A Boot and a Shoe was the last of six Sam Phillips albums produced by T Bone Burnett, her husband from 1989 until 2004, when the album was released. This song finds her dealing with that relationship. "When you love someone, that love doesn't completely disappear when you break up," she told Songfacts. "The hardest thing is to not kill that love because you are hurt, but to let it be and to let the hurt go. In other words, I like to reach for the almost impossible."
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