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 wasn't 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.
In February 2015, Watson made history when he released The Underdog, making him the first independent male artist to debut at number one on the Billboard Top Country Albums chart with a self-released and independently distributed and promoted album. The record sold more than 26,000 units in the first week.
By the end of 2014, the lead single from The Underdog, "That Look", which Watson wrote for his wife Kimberly, debuted in the top 10 of the Billboard Country Digital Songs Chart and was one of the most successful-selling independent singles.