The Teen Kings has been played on NTS in shows including Diddy Wah, featured first on 18 May 2015. Songs played include Go! Go! Go! and Ooby Dooby.

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 number 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's 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 to RCA Victor songs he recorded that were written by other writers 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 of "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."

Playing shows late into the night, and living with his wife and young child in his tiny apartment, Orbison often sought refuge by taking his guitar to his car and writing songs there. Songwriter Joe Melson, an acquaintance of Orbison's, tapped on his car window one day in Texas in 1958 and the two decided to try to write some songs together. During three recording sessions in 1958 and 1959, Orbison and Melson recorded seven songs at RCA Nashville, with Atkins producing, but only two songs were judged worthy of release by RCA; Wesley Rose maneuvered Orbison into the sights of producer Fred Foster at Monument Records.