Man, I love this song. That Willie Nelson knew what he was doing. I was driving from Branson to Memphis in 2014 the first time I really heard Sad Songs and Waltzes. We were probably half way finished tracking the record, and I went out on tour for a week by myself. I spent a lot of time in the car alone, thinking about how to finish up the album. This project was a departure from everything I'd ever done. I was going from indie-space-rock to some combo between americana and alt-country. I knew this "laidback lilt" might surprise the bulk of my fans, but when I heard this line: "though my record may say it, no one will play it" I made up my mind. I would finish what I started, even if the record wasn't a smashing success. I said some things in "It Did Me Well" that I'd been waiting to say for a long time. They had been weighing me down for years, and for whatever reason all the other times I tried I just couldn't. But now I could, and Willie helped me do it.