Songfacts®:

• This is a track from The Ballad of Dood & Juanita, a collection of country, bluegrass and mountain music tracks set in Kentucky in 1862. A Civil War-era song cycle of love and revenge, it tells an actual story, front to back through the lens of its two titular characters.
  
  It's also a nominal tribute to Sturgill's maternal grandparents and the old Westerns he used to watch with his grandpa. "I try to make concept records, he told Mojo magazine. "Or what I'd call cinematic records. This time, I wanted to write a story that flows, with all these different styles of traditional mountain and country and bluegrass music."
• Simpson croons the song from the perspective of Dood, a character inspired by the singer's grandfather. He sets off to rescue his wife, Juanita, after she's kidnapped by a bandit.
  
  Juanita, when I found you I was at my end
  So hold on, Juanita, I'll find you again
• Country legend Willie Nelson plays the guitar solo. Sturgill contacted Willie's son Micah, requesting him to ask his father to contribute to the song. The next morning he received a file in his email that read, "Trigger had fun." Trigger is Willie Nelson's guitar.
• Simpson wrote and recorded The Ballad of Dood & Juanita in less than a week, enlisting the same group of musicians who played on his two bluegrass collections, 2020's Cuttin' Grass, Vol. 1 and Vol. 2.