This was written by Jim Lauderdale, who recorded the song on his 1991 debut album Planet of Love. Strait recorded it for the 1992 movie Pure Country, where he stared as a Country singer looking to get back to his roots. Straight also recorded Lauderdale's "Where the Sidewalk Ends" for the soundtrack, and has recorded many more of Lauderdale's songs since, including "What Do You Say To That" and "Twang."
In our interview with Jim Lauderdale, he told the story behind this song: "I was reading this book about Gram Parsons, and there's this story by this lady, Pamela Des Barres, telling about how he was playing George Jones' records for people that had never heard him before, and he started crying, and he said that's the king of broken hearts. He's one of my favorites, so I wrote that song as a tribute to Gram and George Jones."