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Six definitive songs: The ultimate beginner's guide to Roy Orbison

The simple response to the question of Roy Orbison’s impact would be his aptly named title, ‘The Soul of Rock and Roll’. Through a short but incredibly memorable string of hits in the ’60s, he collected lifelong fans and inspired soon-to-be rock legends with his unique musicianship. So, to honour arguably the most unique singer/songwriter in the history of popular music, we’ve provided the ultimate beginner’s guide to Roy Orbison.

Orbison’s love for music began as early as age six when his father bought him a guitar. By 1949, now age thirteen, he’d formed his first band called The Wink Westerners. The band morphed into The Teen Kings, which eventually ended, prompting Orbison to begin his solo career, a decision that would allow him to fully come into his full potential as an artist. 

His passionate vocals, complex song compositions, and moody ballads quickly catapulted him to legendary status, earning him the nicknames ‘the Caruso of Rock’ and ‘the Big O’. While most of his contemporaries were projecting an air of heavy masculinity, Orbison chose to play and sing straight from the heart. Even his signature look developed from a vulnerable state—the dark glasses came from a major case of stage fright. 

Today, Orbison’s legacy lives on with honours, including an induction into the Rock and Roll Hall of Fame and Nashville Songwriters Hall of Fame, a Grammy Lifetime Achievement Award, and five other Grammy Awards. 

Although it’s impossible to confine his incredible discography, here are the six definitive songs that best showcase Roy Orbison’s tremendously impactful career. 

Roy Orbison’s six definitive songs: 

‘Ooby Dooby’ (1956)

Written by two of Orbison’s college buddies Wade Lee Moore and Dick Penner, Orbinson’s early band The Wink Westerners recorded a demo of ‘Ooby Dooby’ for country music talent agent and record producer Jim Beck’s studio in Dallas, Texas. Although Orbison thought the band had a sure shot as being signed to Columbia Records after a successful recording, it never happened, leaving the group discouraged. 

After rebranding The Wink Westerners as The Teen Kings in 1956, the group recorded ‘Ooby Dooby’ in Sam Philips’ Sun Records studio in Memphis, Tennessee. The song quickly catapulted into the Top 60, but the follow-up singles did not chart. The Teen Kings split up in December 1956, a move that prompted Orbison to begin his solo career. 

‘Only the Lonely (Know The Way I Feel)’ (1960)

Written with his frequent songwriting partner Joe Melson, Orbison initially intended to give this song away. He offered it to Elvis Presley and the Everly Brothers, but the latter thought he should record the song himself. In May of 1960, Orbison released the song as a 45 rpm single on Monument Records in May of 1960, and it went straight to number two on the US Billboard pop music charts and reached number one in the UK.

Although Orbison’s image tended to be synonymous with his moody discography, especially in tunes like ‘Only the Lonely,’ he later explained to NME that many of his most painful songs were written in happier times. “I’ve always been very content when I wrote all those songs. By this, I’m saying that a lot of people think you have to live through something before you can write it, and that’s true in some cases, but I remember the times that I was unhappy or discontent, and I couldn’t eat, I couldn’t sleep, I couldn’t communicate, and I certainly couldn’t write a song, no way. All the songs I wrote that were successful were written when I was in a contented state of mind.”

‘Crying’ (1961)

‘Crying,’ a song now remembered for its vulnerable tone and universality, came about from regret Orbison faced from a past relationship. In a later interview, Orbison explained about the inspiration, “I was dating a girl, and we broke up. I went to the barbershop to get a haircut and I looked across the street, and there was this girl that I had split up with. I wanted to go over and say, ‘Let’s forget about what happened and carry on.’ But I was stubborn.

“So I got in the car and drove down the street about two blocks and said to myself, ‘Boy, you really made a mistake. You didn’t play that right at all.’ It certainly brought tears to my eyes, and that’s how I came up with ‘Crying.'”

The song was released in 1961 and became a number two hit in the US for Orbison, proving that it was possible to follow up a hit ballad with another hit ballad — an unconventional move at the time. The track continued to inspire throughout the years and even experienced a resurgence in 1980 when singer/songwriter Don McLean’s rendition rose to number one in the UK charts.

‘In Dreams’ (1963)

Orbison claimed that many of his songs came to him while he was sleeping, which he later revealed was also the case for the 1963 release ‘In Dreams’. He attributed this way of conjuring inspiration to the fact he often listened to music while asleep. Orbison was only half-asleep, though when the sudden inspiration for the song hit him and thought, “Boy, that’s good. I need to finish that. Too bad things don’t happen in my dreams.” He fell back asleep and, by the next morning, wrote the entire song in 20 minutes.

‘In Dreams’ was recorded at the RCA Studio B in Nashville on January 4, 1963, and released later the same month. It’s yet another example of Orbison’s ethereal songwriting chops.

‘Oh, Pretty Woman’ (1964) 

In 1964, while writing with his songwriting partner Bill Dees, Orbison told him to play anything that came to mind. When Orbison’s wife Claudette announced she was going into town to do some shipping, Orbison asked if she needed any money. Dees joked, “Pretty woman never needs any money.” This line inspired Orbison to start riffing and immediately came up with, “Pretty woman walking down the street.” 

Bill Dees recalled in a later interview, “He [Orbison] sang it while I was banging my hand down on the table, and by the time she returned, we had the song,” he shared. “I love the song. From the moment that the rhythm started, I could hear the heels clicking on the pavement, click, click, the pretty woman walking down the street in a yellow skirt and red shoes. We wrote ‘Oh Pretty Woman’ on a Friday, the next Friday we recorded it, and the next Friday, it was out. It was the fastest thing I ever saw. Actually, the yeah, yeah, yeah in ‘Oh Pretty Woman’ probably came from The Beatles.”

Released in August of 1964, ‘Oh, Pretty Woman’ became Orbison’s last big hit, selling seven million copies and being certified gold by the RIAA within months of its initial release.

‘You Got It’ (1989)

After Orbison’s wildly successful string of hits in the ’60s, his career began to dwindle when the ’70s came around. In the ’80s, he experienced a resurgence in popularity as celebrated musicians were coming out with the support of Orbison, stating his influence on them. These musicians included George Harrison, Tom Petty, Jeff Lynne, and Bob Dylan, who, with Orbison’s help, created the supergroup the Traveling Wilburys. After the group’s debut album release in 1988, his fellow band members helped him create a solo comeback album Mystery Girl, which included the first single, ‘You Got It.’

Written in the winter of 1987 with Jeff Lynne and Tom Petty, the trio recorded the song in April of 1988 in a makeshift setup in Mike Campbell’s garage in Los Angeles, California. Lynne, Petty, and Phil Jones provided other instrumentation and background vocals. The only public performance of the song was at the Diamond Awards Festival in Antwerp, Belgium on November 19, 1988. Less than a month later, on December 6, 1988, Orbison suddenly died of a heart attack, forcing the album and song to be released posthumously. It remains an unforgettable piece.