The Teen Kings went to Memphis. Roy had grown very tired of playing and singing, Ooby Dooby, but Phillips wanted to record the song again in a better studio. Roy became a bit unhappy with Phillips' control over the band and the recording session. He told Roy how to sing the song, even though Roy and the band had performed it countless time. However, when the record was released, it broke into the Billboard Hot 100, settling at number 59 and selling 200,000 copies. The Teen Kings toured with Sonny James, Johnny Horton and Johnny Cash after the release of the record.

With only one charted song, the Teen Kings began to write more songs, such as Go! Go! Go! and Rockhouse. However, during rehearsal at Sun Records one day, the band broke up over credits and royalties. After the breakup, Roy wrote a ballad called, The Clown. Upon hearing it, Sun Records producer, Jack Clement, told Roy that he'd never make it as a ballad singer!

Though Roy had only moderate success at Sun Records, he did find himself in Elvis Presley's social circle, along with others who were gaining fame.

In 1957, he married his girlfriend, Claudette Frady. He wrote a song for her, called Claudette, which was recorded by the Everly Brothers and went to the top ten. From the royalties he earned at Sun, he made a down payment on a new Cadillac.

In time, he became very frustrated at Sun and quit recording to return to Texas, where he toured the music circuit. In 1958, he quit performing altogether for a period of about seven months. This was the year that his first son, Roy Jr. was born. His new Cadillac was repossessed and he found himself in dire straits, relying on the generosity of friends and family members to survive. It seemed that his dream had ended before it was allowed to start.

In the late 1950s, for only a brief time, Roy wrote songs for Acuff-Rose in Nashville. He would write a song, make several demo tapes and send it to Wesley Rose, who would then attempt to find an artist interested in it. RCA invited him to record a song called Seems to Me, written by Boudleaux Bryant. RCA was not impressed and didn't allow Roy to record any more songs.

Wesley Rose then directed Roy to Fred Foster at Monument Records. It was at Monument that Roy began to experience the success he had hoped for. Initially, he recorded Paper Boy and Pretty One, neither of which had any gainful effects. He recorded Uptown, which reached only 72 on the Billboard Charts.

This was at a time that Rock N Roll was still in its infancy, but it was experiencing devastating events. Elvis had been drafted into the army. Buddy Holly died in a plane crash in Clear Lake, Iowa and Eddie Cochran was killed in an auto accident in the UK. Little Richard became involved in the church and backed out of Rock N Roll. Jerry Lee Lewis lost his popularity when he married his 13-year-old cousin. It appeared that Rock N Roll had stagnated into a clean version of pop music, unlike its more raw beginnings.

Roy studied the top forty until he developed a feel for what was well liked. Roy and Joe Melson wrote a song in April of 1960, called Only the Lonely. They tried to sell it to Elvis, who turned it down. They tried to sell it to the Everly Brothers, who also turned it down. So, Roy decided to record it himself. The Anita Kerr singers backed him up on the recording and in the song, he hit an incredibly high note in falsetto that clearly showed a voice with extreme range! Only the Lonely quickly climbed the charts, garnering a no. 2 slot in the U.S. and a number 1 slot in the U.K. For fifteen weeks, it enjoyed success on the U.S. charts.