Like many a fine songwriter before him, Thompson has lived a lifetime of experiences in his short time here. With family tragedy of Southern Gothic proportion, Thompson was exposed to addiction and mental illness from a young age, ultimately losing both his maternal grandfather and his mother to the diseases. The heartbreak and uncertainty that haunted him throughout his youth permeate the writing on this album. 26 Years is Thompson's coming of age. "Writing and recording these songs allowed me to come to terms with the end of my childhood and the beginning of the rest of my life," Allen explains in his liner notes.

Throughout his life Thompson recalls his most vivid memories through the music that he has attached to them. His grandfather would introduce him to his many of his musical influences, playing the records of Hank Williams, Merle Haggard, Bill Monroe, Patsy Cline, and Buck Owens for Allen and his brother. Time with his father was often tied to the music his dad would play for him on the cassette player in the car. "On that first visitation, my dad was so excited about this guy he had seen play just a few days before in Richmond, VA. The record was Steve Earle's Guitar Town, and it changed my life. It was full of songs that felt like they had been written about us: Being away from your children, divorce, trying to survive in the Trickle-down era in a small town." Thompson credits how Earle's songs touched his father as being the catalyst for wanting to do that same thing with his own life.

Allen relocated to Nashville in 2007 to complete work on his eponymous album which was released in 2008 as a follow-up to 2006's Highway. Following that release, Allen recorded 2 tracks at the famed Ardent Studios in Memphis with Jeff Powell (Afghan Whigs, Primal Scream, Bob Dylan, the Allman Brothers Band) at the helm. Despite the wonderful experiences he had making these recordings, Allen decided he wanted to make a stripped-down, acoustic record in order to appropriately showcase the lyrical content of this new batch of songs. In January of 2009, he enlisted the help of Eric Masse and Adam Popick and entered Cabin on the Hill Studios in Franklin, TN to record what would become 26 Years.