Bob Neal offered Roy a spot on an Everly Brothers show in Hammond, Indiana in March 1958. The Everlys needed a song for their new single and they asked Roy if he had anything. He sang his new composition "Claudette" and they asked him to write the words down. So he did, on the top of a shoebox. Later, Wesley Rose, from Acuff-Rose Music Publishing in Nashville, signed Roy with his Nashville publishing company. He also gave Roy a contract with RCA Victor where he briefly worked with Chet Atkins.

The Everly's "Claudette" was released on late March 1958 as the B-side of "All I Have To Do Is Dream". The A side went to number 1; "Claudette" peaked at Number 30. At this point, his songs were also recorded by Buddy Holly, Jerry Lee Lewis and Rick Nelson.

Wesley Rose rapidly got Roy another contract with the new independent Monument Records when his RCA deal ran out in Mid-1959.