Randy and his brother Ricky were encouraged to pursue their musical talents by their father, who was a fan of Hank Williams, George Jones, and Lefty Frizzell. In 1967, at the age of 8, Randy began playing guitar. Two years later, he and his brother began performing at local clubs and talent contests, calling themselves the Traywick Brothers. Randy often fought with his father and soon dropped out of high school. He became a juvenile delinquent and was arrested for various offenses, including auto theft and burglary. Travis has since voiced regret for his past misdeeds.

In 1975, Randy won a talent contest at a nightclub, Country City USA, in Charlotte, North Carolina. The club's owner, Elizabeth "Lib" Hatcher, took an interest in the young singer, hired him as a cook, and gave him regular singing jobs at the club. During the late 1970s, Randy worked and sang at Country City USA.

In 1978, he recorded a self-titled album, Randy Traywick, for Paula Records. The following year, he released two unsuccessful singles, "She's My Woman" and "Dreamin'". Travis moved in with Hatcher, which put further strain on her already fragile marriage. She eventually left her husband and, in 1982, she and Travis moved to Nashville, Tennessee. It was during this time that an unlikely romance began to form between the two.

Travis would later comment, "I think we discovered how much we needed each other." He and Hatcher eventually came forward with their relationship and were married in a private ceremony in 1991. They divorced on October 29, 2010 after a 19-year marriage. Despite the divorce, their 34-year business relationship continues.