This was written by Big Kenny (Kenny Alphin) of the Country music duo Big & Rich. The lyrics tell of a man who is upbeat despite being down to his last dollar. Big Kenny wrote this at a time when he was struggling financially himself. He was in Las Vegas on New Years Eve of 2002, about to open the "Alabama Farewell Tour," with only $200 to his name. Kenny decided the only way he'd be able to keep up with his rent and other overheads was to make it big on a black jack table. At first he won close to $1,000, but eventually he lost everything except $21. He generously left the dealer with a $20.00 tip, leaving him with one dollar to his name. Kenny said in the song's publicity materials: "That night as I looked down at the sole breaking off of my shoe it hit me like a ton of bricks. But with that realization came the freedom of knowing that I also had nothing to lose."
Big Kenny added in the publicity materials: "I'll never forget the day I played him (Tim McGraw) the song. We were at Blackbird Studio and Tim was making a new album. As we sat together in my truck, I played him a couple of the songs that I was recording. The second song I played was 'Last Dollar.' He looked over at me and said, 'Are you gonna' let me record that?' About 6 months ago, Tim called me again to come by his home and he played me 'Last Dollar.' When I heard the kids at the end of the song, I nearly lost it. That moment of reflection in Las Vegas all that time ago gave me the hope to keep going and now 5 years later, that hope is a hit song for my friend Tim McGraw."
Tim McGraw's daughters sing along with him at the end of this song. CMT News asked the Country star how this came about. He replied: "That was a lot of fun. My girls and [co-producer] Byron Gallimore's girls are singing on there. It was just a wild idea at the end of doing the song. It sounded like it would be fun. And the song is such a lighthearted, fun song, anyway. They really liked it. They were going around singing it. Big Kenny wrote it, and when Big Kenny gave me the CD of it and I was listening to it over and over and over, the girls were just singing it every time they heard it. They'd tell me to play the demo. I think they liked Big Kenny better than they do me. But I just thought it was cute, and they did a great job on it."
This was McGraw's first Country #1 since "Back When" in 2004.