Jackson's wife, Denise, got him connected to Glen Campbell, who helped him jumpstart his career. His first album, 1990's Here in the Real World, was a major hit, as was his second (1991) album, Don't Rock the Jukebox. His 1992 release, A Lot About Livin' (And a Little About Love) was a smash success, spawning five major singles with "Chattahoochee" being the most enduring and successful. After a few more hit albums, Jackson again rocketed to fame with "Where Were You", a song about the September 11, 2001 Terrorist Attacks, which became a hit single despite much criticism for jingoism and hollow patriotism; including an unflattering portrayal in an episode of South Park.
Although Jackson has been characterised as a "hat act", his influences go deep into the roots of country music and his songs have been recorded by some of the greats like Charley Pride, who recorded "Here In The Real World". He has sung with George Jones on the award winning "I Don't Need Your Rockin' Chair". His sense of humour comes through on the satirical description of the wannabees who cynically jumped on the country music bandwagon in the 1990s, "Everybody's gone country/Yeah we've gone country/The whole world's gone country." ("Gone Country").