4 Country Songs From Every Generation That Will Take You Right Back to High School

Country music tells a story better than any other genre. It’s in the country community’s bones to deliver truth to its listeners. There are many stories to tell, but the best ones are relatable to everyone. If there’s one thing that is sure to hit home, it’s a song about the high school experience. Below, find four country songs, from every generation, that have no trouble taking you right back to your high school days.

Videos by American Songwriter

“Half of My Hometown” (Kelsea Ballerini and Kenny Chesney)

Kelsea Ballerini recalls her high school days in one of her name-making country songs, “Half of My Hometown,” featuring Kenny Chesney. Half of my hometown’s still hangin’ around / Still talkin’ about that one touchdown / They’re still wearin’ red and black / “Go Bobcats,” she sings in this sentimental song. Though Ballerini is less removed from high school than some of us, no matter how long it has been since you graduated, you can still remember little details about what molded you when you were young.

“The Boys of Fall” (Kenny Chesney)

A big part of the high school experience (for most people, anyway) is game days. Sports have a way of uniting people around a common cause. No matter how set apart you were from your classmates, a win from the home team would put all of that to bed. Chesney sings about being a part of high school sports in his country song “The Boys of Fall.” To get to wear those game day jerseys down the hall / Kings of the school man, we’re the boys of fall, Chesney sings. We can’t all boast about having been on the starting lineup, but the nostalgia is there regardless.

“Check Yes or No” (George Strait)

We all know that flushed feeling of young love. It can be hard to navigate those feelings, and high school isn’t always the best background for romance. George Strait perfectly sums up the nervousness and hope that comes with a crush. Though Strait focuses more on childhood and marriage than high school, the same sentiment in this country song applies to our teenage years.

“Old School” (John Conlee)

High school is a time of “what-ifs.” Not all of those hopes and dreams pan out, but they are certainly palpable. In his song “Old School,” John Conlee sings about his high school sweetheart. They don’t end up together right away, but later reconnect. Despite the sticky ending of this song, the references to old times will warm the heart of anyone. I can remember us cruising through town / In your daddy’s car with the top pulled down / Looking so cool / We came from different sides of the track / But we still held hands out back of the old school, Conlee sings.

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