Steve Earle wrote this song for the TV series Nashville, where it was performed by Sam Palladio as the character Gunnar in the Season 1 episode A Picture from Life's Other Side in 2013 and included on that season's soundtrack album. After recording another song for the series the next season ("Lookin' for a Woman," which wasn't used), Earle decided to use those songs as the basis for his 2017 album So You Wannabe An Outlaw. He had been listening to a lot of Waylon Jennings at the time, so the country feel of those songs fit the style he was going for.
The song is about a prisoner whose only solace is that his mother will never see him in jail, as she died when he was 13.
T Bone Burnett, who was the musical director on Nashville, asked Earle to write this song for the show. Earle never watched the show, but he did get a script. "He said, 'I need a song. This character's brother is getting out of prison, and he's going to have a song, and it's supposed to a pretty good song that he wrote while he was in jail," Earle said in a Songfacts interview. "And for some reason he thought I was qualified to do that. He knows I can write a song to order, so it's not really just a jail thing."