Curless was born in Fort Fairfield, Maine, United States, and moved with his family to Massachusetts at the age of eight.

[1] He began his music career in 1948 in Ware, Massachusetts, where he hosted a radio show and toured with a local band called the Trail Blazers.

[1] In 1957, Curless returned to the public spotlight and appeared on the CBS television show Arthur Godfrey's Talent Scouts.

[1] He spent much of the late 1950s performing in clubs in California and Las Vegas but occasionally returned home to Maine to recover from periods of illness and fatigue.

[1] In 1965, Curless recorded one of the biggest hits of his career, "A Tombstone Every Mile", which cracked the top 5 on the Billboard country charts and propelled him to national fame.