Hamilton had been a member of the Opry since 1960, though his music career dates back further and crosses genre lines. Before focusing on country music, had a smash hit with the teen-pop ditty "A Rose and a Baby Ruth," a million-selling song (written by John D. Loudermilk) that reached the top 10 on Billboard's Hot 100 in 1956.

However, during a trip to the Ryman Auditorium in Nashville to watch the Grand Ole Opry in 1960, he decided to switch from pop to country. He's considered to be the first artist to have made that transition (Conway Twitty made a similar move from pop to country, but his first true country record wasn't released until 1965).