5 Underrated Country Songs Guaranteed to Make You Cry

Photo by Priscilla Du Preez on Unsplash

Everyone has seen a list like this, but it’s always the same songs. “He Stopped Loving Her Today” is always number one on the list. While that is a timeless classic and one of greatest sad songs ever written, I want to throw in some variety with this list. I want you to discover new music that will make you cry. That doesn’t always mean it has to be sad either. There are plenty of songs in country music that can make you feel happy enough to cry, sometimes you even get that confused mix of sad and happy where you just turn into a wreck and cry for like 30 minutes straight, while differentiating constantly between happy tears and sad tears… maybe that’s just me. ANYWAYS, let’s just get straight to this list before it happens again.

  1. “Overalls” by Emily Scott Robinson

Emily Scott Robinson delivers this beautifully written song about the end of life so delicately, with her signature soft, calming voice. If you’ve ever known one of those southern old men who wear their overalls everywhere, this song will hit you hard. The song describes the wishes of one of these men. He knows he will pass soon so he reminisces on his life and tells everyone who loves him, not to worry, or mourn, just celebrate his life. I’ve known many old folks that this song fits to a T, several of which I’ve lost over the years, and I can never get over how much this song fits them. I always think of them when I hear it and it makes me misty-eyed every time. I highly recommend all of Robinson’s songs, as she has several I thought about including on this list, but ultimately settled on this one.

2. “Maggie’s Song” by Chris Stapleton

Chris Stapleton is by no means underrated anymore in the country music world, but this is a non-single cut off Starting Over so it isn’t one of his big songs, and I just had to include it. This song hit me like a ton of bricks when I was doing my first listen through Starting Over when it released. The performance I linked from the 2021 ACM Awards, features Miranda Lambert’s gorgeous, timeless voice backing the chorus, which makes it all the more emotional. I think most people who have ever owned a pet of any kind have always had that one that really stood out, and this song is an ode to a dog named Maggie who was just that. I was listening to this album for the first time on call with a friend, and I cried on that call because of this song.

3. “Waiting On June” by Holly Williams

Written and performed by Holly Williams, granddaughter of the legendary Hank Williams, “Waiting On June” is actually about her mom’s side of the family. The song is a wonderful, emotional, detailed story of her grandpa and grandma’s love, written from the perspective of her grandpa. There are so many lines in this song that will induce full-body goosebumps, including one of my favorite lines of all time from any song; “Charley Boy died in my arms, he saw Jesus, I saw blood.” She delivers the song with such a powerful voice that becomes very subdued when the mood of the lyrics call for it. It can make you cry happy, and sad tears both, all in the course of seven minutes.

4. “Georgia” by Katie Pruitt

This one may not be as universal as the others, but it’s just as emotional, and definitely made me cry the first time I heard it. Katie Pruitt is a phenomenal new writer on the scene who also boasts an angelic voice, and this single shows that in all it’s glory. Written about an all to familiar feeling of being spurned for simply being yourself in the place you live, more specifically, the small towns of the south. It delivers a powerful promise that even though it may not feel like it, you are loved, even if it’s not where you’re stuck now, somewhere you will be appreciated. I feel now is a good time to let you know that if you’re reading this, I love you, I appreciate you, and you have so much to give the world, just keep going. I’ve bawled to this song many times and I invite you to do the same, it’s nice to cry sometimes.

5. “The Bear” by Willi Carlisle

Willi Carlisle makes art. His lyrical ability is on par with the greats of old. His voice is full of pure emotion on most of his songs, but this one really stands out to me as his number one song to cry to. I’m not even sure how to describe what emotion this song elicits the most, as it really hits all of them. Nostalgia, happiness, and comfort, paralleled by longing for the past, depression, and near-manic frustration, caused by PTSD. It is a whirlwind of a song in the best way possible, and never fails to bring a tear to my eye and give goosebumps.

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Those are five of the more underrated country songs to cry to in my opinion. I hope I was able to give you a new song to cry under the covers to. I know I personally have done that to every one of these at some point. Thanks for reading and if you liked this list, comment and let me know, and maybe I’ll make another one and feature five more songs!




I’m Ethan, and this is my (mostly) country music blog: Critical Country | Top Writer in Country Music and Music | Contact me at ethansilvers@yahoo.com

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Critical Country

Critical Country

I’m Ethan, and this is my (mostly) country music blog: Critical Country | Top Writer in Country Music and Music | Contact me at ethansilvers@yahoo.com

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