After high school, with his father's help, Jason Aldean and his band performed in college towns in Florida, Alabama, and Georgia, and then further up the southeastern seaboard. With one of the band's members, Justin Weaver, Aldean began writing songs. In 1998 he performed his original songs at a showcase staged by Atlanta nightclub The Buckboard. He was approached by Michael Knox, then of the Warner-Chappell song-publishing company. After signing with Warner-Chappell, Aldean moved to Music City on November 1, 1998 at age 21.
A month after moving to Music City, Aldean was offered a recording contract but was subsequently dropped. He signed with another label but again was dropped in 2000. Various showcases failed to bring him a contract. Finally, Lawrence Mathis spotted Jason at one of the showcases at The Wildhorse Saloon in Nashville. Mathis signed as Aldean's manager. Still frustrated and discouraged with his struggling career, Aldean gave himself six months before planning to leave Nashville and return home to Georgia. Soon after, he was offered a deal from Broken Bow Records in Nashville.
Aldean's first single, "Hicktown", was released in early 2005. It served as the lead-off to his album Jason Aldean, and reached a peak of #10 on the Billboard Hot Country Songs charts. The album also produced his first Number One hit in "Why", as well as the #4-peaking "Amarillo Sky". Jason Aldean also sold more than one million copies in the United States, and was certified platinum by the RIAA.
Aldean spent most of January 2007 in the studio with producer Michael Knox to finish his second album, Relentless. The album's lead-off single, "Johnny Cash", was released in mid-2007, peaking at #6 on the country charts; its followup, "Laughed Until We Cried", has become his fifth consecutive Top Ten hit. Relentless has also been certified gold by the RIAA, and its title track has been released as its third single