“You Don’t Know Jack” – Tailgates & Tanlines

“So brother just be glad // and tonight hold your kids, kiss your wife // and when you talk to God // Count up all your blessings // And thank the good Lord that // You don’t know Jack”

When we talk about the storytelling aspect of country music, this is a prime example of what we mean. The way Bryan is able to tell the story of these two men as if we know them or are them is beautiful, as is the play on words of not knowing Jack – as in nothing about the situation as well as the bottle. It’s the unique way of saying that you’ll never know someone’s whole story or what they’re going through.

“We Run This Town” – Crash My Party

“We thought we made the world go ‘round // Nothing but a bunch of time to kill // Sit up on a hill // Make a toast, drink it down // Say, yeah, man, we run this town // high-five and look around // Damn right we run this town”

Bryan definitely has a good amount of nostalgic songs, but this is one of our favorites. It perfectly embodies the feeling of being seventeen again, hanging out with your friends every day, and having no worries in the world. 

“Dirt Road Diary” – Crash My Party

“It’s right here in my dirt road diary // It ain’t a book underneath my bed // Just a dusty memory lane burned in my head”

There are too many great songs to choose from on this album, but “Dirt Road Diary” is one of the most raw and honest songs from Bryan – he is quite literally saying that he is an open book. He shares his story and says he simply is where he came from- which means it also has the perfect amount of nostalgia. 

“Land of a Million Songs” – What Makes You Country

“So you packed up your pickup and crossed that Tennessee line // You’re always searching for a little something different to say” 

This song is unique compared to the types of tracks that we’re used to hearing from Bryan. I feel like a lot of times people can generalize Bryan’s songs to being your basic country songs about girls, beers, hunting, fishing, and trucks. Not to say that’s not part of his identity either (I mean isn’t that what makes you country?), but I think that can make fans overlook songs like this one and the others on this list that hold a deeper meaning.

Much like Tim McGraw’s “Damn Country Music”, “Land of a Million Songs” flips the script on the thrill of making it in the industry and highlights the struggles to get there, all that is given up to make it possible, how slim the chances of making it really are and how all of that circles back to writing and playing music because make it or not, that’s what you’ll always do – whether others are listening or not. 

“For A Boat” – Born Here Live Here Die Here

“And Daddy saying ‘son, don’t they bite just fine right here?’ // He’d say, “Love what you got, buddy, not what you ain’t’ // And just about then that bobber would sink // And that outboard dream of mine would disappear // I grew up pretty lucky as far as lucky goes // Too broke for a boat”

About a shared love for fishing, and the relationship and memories that it created, this song is simply about appreciating what you have over hoping for things that you don’t and realizing that you don’t need the fancy things in life to be considered one of the lucky ones. Rather, looking back on it, that’s precisely what made you one of the lucky ones.