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The Teen Kings went to Memphis and although Orbison had grown weary of "Ooby Dooby", Phillips wanted to cut the record again in a better studio. Orbison rankled quietly at Phillips' dictating what the band would play and how Orbison was to sing it. However, with Phillips' production, the record broke into the Billboard Hot 100, peaking at No. 59 and selling 200,000 copies. The Teen Kings toured with Sonny James, Johnny Horton, and Cash. Much influenced by Elvis Presley, Orbison performed frenetically, doing "everything we could to get applause because we had only one hit record". The Teen Kings also began writing more material such as "Go! Go! Go!" and "Rockhouse", generally in standard rockabilly style. The band ultimately split over disputed writing credits and royalties, but Orbison stayed in Memphis and asked his 16-year-old girlfriend, Claudette Frady, to join him. They stayed in Phillips' home, where they slept in separate rooms; in the studio Orbison concentrated on the mechanics of recording. Sam Phillips remembered being much more impressed with Orbison's mastery of the guitar than his voice; a ballad Orbison wrote called "The Clown" was met with lukewarm appreciation at best. Sun Records producer Jack Clement told Orbison after hearing it that he would never make it as a ballad singer.

He found a modicum of success at Sun Records and found his way into Elvis Presley's social circle, once going to pick up a date for Presley in his purple Cadillac. Orbison sold "Claudette", a song he wrote about Frady — whom he married in 1957— to The Everly Brothers and it appeared on the B side of their smash hit "All I Have To Do Is Dream". The first and perhaps only royalties Orbison earned from Sun Records enabled him to make a down-payment on his own Cadillac. However, frustrated at Sun, Orbison gradually stopped recording, toured music circuits around Texas to make a living, and for seven months in 1958 quit performing completely. His car repossessed and in dire financial straits, he often depended on family and friends for funds.

For a brief period in the late 1950s Orbison made his living at Acuff-Rose, a songwriting firm concentrating mainly on country music. After spending an entire day writing a song, he would make several demo tapes at a time and send them to Wesley Rose, who would try to find the musical acts to record them. Orbison attempted to sell songs he recorded that were written by other writers to RCA Victor as well, working with and being completely in awe of Chet Atkins, who had played guitar with Presley. Orbison tried one song penned by Boudleaux Bryant called "Seems to Me". Bryant's impression of Orbison was "a timid, shy kid who seemed to be rather befuddled by the whole music scene. I remember the way he sang then — softly, prettily but almost bashfully, as if someone might be disturbed by his efforts and reprimand him." After two tepid attempts with RCA Victor, they decided not to option Orbison for another song. Wesley Rose maneuvered Orbison into the sights of producer Fred Foster at Monument Records.

Arrival: 1960–1964

In his first sessions at Monument in Nashville, Orbison took on a song that RCA refused, "Paper Boy", and wrote another, "Pretty One". Playing shows late into the night, and living with his wife and young child in his tiny apartment, he often sought refuge by taking his guitar to his car and writing songs there. Songwriter Joe Melson, who had a passing acquaintance with Orbison, tapped on his car window one day in Texas in 1959 and the two decided to try to write some songs together. They experimented with the doo-wop backup singers arranged by Anita Kerr in a song called "Uptown"; Orbison was allowed to use strings on the record, which he enjoyed. Melson later recalled, "We stood in the studio, listening to the playbacks and thought it was the most beautiful sound in the world". The song earned a modest spot at No. 72 on the Billboard Top 100 and Orbison set his goal on negotiating a contract with an upscale nightclub somewhere. Rock and Roll itself, in its infancy in the late 1950s, was stalled. Elvis Presley was in the Army. Eddie Cochran and fellow Texan Buddy Holly — both of whom Orbison had previously toured with — had died, to Orbison's deep astonishment. Little Richard found religion and Chuck Berry had been arrested and spent time in jail. Orbison's former Sun Records colleague Jerry Lee Lewis was disgraced when his marriage to his 13-year-old cousin was reported widely in the press. In their wake, pop music filled the radio waves, dominated by teen idol crooners who sang cleansed formulas like those about The Twist dance craze and "death discs" like "Teen Angel" and "Endless Sleep".

 Writing for the voice

Influenced by contemporaneous hits such as "Come Back to Me My Love" and "Come Softly to Me", Orbison and Melson wrote a song in April 1960 which, when recorded, employed strings, the Anita Kerr doo-wop backup singers, and finally, an astounding note hit by Orbison in falsetto that showcased a powerful voice which, according to biographer Clayson, "came not from his throat but deeper within". It was titled "Only the Lonely", and Orbison and Melson tried to pitch it to Elvis Presley and the Everly Brothers, both of whom turned it down. Orbison released his own version instead and it shot to No. 2 on the Hot 100 in the U.S. and hit No. 1 in the UK and Australia. According to Orbison, the subsequent songs he wrote with Melson during this period were constructed with his voice in mind, specifically to showcase its range and power. He told Rolling Stone in 1988: "I liked the sound of [my voice]. I liked making it sing, making the voice ring, and I just kept doing it. And I think that somewhere between the time of 'Ooby Dooby' and 'Only the Lonely', it kind of turned into a good voice."

Instantly Orbison was in high demand. He appeared on American Bandstand and toured the U.S. for three months non-stop with Patsy Cline. When Presley heard "Only the Lonely" for the first time, he bought a box of copies to pass to his friends. Melson and Orbison followed it with the more complex "Blue Angel" which peaked at No. 9, a self-performed version of "Claudette", and "I'm Hurtin'", which rose to No. 27.

Orbison was now able to move his wife and son to Nashville full-time. Back in the studio, seeking a change from the doo-wop styled pop sound of "Only the Lonely" and "I'm Hurtin'", Orbison worked on a new song, "Running Scared", based loosely on the rhythm of Ravel's Boléro; the song was about a man on the run with a woman, followed by another man who is trying to take her away. Orbison encountered a difficulty when he found himself unable to hit the song's highest note without his voice breaking. He was backed by an orchestra in the studio and the sound engineer told him he would have to sing louder than his accompaniment because the orchestra was unable to be softer than his voice.Fred Foster then put Orbison in the corner of the studio and surrounded him with coat racks in an improvised isolation booth to emphasize his voice. Orbison was unhappy with the first two takes, but in the third, he abandoned the idea of using falsetto and, to the astonishment of everyone present, sang the final high G sharp naturally. On that third take, "Running Scared" was completed. Fred Foster later recalled, "He did it, and everybody looked around in amazement. Nobody had heard anything like it before."

Developing the Just weeks later "Running Scared" reached No. 1 on the Hot 100 chart. The composition of Orbison's following hits reflected "Running Scared": a story about an emotionally vulnerable man facing loss or grief, culminating with a surprise ending in a crescendo that employed Orbison's dynamic voice. "Crying" followed in July 1961 and reached No. 2; it was coupled with an R&B up-tempo song titled "Candy Man" written by Fred Neil, that stayed on the charts for two months. Orbison's second son was born in 1962, and Orbison hit No. 4 in the U.S. and No. 2 in the UK with "Dream Baby", an upbeat song written by veteran country songwriter Cindy Walker. The rest of the year he charted with "The Crowd", "Leah", and "Workin' For the Man", which he wrote about working one summer in the oil fields near Wink. His relationship with Joe Melson, however, was deteriorating over Melson's growing concerns that his own solo career would never get off the ground.

Lacking the photogenic looks of many of his rock and roll contemporaries, Orbison eventually developed a persona that did not reflect his personality. He had no publicist in the early 1960s, no presence in fan magazines, and his single sleeves did not feature his picture. Life magazine called him an "anonymous celebrity". After leaving his thick eyeglasses on an airplane in 1962 or 1963, Orbison was forced to wear his Ray-Ban Wayfarer prescription sunglasses on stage and found that he preferred them. His biographers suggest that although he had a good sense of humor and was never morose, Orbison was very shy and suffered from severe stage fright; wearing sunglasses helped him hide somewhat from the attention. The black clothes and desperation in his songs led to an aura of mystery and introversion. Years later, Orbison said "I wasn't trying to be weird, you know? I didn't have a manager who told me to dress or how to present myself or anything. But the image developed of a man of mystery and a quiet man in black somewhat of a recluse, although I never was, really."

His dark and brooding persona, combined with his tremulous voice in lovelorn ballads marketed to teenagers, helped Orbison corner the pop market in the early 1960s. He had a string of hits in 1963 with "In Dreams" (No. 7 in the U.S.), "Falling", "Mean Woman Blues" (No. 5 in the U.S.), and "Blue Bayou", all of which also hit the Top 10 in the UK. He finished the year with a Christmas song written by Willie Nelson titled "Pretty Paper".

As "In Dreams" was released in April 1963, Orbison was asked to replace guitarist Duane Eddy on a tour of the UK in top billing, with a local band that was becoming massively popular named The Beatles. When he arrived in England, however, he saw the amount of advertising devoted to the quartet and realized he was no longer the main draw. He had never heard of them and, annoyed, asked hypothetically, "What's a Beatle anyway?" to which John Lennon replied after tapping his shoulder, "I am." On opening night, Orbison opted to go onstage first although he was the more established act. Known for having raucous shows expressing an extraordinary amount of energy, Lennon, Paul McCartney, George Harrison, and Ringo Starr stood dumbfounded backstage as Orbison performed completely still and simply sang through fourteen encores. Finally, when the audience began chanting "We want Roy!" again, Lennon and McCartney prevented Orbison from going on again by physically holding him back. Starr later said, "In Glasgow, we were all backstage listening to the tremendous applause he was getting. He was just standing there, not moving or anything." Through the tour, however, both acts quickly learned to get along, a process made easier by the fact that the Beatles admired his work. Orbison felt a kinship with Lennon, but it was Harrison with whom he would later form a strong friendship. The moniker of "The Big O" would eventually follow him back to the States, where it became an unofficial nickname for Orbison.

Orbison recorded in the 1970s, but his albums performed so poorly that he began to doubt his talents. Author Peter Lehman would later observe his absence was a part of the mystery of his persona: "Since it was never clear where he had come from, no one seemed to pay much mind to where he had gone; he was just gone." His influence was apparent, however, as several artists released covers of his songs that performed very well. "Love Hurts" was remade by Gram Parsons and Emmylou Harris, and again by heavy metal band Nazareth. Sonny James sent "Only the Lonely" to No. 1 on the country music charts. Bruce Springsteen ended his concerts with Orbison songs and Glen Campbell had a minor hit with a remake of "Dream Baby". A compilation LP of Orbison's greatest hits went to No. 1 in the UK in 1977. The same year he began to open concerts for The Eagles, who started as Linda Ronstadt's backup band. Ronstadt herself covered "Blue Bayou" in 1977, her cover reaching No. 3 on the Billboard charts and remaining in the charts for 24 weeks. Orbison credited this cover in particular for reviving his memory in the popular mind, if not his career.