This song finds Isbell contemplating both his parents and his in-laws early entry into parenthood. He explained to Uncut magazine: "Both sets were very young when we were born. The time my mother spent raising me likely cost her a lot of opportunities, and even though she'd never be resentful of that and it's obviously not my fault, I've benefited from it, so I've felt guilty. I think my wife Amanda, has at times felt that way about her mother. The song is my way of looking those things in the eye and dealing with them."
Country star Slim Whitman's version of the 1920s song "Rose Marie" spent 11 consecutive weeks at #1 in the UK in 1955, a record until 1991 when Bryan Adams’ "(Everything I Do) I Do It For You" spent 16 weeks at the top.
"Pretty In Pink" by Psychedelic Furs was released in 1981. Five years later, it inspired a movie of the same name starring Molly Ringwald, Andrew McCarthy and Jon Cryer. The song was remixed for the re-release to have more Pop appeal.