This irresistible ballad that makes Rosanne Cash go weak in the knees for her lover was written by her then-husband Rodney Crowell (the album's producer), and Hank DeVito, who also played electric and steel guitar on the record. But the idea came from Cash. She explained to Alanna Nash in the book Behind Closed Doors: Talking with the Legends of Country Music: "I love Judy Garland. I had this concept of it being one of these sultry, big-band type of things. We were gonna put horns on it, and it has this bedroom saxophone all over it that's just gorgeous. It evokes all these images of 'High Atop the Starlight Ballroom,' you know, ballroom dancing and everything smoky and your boyfriend just home from the war."
Geffen Records made history on June 27, 1994 when Aerosmith's "Head First" became the first major label song made available for exclusive digital download. Download speeds at the time were so slow it took around 75 minutes to download the track.