Watson was born in Amarillo, Texas, and graduated from Randall High School. He then attended Lubbock Christian University and Abilene Christian University, where he began learning guitar, after playing junior college baseball in New Mexico. Watson's earliest musical influences were the classic country records by George Jones, Merle Haggard, and Willie Nelson his parents listened to, and the gospel hymns he sang with his family in church.
He released his first album, Aaron Watson – Singers and Songwriters in 1999 and followed that up with Texas Cafe in 2000. It was not until this third album, Shut Up And Dance, in 2002, that Watson gained radio airplay and attention nationwide. Following that record's success, he released The Honky Tonk Kid, produced by Ray Benson and featuring Willie Nelson on guest vocals.
He worked various gigs around Texas before releasing his second album, A Texas Cafe. The follow-up, Shut Up And Dance, was a regional sales success. His 2004 album, The Honky Tonk Kid, was produced by Ray Benson and features an appearance by 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 US Billboard country charts and No. 50 on its Heatseekers chart.

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