In 1953, Cupp and his family moved to Texarkana where he enrolled at Arkansas High School and teamed up with Elvis Presley-sound-alike Cheesie Nelson to form a locally popular country duo.
[3] In May 1956, Cupp and the Flying Saucers recorded "Do Me No Wrong" and "Baby Come Back" at KWKH Radio in Shreveport, Louisiana.
[4] Frustrated with the change of his style and backing band, Cupp joined the U.S. Air Force in 1957 to avoid further commitments outlined on his recording contract.
After being honorably discharged in 1961, performing became a hobby for Cupp as he started a career as a technical engineer and married his high school sweetheart, Loretta Gaye Michael.
[3] Cupp formed a jazz band called the Variables that released one single, "After All", in 1967 on the independent record label, Chance.