Still, music was just a hobby for Jackson -- he wrote songs only in his spare time. His wife Denise, a flight attendant, played a major part in setting Jackson down the road to Nashville. Around 1985, she encountered Glen Campbell in an airport and asked the singer for some advice for her husband. Campbell gave her the address and phone number of his publishing company. Jackson decided to sell his home and move to Nashville, bringing along a demo tape of some of his songs. Campbell's company was impressed by Jackson's singing ability, but suggested he hone his songwriting a bit. To support himself and his family, Jackson took odd jobs, including working in the mailroom of the Nashville Network and doing some session and demo work. The following year, he joined the staff of Glen Campbell Music.

When not writing, he performed in local clubs. After a while, he recorded a new demo tape with fellow songwriter Keith Stegall. The tape caught the attention of Arista Records, which was in the process of setting up a Nashville division, and he became the first artist on the label. Jackson released his debut album, Here in the Real World, in 1990; a year later it went platinum. It produced three chart toppers including "I'd Love You All Over Again" and "Someday." 1991 was even better: his second album Don't Rock the Jukebox went double-platinum within its first year of release. That same year, he became a member of the Grand Ole Opry.

In the fall of 1992, he released A Lot About Livin' (And a Little About Love), his most successful release to date, spawning no less than five Top Five singles, including the number ones "Love's Got a Hold On You," "She's Got the Rhythm (And I Got the Blues)," and "Chattahoochee." Jackson released a holiday album, Honky Tonk Christmas, in 1993. The following year, he delivered his follow-up to A Lot About Livin', Who I Am, which went double platinum within a year of its release. Who I Am spawned the number one hit singles "Summertime Blues," "Gone Country," "Livin' on Love," and "I Don't Even Know Your Name." In 1995, Jackson released The Greatest Hits Collection, which went triple platinum within a year of its release. Everything I Love surfaced in 1996, followed two years later by High Mileage.