Gray was signed to Broken Bow Records, who released his debut album, Lookin' for Trouble, in February 2000.[3] Its first single, "I'm Lookin' for Trouble", peaked at number 75 on the BillboardHot Country Singles & Tracks chart.[1] The album received a mixed review from Chet Flippo of Billboard, who wrote that "despite a certain unevenness here, Gray shows considerable potential, which is probably due to the many different configurations of five different producers who worked on the album."[4]
