Songfacts®:

• This autobiographical cut finds Aaron Watson recalling some of the events that have happened during his career as a country music singer. "That song is kind of like a declaration of independence, but with no sour grapes involved. It's not a jab at Nashville," he told Billboard magazine. "We have lots of allies there, and my booking agent has been there for the last decade. My distribution company is based there, we're playing the Ryman and the Grand Ole Opry in the next few months, so the song is not really about a region in particular, although I do say I would rather be a fence post in Texas than the king of Tennessee. That was actually a saying that Sam Houston had said, and it kind of inspired me to write a song about my experiences in the music industry."
  
  "It is a true story," Watson added. "I had a guy at a major label on Music Row pretty much slam the door in my face and tell me I wasn't going to amount to too much. That hurt my feelings, I'm not going to lie. I grew up listening to George Strait, Merle Haggard, Alan Jackson, Keith Whitley and a lot of the great records that came out of Nashville. Having that experience of being told that you don't have what it takes will do two things: It will stop you in your tracks, or you can use that to fuel your passion. I decided at that point that it might not have turned out like I was hoping, but I was going to go back to Texas, and we're going to write the best songs we can write and record the best albums we can record. We're going to work our butts off and just do things the old-fashioned way - earn it one honky-tonk at a time. I feel like we've developed a solid fanbase that grows year after year."
• When The Underdog debuted at #1 on the Billboard Country Albums chart, Aaron Watson made history. He was the first solo male artist to land at the top spot with a self-released and independently distributed and promoted album in the record's debut week.