Songfacts®:

• Gill penned this song with his old songwriting partner Pete Wasner. He said: "We've been making music and traveling and writing songs together for 30 years. We have always had a great kinship musically. More than anybody, when we play together, we know exactly what the other one is going to do. It always feels right to play music with him and write songs with him."
• The song pays tribute to Billie Holiday and was inspired by her biopic, Lady Sings The Blues. Gill explained: "When I was 13 or 14, we had a little movie theater a block from my house. One of my favorite movies at that time was Lady Sings The Blues with Diana Ross. At that time, I had never heard of Billie Holiday. Anyway, I saw that movie 50 times. I was just mesmerized by this music and became a huge fan of that bluesy big band sound. I was a young sponge and I couldn't get enough of it. I wanted to pay tribute to Billie, so the last verse finds a way to use some of her song titles like 'God Bless This Child' and 'Ain't It Nice What A Little Moonlight Can Do When The Lady Sings The Blues.'"
• The song features a lot of bluesy guitar playing by Gill. He said: "I feel like my guitar playing on this record has taken a step up. It's interesting now, 30-something years into a career, that people are really starting to get a great sense of my guitar playing. It's almost as much a guitar record in spots as it is a singing record. This is one of the tracks that is kind of funky and Little Feat-ish or Steely Dan-ish with a lot of guitar playing on the end of it." (Quotes from the now-shuttered Roughstock.)