Born in Pensacola, Florida, Tippin was raised on a 120-acre family farm in South Carolina; his chief influences included Jimmie Rodgers, Hank Thompson, and Lefty Frizzell. At age ten, he began playing guitar and performing in local groups. At age 20, he was working as a commercial pilot, but switched to music before obtaining his Airline Transport Rating. During the early '80s, he wrote songs for various Nashville publishing outfits. In 1986, he permanently moved to Nashville, where he eventually became a staff writer at Acuff-Rose. He also tried to land his own recording contract, with little success. Eventually, his demo tape arrived at RCA, who offered him a contract.

Tippin's debut single, "You've Got to Stand for Something," reached the Top Ten in 1991 and was followed by an album of the same name which spawned two other minor hit singles and peaked at number 25 on the country charts. Read Between the Lines, his second album, was released in 1992 and contained his first number one single, "There Ain't Nothing Wrong with the Radio." Read Between the Lines climbed to the Top Ten and crossed over to the Top 50 on the pop album charts; it went platinum in 1993 and produced two more hits, including the Top Five "I Wouldn't Have It Any Other Way." In 1993, Tippin released his third album, Call of the Wild, which went gold four months after its release. Lookin' Back at Myself appeared the following year, while Tool Box, his fifth album, was released in 1995. What This Country Needs followed in 1998.