This was written by Gary Hannan, Phil O'Donnell and Trent Willmon. Prior to the release of this song, Willmon had 4 Top 40 singles in the US country chart as a solo artist, the most successful being the #27 placing of "On Again Tonight" in 2006.
In an interview with the Winstock Festival website, Troy Gentry said that as soon they heard this song, the duo knew it was a good thing. He explained: "When we heard the song, we knew it was a hit for Montgomery Gentry off the bat. A buddy of ours, Trent Willmon, a writer on that song, brought the song to us and we just kinda knew it was a hit. In listening to the song, it just reminds us of the days growing up - it reminded me of all the do's and don'ts coming from mom and dad; you know, the path of life that shoulda been taken."
Phil O'Donnell told AOL the story behind this song. He said: "The idea actually came from my co-writer, Gary Hannan, but a lot of the places in the song are places that I pass everyday. For example, Tuffy's is where I sometimes fill up with gas, and I've stopped there and seen kids, who I know are not twenty-one, with beer. The 'step-side truck that can't jump a ditch' was actually an Oldsmobile that I put through a fence one night. Another very true part of the song is in the line 'a Sunday sermon can turn a life around.' I turned my life over to the Lord in 1993 and I consider that a major turning point in my life."