Roy left Sun in 1957 and signed to music publishers Acuff-Rose, convinced his true calling was as a songwriter. Indeed, his song "Claudette", written while at Sun, was a Top Thirty hit for The Everly Brothers in 1958. A brief stint with RCA followed but neither of the Chet Atkins produced singles he recorded met with much success. Nonetheless, Roy's star was soon to be in the ascendant following a conversation between his manager Wesley Rose and a former Mercury promotion man, Fred Foster. Foster had heard a record by Warren Smith on Sun called "Rock and Roll Ruby". "Fred thought I'd recorded that and so he signed me, thinking I was someone else!", said Roy. Orbison, nonetheless, found his niche with Foster's newly formed label, Monument, beginning with the 1960, #94 hit "Up Town", one of the very first Nashville sessions to incorporate strings as opposed to fiddles. "Foster was smart enough to get out of the way at the right time. He didn't say 'sound like this' or 'play it this way.' He just knew what sounded good to him. Which is the best producer you can have. Whatever sounds beautiful to the producer is fantastic," Roy remembered.
On a songwriting level, Orbison began collaborating with fellow Texan Joe Melson. Beginning with "Up Town", the pair had a long and extremely productive writing partnership. Of Roy's first fifteen Billboard Top 40 hits, six were penned by the Orbison / Melsom team. They included the breakthrough record, "Only The Lonely", a pure gold fusion of R&B and country which narrowly missed out on hitting number one in America in the Summer of 1960. In Britain, however, it didn't just top the charts, but remained in the Top 40 for nearly six months. "Only The Lonely" is of course the song regarded by many as the starting point of Roy's classic ballad sound. Most of the hits that would follow, such as "Blue Angel" (#9), "Running Scared" (#1), "Crying" (#2), "Dream Baby" (#4), "In Dreams" (#7) and "It's Over" (#9), contained a vivid combination of hurtful romantic longing, combined with near-operatic vocals that established Roy as a truly unique talent. But as Orbison would stress repeatedly, his hits were by no means a catalogue of sad songs or romantic tragedy. "On balance, I'd say it was at least fifty-fifty. "Dream Baby", "Mean Woman Blues", "Running Scared", even "Pretty Woman" has a happy ending!"
Roy's trademark look came about the night he misplaced his regular glasses and had to rely on a pair of prescription sun-glasses. His management liked the mysterious look it gave him, and soon they were the only ones he wore. Eight Top Ten hits in the four years between 1960 and 1964 paved the way for the biggest selling record of his career, "Oh, Pretty Woman". Estimated to have sold over 7 million copies in 1964 alone, it topped the American charts for three weeks, holding at bay the British invasion by bands such as The Animals and Manfred Mann. In Britain, it gave Roy his second straight Number One (It's Over had dominated the UK charts in the spring of '64) and, like its predecessor, remained on the chart for over four months. While he was the only American vocalist to ride out the British invasion, Orbison also toured Britain regularly, initially sharing a bill with The Beatles, who, at that time were unknowns in America. "I messed up the first day I got there. I walked out in this little theatre and they had Beatles placards everywhere, life-size ones. And I said, 'What's all this? What is a Beatle anyway?' and John Lennon said, 'I'm one'. He was standing right behind me". The Beatles, of course, were hugely influenced by Orbison and their slow-tempo version of "Please Please Me" was very much a tribute to him.
In 1965, Orbison signed to MGM, lured by a lucrative deal that also offered the potential of Presley-level movie stardom. Indeed, he did star in 1968's The Fastest Guitar Alive, but MGM were getting in to financial trouble and Orbison's rich vein of hits began to dry up. To compound this, Roy's private life was marred when, in the midst of reconciliation with his ex-wife, Claudette, she was killed in a motorcycle accident. Two years later in 1968, two of Roy's sons were killed in a house fire. Reduced to touring clubs, Roy returned to his Country roots and recorded for Mercury and Asylum in the '70s.
His reputation as an influential master, however, began to soar once again via covers of his earlier work. Linda Ronstadt set the ball rolling with "Blue Bayou" (#3 in 1977) and three years later, Roy won a Grammy for his duet with Emmylou Harris for "That Loving You Feeling again". A year later, Don McLean scored with "Crying" (#5), but real success came Roy's way again when his re-recording of the 1963 hit "In Dreams" became a pivotal element of David Lynch's 1986 movie, Blue Velvet. Signing to Virgin, and with all of his old original recordings embroiled in bankruptcy proceedings, Orbison set about re-recording his songs "Just so's they would be available," and released a double-set called "In Dreams".
In 1987, Roy was inducted in to The Rock And Roll Hall Of Fame and within twelve months had become a member of The Travelling Wilburys alongside Tom Petty, Bob Dylan and George Harrison. With his career rejuvenated, Orbison fronted the extraordinary TV special recorded at the Coconut Grove in Los Angeles, Roy Orbison and Friends: a Black and White Night. Roy's friends who became his backing band were indeed stellar; Bruce Springsteen, Tom Waits, k d lang, Elvis Costello, T Bone Burnett, Jackson Browne, Bonnie Raitt, J.D. Souther, Jennifer Warnes and more. Roy also hit the charts again with a duet along side k d Lang and their cover version of Roy's classic, "Crying", which peaked at #42 on the Hot Country singles chart, though it was a more substantial hit in the UK in 1992 when it reached #13.
Just as his second wind as a recording star kicked into high gear, tragedy struck again. Roy returned to his home in Hendersonville, Tennessee to rest before flying to England to film more videos for The Traveling Wilburys. On December 6th, 1988, he spent the day flying model airplanes with his sons and ate dinner at his mother's home. Later that day, he suffered a fatal a heart attack at the age of 52. Among the multitude of artists he had influenced that paid tribute, U2's Bono summed up many feelings when he said, "Writing for him was like writing for Elvis, who was the only comparable vocal talent. His great gift was to turn the pain and bad luck that he experienced into ground breaking songs". Bono had written "She's a Mystery To Me" especially for Roy. Released after his death, it gave Orbison his last Top 30 hit in Britain. Paul McCartney simply said, "He was and always will be one of the greats of Rock 'n' Roll." Posthumously released in 1989, Roy's "Mystery Girl" album became the biggest selling record of his career. That success was sparked by another Billboard Top Ten single, "You Got It", written by fellow Wilburys Tom Petty and Jeff Lynne. In 1992, Virgin released "King Of Hearts", a collection of previously un-issued songs. "The Very Best of Roy Orbison", documenting his career from its beginning through the last years of his life, was released by Virgin Records in November 1996.
Even in death, Roy Orbison's talent has never shone brighter. He remains as one of Rock's truly legendary figures, a consistent talent whose influence grows with each passing year. His was a combination of voice and songs that, harnessed together, unleash a rare power which grabs listeners by the heart and holds them forever enthralled. Orbison's was a special talent no better acknowledged than by Bruce Springsteen when inducting Roy into the Rock And Roll Hall Of Fame in 1987. "In 1975, when I went in to the studio to make "Born To Run", I wanted to make a record with words like Bob Dylan that sounded like Phil Spector. But, most of all, I wanted to sing like Roy Orbison." In 2002, Billboard magazine listed Orbison at number 74 in their top recording artists of all time. He received a posthumous star on the Hollywood Walk Of Fame in 2010. In November, 2015, a so-called "lost album" of twelve tracks called "One Of The Lonely Ones" was included in an eleven album Orbison box set called "The MGM Years". The songs were recorded in the mid-1960s, but had been kept in the company's vaults until this release.