He signed a writing and publishing deal with EMI Music Publishing a couple of years later, leaving Texas A&M in his junior year to relocate to Nashville, where he learned the writing and recording ropes in Music City while continuing to gig in the local bars and clubs. He self-released a second album, Memory RD., in 2005, along with Pockets of Pesos that same year, and even managed to graduate from Texas A&M that year as well. Livin' Like a Lonestar followed a year later in 2006, with We Bleed Maroon arriving in 2007.

By this time Smith was living back in his home state of Texas, where he gigged and toured constantly, becoming a major star on the Texas circuit. Don't Listen to the Radio was released in 2009, with a pair of albums, Live at the Chicken: 11-20-11 and Poets & Prisoners, arriving three years later in 2012. Dirt Road Driveway, written, recorded, and produced by Smith in his home studio, appeared in 2013, and included a pair of tracks, "Country Boy Love" and "The Country Boy Song," attributed to Smith's comedic alter ego, Earl Dibbles Jr. The year 2015 saw the release of 4x4, a four-song EP; the EP peaked at number six on the Country Albums chart and rose to 51 on the Top 200 Albums listing, while the song "Backroad Song" became a Top Ten country single, peaking at number one on Billboard's Country Airplay charts. In January 2016, Smith was named Hottest Artist to Watch in 2016 by the online magazine Taste of Country, and his major label debut Remington saw release on March 4, 2016. ~ Steve Leggett