Jackson began his career in the mid-1980s, signing with Nashville's Arista Records in 1989. His first album, "Here in the Real World", was released in 1990. The album produced four singles, all of which reached the Top 10 on the Billboard Hot Country Singles chart.
In 1991, Jackson released his second album, "Don't Rock the Jukebox", which was even more successful than his debut. The album produced six singles, all of which reached the Top 10 on the Billboard Hot Country Singles chart. The album was also certified 3x Platinum by the RIAA, making it Jackson's first Platinum-selling album.
In 1992, Jackson released his third album, "A Lot About Livin' (And a Little 'bout Love)", which was also very successful. The album produced six singles, all of which reached the Top 10 on the Billboard Hot Country Singles chart. The album was also certified 4x Platinum by the RIAA, making it Jackson's second Platinum-selling album.
Jackson continued to release successful albums in the 1990s and 2000s, with his most recent album, "Where Have You Gone", released in 2009.
Throughout his career, Jackson has won numerous awards, including 22 Country Music Association Awards, 2 Grammy Awards, and 2 Academy of Country Music Awards. He is also a member of the Grand Ole Opry.