With thick, dark sunglasses and a lofty presence, Texas-born singer-songwriter Roy Orbison became one of the ‘1960s most treasured artists, both in America and in the UK. In fact, his presence was so large it rivaled that of The Rolling Stones and even Elvis at times, especially on the Billboard charts. Timezone-hopping hits like ‘Only The Lonely’ gave him an international focus. And his mysterious, pensive image only added to the legend that was and still is, “The Big O.”
His haunting, soulful vocals fit perfectly with sad songs. But the songwriting genius always colored his tracks with a hopeful tint. It was irresistible to listeners, who related to the wide-open, sometimes operatic recordings that allowed them to feel everything all at once, with Orbison gently directing them towards the final resolution.
After passing away suddenly in the late ’80s, countless artists who were influenced by him, like Bono and Bob Dylan, carried on his torch by offering up their own renditions of his songs. His estate also continued to put out a wide array of Orbison’s work posthumously. With a decade-defying career and golden pipes that could make grown men cry, we take a look at the best Roy Orbison songs below.
14. Ooby Dooby
Part doo wop, part rockabilly, ‘Ooby Dooby’ is an early rock n’ roll classic originally written by Dick Penner and Wade Moore. The first single Roy recorded with his band in the mid. ’50s, the Teen Kings, it would go on to be their first hit during their short-lived stint with the famous Sun Records (he would go on to have much more recording success with Monument Records). With a fun beat and dazzling electric guitar riffs, “ooby dooby” is in reference to a type of flirtatious dance that involved a lot of suggestive hip-shaking. The song’s fast pace and sometimes-nonsensical lyrics made it a classic 1950s rock piece. As exciting as Orbison’s early version is, rock legends Creedence Clearwater Revival kicked things up a notch when they recorded a rendition of their own in 1970. It’s one of their more eclectic tracks, despite being on their hit-heavy album Cosmo’s Factory. Frontman John Fogerty reimagined the track with a more swampy production and wailing guitar parts straight out of the powerfully electrified ’70s.
13. Dream Baby (How Long Must I Dream)
Written by songwriter Cindy Walker, who penned many popular songs throughout her musical career, ‘Dream Baby’ was a huge hit for Orbison in both Australia and across Europe. Released in the early ’60s, many male-fronted bands focused on a macho, bad-boy image. But for Roy, especially with songs like this one, he went in the opposite direction, creating a stoic yet vulnerable performance experience that was both refreshing and eagerly embraced by audiences. His vocal ability is apparent with this single. You can even hear hints of Elvis Presley’s buttery vibrato and Buddy Holly’s vocal “yips” or “hiccups” in Orbison’s delivery, two fellow artists who saw major success just before him in the ’50s. A romantic track that features a protagonist talking about how he can’t get his flame out of his head day or night, the song had major crossover appeal. Country star Glen Campbell recorded it in the ’70s, and his version broke into the top 10 on American country charts, and even the top 5 on Canadian country charts. Other major artists to cover the tune include The Beatles, Waylon Jennings, and Jerry Lee Lewis.
12. Running Scared
With a distinct operatic feel, ‘Running Scared’ comes off big and dynamic on the recording, made this way on purpose by Orbison’s Nashville sound engineer Bill Porter. Part of a recording production group known as “The A Team,” with Roy by their side they managed to lead the charge for an early “rock opera” style trend that would ultimately be championed and reinvented by iconic groups like Queen. This number 1 single on American charts marked Roy’s transformation from his rockabilly sound during his Memphis Sun Records days to that of pop-rock when he moved on to Monument Records. With pensive downbeats followed by staccato-like bouts of silence, this stop-and-start rhythm to the instrumentation adds to the drama of Orbison’s vocal performance. Though the song seems to be a bit of a heartbreak downer, the story has a happy ending, with our protagonist getting the girl.
11. Handle With Care (with the Traveling Wilburys)
A simple recording session at Bob Dylan’s California home turned into the forming of one of music’s greatest super groups of all time, The Traveling Wilburys. For their first single released in ’88, ‘Handle With Care,’ Roy Orbison’s moody, expressive vocals delicately handle the chorus while buddies like George Harrison and Tom Petty hold down verses and harmony. A song about needing a more loving partner the next go ’round after getting out of a complicated relationship, the tune would set up a long line of popular releases for the band. Unfortunately, Roy would only contribute to their first album before suddenly passing away from a heart attack just two months after its release. The Traveling Wilburys would go on to record another batch of tunes together, making sure to pay homage to their late friend in music videos with an image of a lone guitar propped up in a chair for their song ‘End of the Line.’
10. It’s Over
A contemplative piece driven by a drum beat that seems to usher listeners forward in a march, ‘It’s Over’ took the top spot on UK charts in 1964, beating out other popular acts like The Beatles and The Rolling Stones. Though the single is about realizing things can come to an end without people even knowing it when it happens, Orbison’s expressive vocals and the production’s operatic, uplifting sequence in the same vein as ‘Running Scared’ gives it an empowering feel. Some 55 years later, songwriting giant Morrissey released a towering rendition of ‘It’s Over’ on his album featuring his favorite tunes, California Sun. Morrissey’s soft, crooning voice is perfect for the cover, and glittery production gives it a grand ’80s vibe. It’s a must-listen take on an Orbison masterpiece.
9. She’s a Mystery to Me
Recorded just a couple months before he passed away, ‘She’s a Mystery to Me’ is a song written by U2 frontmen, vocalist Bono and guitarist “the Edge.” Inspired by a dream he had while falling asleep to the soundtrack of the noir film Blue Velvet, when Bono woke up humming the melody he thought for sure it was in one of the CD’s songs. After realizing it wasn’t, he took it to the band where they continued to work on it while on tour. Just after coming up with the tune, in a serendipitous turn of events, Roy visited Bono on their tour (Roy had a tendency to intuitively show up where he was needed). While visiting Bono, the U2 bandmate introduced him to the track, and Orbison recorded it in September 1988. Appearing on the posthumous album, Mystery Girl, inspired by the song’s title, it proved to be a gem for critics and fans alike, who felt the haunting ballad kept Orbison’s spirit alive after his sudden passing.
8. California Blue
With hints of country and bright acoustic guitar, Heartbreakers frontman Tom Petty and Electric Light Orchestra’s Jeff Lynne helped Orbison write this starry-eyed track. Hints of melancholy strike the notes as he sings about wondering when he’ll make his way back to someone (or possibly something), but there is still a hopeful tone to the message. This dichotomy is one of the reasons why Roy’s songwriting and performance were so relatable and engaging. Despite its light, airy pop vibe, the lyrics are full of yearning, and fans of Orbison have long related to the tune’s open-ended meaning, giving way for many people to feel the song represents something to them individually, whatever their needs may be at the time (from mourning and moving on to celebration and the start of something new).
7. Blue Bayou
When you hear the title ‘Blue Bayou’ you may automatically think about Linda Ronstadt’s chart-topping hit. But Orbison was actually the one who wrote the dreamy, beachy track and released it first. While his didn’t chart nearly as high as Ronstadt’s signature version, it has become an integral part of his original music canon over the years. When Orbison wrote it, he was on the road, in the middle of one of his many successful tours. Naturally, he was missing home, but he was also happy doing what he loved. This duplexity is what comes out in this single, which paints a vivid picture of a slow-paced vacation spot the protagonist is yearning for as he reflects on the absence of his one and only. The song’s story finds him working hard to get back to that picturesque spot (perhaps this represented “home” in Roy’s real life). A particularly enjoyable layer to this recording is the song’s gentle harmonica, which gently rocks listeners back and forth as the wistful tale plays out.
6. I Drove All Night
Two songwriters responsible for a few top hits in the ’80s including Cyndi Lauper’s ‘True Colors’ and Madonna’s ‘Like a Virgin’ wrote ‘I Drove All Night’ for Roy Orbison, though they never dreamed he would record it. Tom Kelly and Billy Steinberg grew up listening to Orbison and were huge fans. By the time the late ’80s rolled around, Roy wasn’t in the spotlight anymore. Instead, he was playing smaller supper clubs around California for his bread-and-butter audience, middle-aged women. Though Kelly and Steinberg attended one of his supper club shows and chatted with Roy’s manager, nothing came of it. Several months later though, they all happened to be recording at the same studio at the same time, and before they knew it, Roy was laying down vocals to their song. He wasn’t signed to a major label at the time, and he passed away before he could finish work on his latest album. But when Orbison’s estate began releasing new works posthumously, ‘I Drove All Night’ ended up on the ’92 album, King of Hearts. For a fun trip back in time, check out the music video. A very young Jason Priestley of hit show 90210 and Jennifer Connelly (most recently Top Gun: Maverick) play two star-crossed lovers.
5. Only the Lonely
“Only the lonely know the way I feel tonight.” This iconic lyric is perhaps Roy’s most famous line he ever sang. Even at his smaller shows later in his career, audiences sang ‘Only The Lonely’ as loud as they could. A deeply emotional song about heartbreak, it’s one of his signature tracks. It was an early collaboration with fellow longtime songwriting partner Joe Melson, who began working on the tune when he was still a teenager and got his heart broken by a girlfriend. A huge hit in both the UK and the US, it’s arguably his most famous song. The writing duo originally offered it to both The Everley Brothers and Elvis because Orbison had no intention of singing it. But once The Everley Brothers heard it, they persuaded him to record it because it was perfect for his vocal range and style.
4. In Dreams
Playing a pivotal part in the ’80s psychological noir film Blue Velvet, the movie became an instant cult classic and Orbison’s song ‘In Dreams’ can be heard in one of the film’s most iconic scenes. In fact, fans of Blue Velvet agree the song is really what makes the scene so magnificent. Actor Dean Stockwell is featured in the sequence, who is responsible for the film’s otherworldly psycho-antagonist role. It’s known as one of cinematography’s “weirdest” scenes, and Stockwell’s performance as he lipsyncs to Orbison’s ‘In Dreams’ immediately catapults you to a place outside of physical reality. At first, Orbison was not pleased that director David Lynch used his song in the film due to the illicit activities featured throughout the plot. However, after viewing the scene and familiarizing himself with the inner workings of the story, he came to appreciate how the song transported the film’s scene to a more multi-dimensional level.
3. You Got It
Another commercial success for Orbison in the ’80s, ‘You Got It’ was included on his comeback album Mystery Girl, which helped launch a new era of his music, despite the project debuting mere months after his sudden death from a heart attack. Tom Petty helped write the single and even played guitar and sang backup on the original recording. The tune’s open, major chord structure and uplifting melody made it a popular track, and it was used in several pop culture pieces. The most well-known version appears in the ’95 film Boys On The Side. Both Whoopi Goldberg and Bonnie Raitt covered the track for the comedy-drama. Raitt’s version put the song back in the top 40 on the charts.
2. Oh, Pretty Woman
A hit that rivals the success of ‘Only the Lonely,’ Orbison worked with another songwriting friend of his, Bill Dees, on this driving yet playful pop tune. Released in ’64, it became a number one hit both in the states and internationally, and experienced a resurgence in the ’90s when it became the theme song to the hit film Pretty Woman starring Richard Gere and Julia Roberts. The two songwriters were at Roy’s house trying to come up with new material when his wife Claudette mentioned she was going to the store. When Roy asked if she needed any cash, Dees quipped, “Pretty woman never needs any money.” Dees’ perfectly-timed comeback was the catalyst for ‘Oh, Pretty Woman.’ The song was the fastest they’d ever put out. The single was released less than a month after the pair wrote it, and they got it recorded in one day. Not only is the chart-topping single an iconic Orbison track, but its popularity in the ’90s gave it new life, making it an American pop classic for younger generations.
1. Crying
Orbison gives the performance of a lifetime with his hit ‘Crying.’ Released in 1961, he went against social conventions of the time and put out a tear-jerker of a ballad while other male acts focused on songs in the wheelhouse of early rock and roll, dealing with wild women and good times. Written after a chance encounter with a former flame made him realize it was too late to get her back, even live versions of the single are performed flawlessly. Orbison’s vocal performance not only features him seamlessly gliding through his full range, from falsetto notes to full voice, but towards the end of the song his vocal melody gives the effortless impression he’s actually crying. Only Roy could pull off this technique without it coming off as cheesy. Elvis spoke words of truth when he said in an interview that Orbison had “the most perfect voice,” and was “the greatest singer in the world.” That’s quite a compliment coming from “The King” of rock and roll. We’d have to agree.
