As a teenager, Green had quickly taken to the sounds of several Lone Star State performers: Robert Earl Keen, Waylon Jennings, Jerry Jeff Walker, and Willie Nelson. He started writing songs at age 18 while studying at Texas Tech, and was eager and earnest to make something more happen with music. After convincing his parents to loan him some money, Green recorded the album Dancehall Dreamer and independently released it in 1998, just as he was becoming a hot performer on the local bar scene. A year later, he wowed an audience of 2,000 people at Willie Nelson's Fourth of July picnic, and that magnetic event was captured for his second album, Live at Billy Bob's Texas.

Green continued to write and record as the 2000s dawned, releasing Carry On in 2000 and the covers album Songs We Wish We'd Written one year later (the latter was recorded and co-billed with Cory Morrow). In just a few short years, Green had sold over 200,000 copies without major-label support. Republic was so impressed with his grassroots approach that they signed him to a deal, and quickly released Three Days before the end of 2001. The album marked his first Top Ten country showing, sparked by a pair of Top 40 singles, "Carry On" and the title track. Two years later, Green joined producer Don Gehman (Hootie & the Blowfish, R.E.M., Nanci Griffith) for Wave on Wave; the title track reached the country Top Ten, and the album performed better than any of his previous releases. Just 15 months later, Green was back with Lucky Ones, which also bettered its predecessors, thanks to hit singles in "Don't Break My Heart Again," "Somewhere Between Texas and Mexico," and "Baby Doll."

In 2006, after a move to RCA imprint BNA, Cannonball was issued, followed by What I'm For in 2009, which found Green working with producer Dann Huff. Both albums performed well, although neither outperformed the gold certification of 2003's Wave on Wave. He revisited some of his favorite songs and songwriters for 2012's Songs We Wish We'd Written, Vol 2, a sequel to his 2001 album; it was released by noted bluegrass label Sugar Hill, as Green returned to the ranks of the independents. He recorded his next album on his own dime, and after completing the project, shopped it around to labels; he struck a deal with Relativity Entertainment, and Home was released in August 2015. Featuring guest spots from Lyle Lovett, Delbert McClinton, and Sheryl Crow, Home showed Green's fans were as loyal as ever; the album peaked at number five on the U.S. country charts. ~ MacKenzie Wilson