Country music is full of sad or touching songs that are sure to bring on the waterworks the first few times you hear them. However, not every tear-jerker retains its punch with multiple listens. Songs that can break your heart over and over again are something special. They’re the ones that I either quickly skip or turn up louder, depending on who is around.
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The songs listed below come from different eras of country music’s long, tear-soaked history. The only thing they really have in common is that they make my eyeballs sweat every time I hear them.
[RELATED: 4 Classic Sad Country Songs from the 1970s]
1. “Old Shep” by Red Foley (1936)
Red Foley proved that not every sad country song has to be about the end of a romantic relationship. With “Old Shep,” he showed everyone that songs about losing a furry friend are just as heartbreaking. This is guaranteed to tug on anyone’s heartstrings. However, animal lovers who know the pain of losing a pet are in for a real dagger to the heart.
“Old Shep” is about a boy and his dog. They grow up together and, eventually, Shep gets old and goes blind. The vet suggests that the song’s protagonist put his friend down. He doesn’t have to, though, because Shep lays his head in his master’s lap and goes peacefully. The knowledge that Foley based the song on a dog he had that was poisoned by a neighbor makes this song so much sadder.
2. “The Grand Tour” by George Jones (1974)
“He Stopped Loving Her Today” is often hailed as the saddest country song ever recorded. I contend that it’s not even the saddest song George Jones recorded. That title, in my opinion, goes to “The Grand Tour.” It’s a beautiful and heartbreaking song that never fails to get me.
There are two ways to look at this song, and both of them are sad. On one hand, it could be a song about a man whose wife took their baby and left him. On the other hand, it makes more sense if it’s told from the perspective of a man whose wife died in childbirth. Either way, the pain Jones injects into his voice makes me wonder who is cutting onions every time it comes on.
3. “Where Do I Put Her Memory” by Charlie Pride (1979)
Charlie Pride is, at the same time, hailed as one of the greats and criminally underrated. His vocal cords were made of gold, and his delivery never failed. “Where Do I Put Her Memory” is a perfect example of how he could make you believe every word of a song.
This is right up there with “The Grand Tour” for me. On the surface, it’s about a man who is haunted by the memory of an ex. A closer listen to the first verse brings that into question, though. I’ve taken down all her pictures / I’ve cleaned out all her drawers, Pride sings in the song’s opening lines. Who would leave and not take their clothes and photos?
4. “Using Again” by Benjamin Tod (2017)
There’s a special kind of heartache that comes with falling off the wagon. There’s a feeling of failure. Worse than that, though, is the notion that you’ve let everyone who cares about you down. It’s storm shame and self-loathing. Benjamin Tod (Lost Dog Street Band) captures that tempest of emotions perfectly with this track from his 2017 solo album I Will Rise.
This is just one of many songs from Tod’s catalog that punches me in the gut every time I hear it. However, I know I’m not alone in that. I once saw him perform the song live during a solo acoustic portion of a Lost Dog show. When the song ended, he was met with a round of applause that almost covered the chorus of sniffles that came from the crowd of people who were alternating between clapping and wiping their eyes.
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