5 More Underrated Country Songs Guaranteed to Make You Cry.

Critical Country
4 min readJan 8, 2022

Returning to tears.

Photo by Uriel Soberanes on Unsplash

One of my first uploads to this blog was “5 Underrated Country Songs Guaranteed to Make You Cry.” Some of ya’ll liked that list and gave some good suggestions for a second list, so here it is!

  1. “The Overpass” by Ward Davis

Thanks to Steven Hale for recommending this gracefully written, sorrowful, heart-wrenching song.

This is a tear-jerking guitar ballad about a man who lost everything to his addictions and bad habits, and has ended up living under an overpass. It touches on the monotony of every day under the overpass being the same. Being sober reminds the man of how far he’s fallen, so he makes sure to stay drunk, which makes him stay stagnant.

The lyricism throughout the whole song is just amazing. Davis’ delivery of each line brilliantly captures every bit of the emotion as well. Once you really digest each line, and start to put yourself in this man’s shoes, that’s when it really hits you.

2. “William and Wanda” by Cody Jinks

Man — Krystal Mossbarger came heavy with this one when she recommended it. I cried on the first listen to this one so it definitely belongs here.

The song is somewhat reminiscent of “Waiting on June” by Holly Williams which I included in my first list. “William and Wanda” is another gorgeous acoustic arrangement. The lyrics are written from the perspective of “William and Wanda.” They are so simple, but so, so powerful.

First we hear from Wanda, she’s telling William how long she and their “little boy that died on his birthday” have been waiting on William to arrive. She tells of all things she’s done while waiting on him, and how they haven’t been sad or crying; as this doesn’t happen where they are, but they have been anxious and excited for him to arrive.

Then William starts talking to Wanda in a perfectly “old man” type of way. Telling her to just calm down and stop picking at him. He talks about his time on earth and how he did cry and missed them, and hoped he’d be with them again.

Again, this one is so beautiful and the tears flow every time I’ve listened to it.

3. “Fire Away” by Chris Stapleton

Another great suggestion by Krystal Mossbarger.

I included a Chris Stapleton song in my last one and I mentioned how it’s hard to call anything he does “underrated”, as he is a giant in the country music world right now, but some of his stuff does fly more under the radar than his other hits.

“Fire Away” is written from the perspective of someone in a dedicated relationship, telling their significant other to “fire away,” and unload all their stress and inhibitions, they can handle it.

While the song is very emotional, especially with Stapleton’s signature, powerful voice, the thing here guaranteed to make you cry is the music video.

Delivering a powerful message about the five signs of emotional suffering. I won’t give any details so I don’t spoil it, as I highly encourage you to watch it yourself.

4. “Tell Lorrie I Love Her” by Keith Whitley

I just recently posted a piece on Keith Whitley, so I have been listening to his discography a ton lately. This song isn’t one of his big hits, but it is gorgeous nonetheless, which makes it a great fit for this list.

“Tell Lorrie I Love Her” was written by Keith Whitley for his then-fiancé, but eventual wife; Lorrie Morgan. He only recorded it in his home, as a rough demo to give to the man who was going to play it at their wedding.

He talks about how if he is ever on the brink of death, his first wish would be for someone to “tell Lorrie I love her.”

Whitley tragically passed away at just 34 years-old, leaving Lorrie Morgan, a son, and step-daughter behind. “Tell Lorrie I Love Her” was released publicly in 1990, on his posthumous compilation album; Keith Whitley Greatest Hits.

It’s not often you have a song where the story behind it is what makes you cry. Hearing this song, and knowing he died so tragically young is just soul crushing. It’s hard to tell if it’s happy tears from his last wish coming true with that song being on record, or if it’s just pure sad tears. I think it’s a little of both.

5. “I’ve Just Seen The Rock Of Ages” by Ralph Stanley and The Clinch Mountain Boys

I’ll admit; this is kind of another Keith Whitley song. I discovered it when looking into his history with The Clinch Mountain Boys, and he does sing lead on it, but Ralph Stanley comes in for the chorus and sang it many times after Whitley left the band.

The song is from the perspective of someone standing next to their mother’s death bed. The person hears their mother speaking on the biblical things she’s seeing as she dies.

Religious or not; this song will get you teary eyed. The lyrics are accompanied by a wonderful bluegrass backing track, and feature Whitley’s impeccable, more underrated, bluegrass-style delivery, alongside Ralph Stanley’s haunting croon for the chorus.

When I first heard it, I just listened like it was any old bluegrass tune and enjoyed it, but when I started really noting the lyrics, I was foggy eyed and immediately added it to my playlist. I also went as far as purchasing a vinyl record with the song on it.

Thanks as always for reading! I hope you enjoyed this list! Tell me what you think of the songs here, and if you’d like to see a third list! Leave some of your favorite underrated sad country songs as well!



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