Pistol Annies is an all-female trio comprising Miranda Lambert and fellow songwriters Angaleena Presley and Ashley Monroe. Lambert explained the inspiration for this song to Billboard magazine: "I started thinking about how Southern boys just have a certain charm about them," she said. "It's one of our favorite songs on the album. Every time I play it live anywhere, especially below the Mason-Dixon, people love it."
The lyrics to "Heartbreak Hotel" were written by a steel guitar player who was once a dishwasher repairman. He was inspired by a newspaper story about a man who killed himself and left behind a note saying only, "I walk a lonely street."