The third single for Fred Foster's Monument label was "Only the Lonely", which became the first song that truly probed the frightening potential of Roy Orbison's voice, and established his uniqueness. The song peaked at number 2 on the Billboard Charts and became number 1 in the UK.

The challenge to consolidate "Only the Lonely" was a difficult one. The follow-ups, "Blue Angel" and "I'm Hurtin", were something special.

That next magical success was "Running Scared", and it climbed all the way up to number 1 in the USA.

A few things contributed to Roy Orbison's success. The songs, the production, and the performance were key factors. The songs were completely original in structure, sound and style. Totally innovative compositions, that didn't exist until then. It became a style. Fred Foster really went for quality instead of quantity. He was willing to splash money on a session without any guarantee of payback. He was also willing to take a chance on a sound that did not conform to accepted market norms.

After that came "Crying", "Candy Man", "Dream Baby", "Working for the Man", "Leah", "In Dreams", "Pretty Paper", "Blue Bayou", "Mean Woman Blues ", "It's Over". This became an unbroken string of Top 40 hits that lasted for four years. Roy became the top selling American artist and one of the world's biggest names .

In May 1963, and with the success of "In Dreams", Wesley Rose eventually accepted an invitation for Roy to tour England on a bill with The Beatles, who meant nothing in the United States at that time. The tour was sold-out in one afternoon. On the first night, Roy did fourteen encores before The Beatles could get on stage.

Roy Orbison was one of the few hit-makers to hold his ground, and even to increase his popularity in the wake of the so-called British Invasion. He did it by maintaining a matchless quality of releases, with an original variety of content, structure, tempo and rhythm. He was also an extremely subtle song craftsman, making changes during the course of a session, or between sessions, adding the final commercial gloss to a song.

"Oh Pretty Woman" was recorded on August 1st, 1964. It was written by Roy together with his new writing partner Bill Dees and it became Roy's biggest hit, and in fact the most popular song of all time. Released in August in the US and in September in the UK, it went to number one in every country of the World. By most estimates, the song sold about seven million copies that same year.

Orbison toured Australia with opening acts such as the Beach Boys in 1964 and with the Rolling Stones 1965. Roy also toured extensively in Europe and Asia.

Several major record companies showed interest in Orbison after his tenure with Monument. MGM made and offer of 1,000,000 dollars. The first single, "Ride Away", was a success, but it would be the biggest single in the US that Roy would have for over 10 years. What seemed to be just a change of record labels became a huge turn in Roy's career. A dark period ensued as Orbison's private life began to unravel as well. In 1966, his wife Claudette, who he married in 1957, was killed in a motorcycle accident. Matters turned worse two years later when two of his three children died when his Hendersonville house burned down (Roy sold the lot to his best friend Johnny Cash. Cash's home at the exact same location would also later burn to the ground.) Roy found himself unable to write songs for a while, but maintained a positive outlook and continued touring. In late 1966 Roy started filming "The Fastest Guitar Alive", the movie in which he starred.

MGM was very successful at that time, but that was about to change due to troubles with MGM's Motion Picture Studios. Roy's success practically made Monument Records, but at MGM he was just one more superstar among MGM's roster. Quantity was chosen over quality and he was required to release certain amount of singles and albums per year, which took it's toll.

Roy met a German girl by the name of Barbara Anne Marie Wilhonnen Jacobs in August 1968, in Leeds, England. She moved to the USA in late 1968 and they were married in Nashville on May 25, 1969, and start building a brand new house just one block away from where Roy's old house used to stand on Old Hickory Lake in Hendersonville, Tennessee.