This song was written and originally recorded by Willie Nelson on his 1990 album Born for Trouble.
This is a song about a guy who goes home with a 10 out of 10 girl. When he wakes up, he finds she's a 2. Chesney explained to Newsweek: "That's definitely autobiographical. I admit it's not the classiest song I've ever recorded. It's an old Willie Nelson song. This is probably going to be my beer-goggles song. There are girls who are going to listen and say, you know what, I've been there, too. A girl leaving a bar, thinking she's left with Brad Pitt and waking up with me or you." He added: "That was my reality in college a lot. All the guys who have been on the road with me, when I played this song, their jaw dropped."