Watson was born in Amarillo, Texas and attended Abilene Christian University, where he began learning guitar, after playing junior college baseball in New Mexico. He gigged around Texas before releasing his debut album, A Texas Cafe; the follow-up, Shuttupanddance, was a regional sales success. His 2004 album, The Honky Tonk Kid, was produced by Ray Benson and features an appearance from Willie Nelson. Watson's band is called the Orphans of the Brazos; they appear on his 2005 album, Live at the Texas Hall of Fame. In 2006, his San Angelo release hit No. 60 on the U.S. Billboard country charts and No. 50 on its Heatseekers chart.