from them on the spot. I guess he was perfectly fine with deferring questions such as how the other person would get home, or how he could drive off with two cars at once, for a later time!

Roy Orbison FactsGetty Images

6. Hooray for Hollywood

One of Orbison’s biggest passions outside of music was film. When he wasn’t too busy with his work, he was known to have frequently watched up to as many as three films a day during his spare time.

Steph Curry FactsShutterstock

7. No Attention? No Problem!

Orbison was the only American artist to have a song reach number one in the UK during the entire 68-week period known to music buffs as the “British Invasion". While most other pre-Beatles artists found their popularity suddenly evaporating with the influx of new British rock groups, Orbison continued to dominate the charts as he always had—both in the UK and the US.

Roy Orbison FactsGetty Images

8. Sheer Magnetism

Early in their careers, both Elvis Presley and the Beatles served as the opening acts for Roy Orbison at different points. Hmm, both of the top two acts of the era opening for you. Not bad, I’d say!

When did Elvis die editorialGetty Images

9. Handle With Care

Despite his seemingly effortless stage presence and charisma, Orbison’s biographers have stated that Orbison actually suffered from severe stage fright early on in his career. In fact, this self-conscious fear of his may even have contributed in part to his decision to always wear sunglasses in public.

Roy Orbison FactsWikimedia Commons

10. In Dreams Come True

Orbison was one of the original members of the 1980s rock supergroup the Traveling Wilburys, along with his fellow superstar bandmates, George Harrison, Bob Dylan, Jeff Lynne, and Tom Petty. If that’s not the greatest all-star lineup in history, I don’t know what is!

Roy Orbison FactsFlickr

11. Show Stopper

At the height of his popularity in the early to mid-1960s, Orbison’s presence caused such a stir wherever he went that several of his shows in the UK and Ireland had to be shut down by law enforcement because he was being physically swarmed by excited female fans who couldn’t keep their hands off him. It got so bad that officers had to come on stage and start physically dragging the adoring intruders off of him.

Even Justin Bieber doesn’t know what that level of fan attention feels like!

Roy Orbison FactsGetty Images

12. It’s Over?

Due to frustrations over what he felt was a lack of fair treatment by his recording studio, Roy Orbison briefly quit his performing career in 1958. Lucky for all of us, this hiatus only lasted about seven months when all was said and done.

Roy Orbison FactsGetty Images

13. Paint It, Black

As central as Orbison’s dark hair was to his popular image, it turns out that it was not really his natural hair color. His hair was actually a much lighter shade of brown, and he routinely dyed it black to fit in with the rest of his “dark” image.

Roy Orbison FactsShutterstock

14. In Mourning

Although Roy Orbison initially tried to deal with the loss of three of his closest family members by throwing himself into his work, he was ultimately so devastated that, by late 1968, he had all but completely withdrawn himself from the public spotlight for a very long period of time. He spent the entire rest of that year at home, struggling to cope with his grief.

Roy Orbison FactsPixabay

15. Second Chance

Despite having been a star primarily in the 60s, Roy Orbison experienced a rare and surprising resurgence in popularity just before the end of his life in the late 1980s. Not only was he a part of the Traveling Wilburys supergroup, several of his songs covered by high-profile popular artists at the time. He also recorded a brand new original song called “You Got It,” which became his first top ten hit in almost 25 years.

Sadly, although he had been enjoying his sudden renaissance of new attention, Orbison passed on that same year and didn’t live to see just how popular this song would become.

Roy Orbison FactsWikimedia Commons

16. More Popular Than the Most Popular?

At the height of his popularity, Orbison was so well-loved by his fans that none other than The Beatles practically got heckled off the stage to angry chants of “We want Roy!” one night when they attempted to take the stage following a 1963 performance of his in the United Kingdom. After a whopping fourteen encores, John Lennon and Paul McCartney felt that their turn to perform had arrived—and they had to physically restrain Orbison from retaking the stage again!

Roy Orbison FactsGetty Images

17. Third Time’s a Charm

As popular as Orbison’s musical style turned out to be, one of his doubters in the early days was none other than himself! Orbison had tried to record the song “Ooby Dooby” on two separate occasions, but never found success with it. Nevertheless, despite not thinking that it would lead anywhere, he eventually agreed to record the song for a third time at the insistence of legendary producer Sam Phillips.

Orbison hesitated every step of the way, and still felt unsure about the project even on the very day when the recording was made. Well, history has shown that the Big O should never have doubted himself—the song became his first major hit, and was the beginning of an epic musical career.

Hoaxes FactsShutterstock

18. A King’s King

Elvis Presley, as in the man who the music world refers to as the “King,” once referred to Orbison as “the greatest singer in the world". How’s that for an impressive reference!

Roy Orbison FactsGetty Images 

19. Mercy!

Orbison’s most famous song of all time, “Oh Pretty Woman,” was written from start to finish in under 40 minutes. He and his writing partner, Bill Dees, were in the midst of working on “It’s Over,” one of his eventual signature songs when they were very rudely interrupted by Orbison’s wife Claudette—who entered the room to let her husband know that she was heading out.

Orbison asked if she needed any money, to which Claudette replied: “A pretty woman never needs any money!” Inspiration immediately hit and the rest, as they say, is history.

Roy Orbison FactsWikimedia Commons

20. Free Fallin’

Roy Orbison once fell off his motorcycle and broke his foot right in front of a large crowd of shocked fans. Despite this setback, he didn’t miss a beat. He still performed a scheduled show that very evening, cast on his leg and all.

Roy Orbison FactsWikipedia

21. Encore Performance

Despite his early demise, 1988 was not the last the world saw of this music legend. In late 2017, Orbison’s image and voice were brought “back to life,” so to speak, as video and audio of his performances were used to produce the first-ever hologram concert tour. In other words, fans had the opportunity to attend concerts where a life-sized image of Orbison appeared on stage and put on an entire show for them as if he was really there in person.

The technology was so sophisticated and realistic that it actually made Orbison’s son tear up at what felt to him like the first time in 30 years that he had seen his dad live on stage.

Roy Orbison FactsGetty Images

22. Close Shave

Orbison suffered a major health scare while vacationing in Hawaii in 1977 and had to undergo a triple coronary bypass procedure to unblock his arteries. Thankfully, he received excellent medical care and made a full recovery—making the epic comeback era of his musical career possible.

Florence Nightingale FactsShutterstock

23. Nothing to Be Scared Of

Unbeknownst to many, the rhythm behind Orbison’s 1961 hit song “Running Scared” is actually a rock ‘n roll adaptation of the famous classical piece “Bolero”—which proved to be a perfect fit for him to show off the operatic capabilities of his singing voice.

Millie Bobby Brown factsPixabay

24. Accidental Genius

There are few lines as distinctive and iconic in a rock song as Orbison’s exclamation of “Mercy!” over the famous riff in the song “Oh, Pretty Woman". Believe it or not, this epic line was one of the few that did not come to be as a result of Orbison’s brilliant songwriting abilities. On the contrary, Orbison just happened to shout “Mercy!” when he realized that he couldn’t hit the high note he had originally intended to occupy that spot in the song.

It was an extremely rare occurrence for the man known all over the world for his unparalleled ability to hit just about any and every note there is.

Roy Orbison FactsFlickr

25. Hopeful

Another one of the most distinctive parts of the song “Oh, Pretty Woman” is Orbison’s playful growl at the end of the second verse. Like his “mercy” cry, this too came to Orbison’s mind in a very unlikely way. Probably due to his love of film, the singer had been watching a Bob Hope comedy movie around the time he was working on this song, and heard the comedian let out a silly growl that he just couldn’t forget.

He imitated the noise as best he could, and eventually worked it perfectly into the song—adding yet another iconic and unforgettable feature to this classic hit.

Roy Orbison FactsGetty Images

26. Strawberry Forkfuls Forever

Orbison once had a meal fed to him by John Lennon and Ringo Starr. Yes, you read that correctly, they’re actually feeding him in the photo. Now, to have a Beatle feed you a meal means you’re probably pretty darn important—but two Beatles?? That means you’re a legend!

Roy Orbison FactsGetty Images

27. Friends in High Places

Many people have observed that Orbison had an extremely unique and distinctive singing voice. Well, those people are not imagining it. In musical terms, what made Orbison’s vocal abilities so rare and unlike most other singers in the rock and pop worlds was that his vocal range extended to both extremely high and extremely low notes—all in perfect pitch.

For example, despite being a male, his voice was able to effortlessly hit notes at least a full octave higher than even the average high-pitched female singing voice can go. With talent like that, it’s no surprise that even musical legends who had seen it all still found themselves in utter awe at Orbison’s abilities as a singer.

Roy Orbison FactsPixabay

28. What’s in a Name?

No less than a whopping nine Hollywood films have been titled after Orbison songs over the years—Pretty Woman, In Dreams, and Only the Lonely being just a few examples. It seems this guy must have had a way with words or something!

Molly Ringwald FactsPretty Woman, Buena Vista Pictures

29. Keep On Rocking

Although Orbison’s vocals are featured prominently in the Traveling Wilburys song, “End of the Line,” the music video for the song was unfortunately not filmed until after his sudden demise, which happened shortly after the song was recorded. As a result, the group decided to pay tribute to their beloved bandmate by featuring images of a peaceful rocking chair swaying back and forth with a guitar on its seat each time that Orbison’s vocals were heard.

It was a touching tribute from his fellow musical icons.

Roy Orbison FactsShutterstock

30. In High Demand

While Orbison was still just a high school student, the band that he had started in his spare time was once offered a full $400 to play at a local school dance—a massive payout for a kid to be paid for a single gig, especially back in those days!

Spice Girls FactsShutterstock

31. The Left Side of the Aisle

Ever since childhood, Orbison’s favorite singer and music idol was the classic country star Lefty Frizell. Frizell’s “[mumbled] syllables” style of singing was one of Orbison’s earliest musical inspirations—and he never forgot the impact it had on him. Decades later, as part of the Traveling Wilburys, Orbison used the name “Lefty Wilbury” as his alter ego within the group, as a tribute to the man who first sparked his interest in music all those years before.

Roy Orbison FactsWikimedia Commons

32. Jack of All Trades

Although the rock ‘n roll genre is where Roy Orbison eventually found his home, it wasn’t always his path. With his first band, the Wink Westerners, his repertoire consisted solely of old-time country and jazz standards.

Roy Orbison FactsWikipedia

33. Cashing Out

After the tragic house fire that killed two of Orbison’s sons, the singer no longer felt comfortable owning the property that he once called home—and he decided to put it up for sale. Interestingly enough, of all the prospective homebuyers who were looking for a place at that particular time, it ended up being none other than country music legend Johnny Cash who purchased the property from him.

Cash eventually tore down Orbison’s former home and planted an orchard on the site.

Roy Orbison FactsGetty Images

34. Eight Is Great!

Orbison’s formal musical career began at the tender age of just eight years old—when he was invited to sing on a local radio show in his native Texas. Little did those lucky listeners know that day that they were witnessing the beginning of one of the greatest chapters in rock ‘n roll history!

Roy Orbison FactsShutterstock

35. Can’t Help Falling in Love—with Motorcycles

Roy Orbison had a love of motorcycles that stayed with him for his entire adult life. How did he get into this interest of his, you ask? Turns out he was first introduced to motorcycles by none other than the king himself, Elvis Presley!

Roy Orbison FactsWikimedia Commons

36. Through Thick and Thin

Although Orbison spent the second half of his life mourning the loss of his beloved wife, Claudette, things weren’t always 100% smooth between them. In fact, their relationship got so rocky at one point in 1964 that the couple briefly divorced. Nevertheless, they quickly reconciled their differences and got remarried a mere ten months later.

Worst Ways They’ve Been Dumped FactsShutterstock

37. Nice to Meet You!

In the early 1960s, before the Beatles had become famous in the US, Orbison initially responded to the news that he would be touring with a group of that name by asking “What’s a Beatle, anyway?” Unbeknownst to him at the time, a young John Lennon had overheard that exchange. He approached Orbison, tapped him on the shoulder, and matter-of-factly stated: “I am".

Roy Orbison FactsGetty Images

38. The Slowest Film Alive

Encouraged by the string of hit films that Elvis Presley had starred in earlier in the decade, MGM decided to try featuring Orbison in a 1967 comedic film of the same style, The Fastest Guitar Alive—in which Orbison portrayed a Civil War-era spy who could shoot bullets out of a guitar. Unfortunately for all those involved, the film was such a colossal flop that the studio never even bothered to produce a single one of the other four movies in the series that they had originally promised to follow it up with when they had first signed Orbison as an actor.

Samuel L. Jackson factsShutterstock

39. I’ve Got a Secret

While taking some time off in 1969 to grieve the losses of his wife and sons, Roy Orbison recorded a secret album expressing his grief as a way to help cope with the devastating losses. Although the few people who had known about it long believed it to have been lost forever, fans were amazed to learn that the recordings were recently discovered by Orbison’s living sons.

The album was released to the public for the first time in 2015.

Roy Orbison FactsWikimedia Commons

40. Crying Over You

Not every aspect of Orbison’s life revolved around the joy of the musical spotlight. Unfortunately, he was also a man who often found himself struck by tragedy. Among the most heartbreaking tragedies that Orbison ever had to deal with was the sudden loss of his wife, Claudette, in a 1966 motorcycle crash. The couple was riding together while on vacation when a truck suddenly pulled in front of them—causing the fatal impact.

Claudette passed on in her husband’s arms at the age of 25.

Roy Orbison FactsGetty Images

41. When Tragedy Strikes Twice

The loss of wife Claudette was not the only major tragedy that struck the Orbison family during the late 1960s. Just two short years following the fatal motorcycle accident, a fire broke out at Orbison’s home while he was away on tour in the United Kingdom. His two eldest sons, Roy Jr. and Anthony, lost their lives in the disaster. Needless to say, Orbison was utterly devastated.

A man stands in front of his burning house and looks with horrorEvGavrilov, Shutterstock

42. It’s Always Better to Be Safe Than Sorry

It was sad enough that Roy Orbison passed on suddenly of a heart attack at the young age of 52—but it gets even more tragic. His friends recall that he had been openly complaining of chest pains for months leading up to that day, but admittedly never got around to making a doctor’s appointment. Likely because he was too busy with his new musical projects, he tragically put off making that call until it was too late.

Who knows where the newfound revival of his career could have taken him if it had been able to go on for longer.

Roy Orbison FactsShutterstock

Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18

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