Songfacts®:

• When Nail first heard this reflective Rick Brantley, Tia Sellers and Mark Selby-penned song about a guy feeling like he'd got the weight of the world upon him, it reminded him of when he was going through a bout of depression. He told Roughstock: "You're crying out, drinking too much, putting on weight, in an effort to get somebody to recognize it and pick you up. This guy says, 'I'm lost. I need somebody to help me through this. I'm up on this hill, looking down below. Is anybody listening out there?' I remember being there. I would go home to Missouri because that's where I felt the most normal. My life had gotten so complex and I wanted to be back in that simply structured town, where everything was the exact opposite of where I was. I was trying to force this simple quality back into my life. It was a no-brainer to record 'Half Mile Hill.'"
• Nail was hesitant to cut this song, as he felt there were a number of reflective songs reflecting the past on his first album, and he wanted to stay away from the subject on his sophomore release. He explained to The Boot: "It's a very honest and personal song and something I didn't ever want to relive again. But somebody told me, 'That's an important part of your life, and rather than run away from it you ought to embrace it, if for no other reason than it's always gonna serve as a reminder of what you've overcome.'"
• When Nail finally decided to record the song, he had just two takes on the vocal, as he felt it is the type of song that needs to be raw, and it didn't matter if he hit some wrong notes.
• Speaking to The Boot, Nail recalled to the Boot dating a girl one summer when he was 17, who had no interest in settling down, but would always give him enough to keep him hanging on. He said: "To me, 'Half Mile Hill' is about finding yourself and coming to the crossroads where you look back and you go, 'That moment in my life sucked, and maybe in this moment I'm miserable, but I can see the light at the end of the tunnel and all of this is going to make me a stronger person.'"