Songfacts®:

• Reilly is a singer/songwriter from Illinois who various publications have described as "genre-bending" and "outlandish." When we asked him to write about some of his songs, Reilly replied, "To be honest I can't really remember inspiration or much from the time I wrote these songs. Having said that I will make some s--t up that is mostly true."
  
  With that caveat, here's his description of this song:
  
  "I wrote a song and called it 'The Ballad of Jack and Haley.' It was certainly inspired by a friend of mine whose name is Jack. See this friend of mine, Jack, was growing weed in his basement. Jack had a lot of talents, really. Could do just about anything so I enlisted him to help me organize my garden. One day last summer, he was going to come over because I was putting up some fencing and he was gonna help me lay out some vegetables... kinda help me map out my garden. While I was waiting for him to show up, I was playing the guitar and when he walked up to me I jokingly sang, 'Well Jack he grew an indoor garden in the basement of his home.' After he left, I continued to think about Jack and what he was doing to provide for his family. I finished the song... it's really about a father and daughter... kind of a straight-ahead story. David Lowery from the band Cracker was storing some gear at my studio and I asked him to sing on it with me. He had to say yes or I would have thrown his gear out in the f--king street. He did say yes and I love the way the choruses sound with Lowery croaking away with me. Two smooth croakers."