October 9, 2012, Aaron Watson released Real Good Time. It achieved national attention, and was the best performing album for Watson to date, peaking at No. 9 on the US Billboard Country Albums. It was also his first to break into the top twenty for independent albums. It had sold 32,000 copies as of February 2015.
In 2014, Aaron Watson released the lead single from his album The Underdog, “That Look”, which he wrote for his wife Kimberly. The single debuted in the top 10 of the Billboard Country Digital Songs chart and went on to become one of the most successful-selling independent singles by the end of December 2014.