This was Sugarland's first single. At the time, they were the trio of Kristian Bush, Kristen Hall and Jennifer Nettles. Hall left in 2005, and Bush and Nettles continued as a duo, with Nettles getting a lot of attention for her 2005 appearance on the Bon Jovi song "Who Says You Can't Go Home."
In our 2010 interview, when we asked Jennifer Nettles if this song was autobiographical, she replied: "Oh, you bet. It was not only autobiographical, but it was also a self-fulfilling prophecy in the sense that it was the first single, and it manifested itself in a way of showing that success. And granted, every artist – every person, really – can relate to having a dream and wanting to go after it, and wanting to make your folks proud, and having that be part of the joy of it. I know that for me, definitely a big part of the joy of my success is being able to share that enjoyment and that excitement with my family. And they're so proud. I love the story of that song and how it unfolded and how art definitely imitated life in that sense.
Regarding the lyrics, "Dear mom and dad, please send money, I'm so broke that it ain't funny," Nettles told us that she really did ask her folks for money - a little. Said Nettles: "You know, I'm the oldest child in my family, and we were always quite A-type personalities, and über-responsible. And I really tried to make my own way. Now, my mom at times would be generous and help me. She helped me out with my car insurance and those sorts of things. But for the most part, I really tried to make my own way." (Read the Jennifer Nettles interview.)