Kenny Chesney: Songs That Should’ve Been Singles

The process of choosing a single for radio is often as arduous a task as writing the song. Each month, Sounds Like Nashville will feature a different artist and explore songs from his or her catalogue that we wish made it to radio. Make no mistake, this is no critique of the artist or label, it’s simply a list of songs we love so much that we think deserve to be in the spotlight. This month, we take a closer listen to Kenny Chesney’s back catalogue and find eight gems that warrant airplay.

“I Remember”

The second track off Chesney’s widely popular 2002 release No Shoes, No Shirt, No Problems, “I Remember” showcases the island lover’s ability to tackle a power ballad. Well known for his laidback, fun side, “I Remember” has the singer nostalgic for an old love. Written by Brad Crisler and James LeBlanc, the piano driven song exemplifies Chesney’s ability to switch gears effortlessly from previous party songs to more serious topics, like regretting saying goodbye in a relationship.

“Dancin’ for the Groceries”

“Dancin’ for the Groceries” is not a song typically heard on country radio which is all the more reason why it should have been released. A poignant tale of a single mother who dances to pay the bills, “Dancin’ for the Groceries” is a heartfelt song that shares that the mom is “dancing for the braces so her kids can have a perfect smile someday . . . smiling while she dances is the price she has to pay.” Written by Nashville hitmakers Brett James and Don Schlitz, “Dancin’ for the Groceries” is a song that sticks with the listener long after it is over.

“Round and Round”

Another story song, “Round and Round” has Chesney singing of two people on opposite ends of the spectrum. There’s a woman who’s stuck in a love affair who wants to be single and another lady who is a lonely soul and hopes for a ring on her left hand. Later, a young man is wishing he could speed up the hands of time while an old man desires going back to his youth.

“Round and round and round and round we go. Why we can’t be satisfied I don’t know. From the day we were born it seems like it never stops. Why we always want something we ain’t got,” he sings on the gritty, guitar-driven track. An all too real song, it’s one that needs to be heard.

“Makes Me Wonder”

Sometimes a guy and a girl can just be friends. At least, that’s what Chesney sings about on “Makes Me Wonder.” Chesney co-wrote the song with Wendell Mobley and Neil Thrasher as he admires a longtime friend that has him wondering why he and she aren’t in love after spending some time together.

“I got on that airplane, you got in your car. Looked out on that city wonderin’ where you are. And if you’re feeling like me, just a little bit sad. I already miss you, now what’s up with that? Makes me wonder why we’re not in love,” he sings as their visit comes to a close.

“Never Gonna Feel Like That Again”

Another ballad that has Chesney looking back, “Never Gonna Feel Like That Again” is a song that begs the listener to live in the moment. Whether he’s talking about Friday night football, prom or having children of his own, Chesney is never preaching. Instead, he tells a story that urges the listener to “grab each moment” as they can.

“Time’s rushing by me like the wind, never be as young as I was then. No, I’m never gonna feel like that again,” he sings alongside soaring guitar and pedal steel.

“Boston”

“Boston” appears on Chesney’s Be As You Are (Songs from an Old Blue Chair) album, which was intended as a side project. Co-written with Mark Tamburino, the song follows a girl formerly from Boston who has made a home for herself in the islands. The mostly acoustic track highlights Chesney’s deep vocals coupled with memorable steel drums and lightly finger picked guitar, transporting the listener to the islands. With a beat so enjoyable and a lifestyle so laidback, we can’t blame the girl in the song from escaping from New England to a place near the water.

“Drink It Up”

Chesney is the king of summer and having a good time, so it only makes sense that he’d have a song called “Drink It Up.” Surprisingly, this song never made its way to radio and it’s a shame. The upbeat track is a summer anthem that urges us all to live out every single minute while we still can. “Light it up, burn it out. That’s what life’s all about. Man, you can’t just take a little sip — fill your cup, drink it up,” he says. If Kenny Chesney says so, we should follow orders.

“If This Bus Could Talk”

The final track on Chesney’s last album The Big Revival, “If This Bus Could Talk” tells the story of the singer’s career and life on the road. His bus was there in ’93 for his first big tour opening for Patty Loveless when he was just a starry-eyed dreamer bouncing off the walls. Then, there were many summers where he headlined his own tour. Chesney wrote the song with Tom Douglas, which gives it even more weight as each line was taken from real life. A sentimental tune that gives a glimpse at the depth of Chesney, it’s a song of welcomed nostalgia.