I Revisited the Saddest Country Songs Ever Written—These 4 Still Bring Me To Tears

I am of the firm opinion that one cannot fully enjoy country music if they don’t like sad songs. It isn’t just that the genre is full of tear-jerking tunes. It’s that some of the best songwriting shows up in songs about loss and heartache. There’s something about pain that draws out the artistry in many writers’ pens.

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I have a long playlist of sad country songs that I go back to now and then. It contains some of the most powerfully sorrowful songs I could find. Most of those songs lose their punch after the first few listens, and they just become good tunes. The weepers below are different, though. They get me every time.

[RELATED: 4 Classic Sad Country Songs from the 1970s]

1. “Old Shep” by Red Foley

Red Foley co-wrote “Old Shep” with Willis Arthur and released it in 1936. Nine decades later, it is still one of the saddest country songs ever written.

I love horror movies and can watch all manner of terrible things happen to people and be fine. However, if a dog dies in a movie, I’m probably going to cry like a kid with a skinned knee. That’s only half of what makes “Old Shep” so heartbreaking. The other half is the sweet connection the song’s narrator has with his elderly pooch.

It doesn’t matter how many times I hear this song it’s an immediate skip if anyone else is around.

2. “Independence Day” by Martina McBride

I don’t know how or why Martina McBride’s “Independence Day” ends up in so many Fourth of July playlists and listicles. The only thing I can figure is that people just look at the title and go with it. However, this is the last song I want playing while I’m thinking about celebrating anything.

The song isn’t about celebrating freedom from British rule. It’s about a woman who is so badly abused that she chooses murder-suicide over living another day with the man who beats her and their child. That child, fortunately, was enjoying the county fair while her mother was freeing herself in the only way she knew how. This one ends with two dead bodies, a child in foster care, and countless listeners in tears.

3. “That Silver Haired Daddy of Mine” by Johnny Cash

This song, co-written by Jimmy Long and Gene Autry, is an old one. The Singing Cowboy released it in 1932, and it became his first hit. Since then, a long list of artists have covered it. There’s something about Johnny Cash’s cover that hits like a hammer to the heart, though.

The song is a two-and-a-half-minute apology from a man who has lived a rough life and knows he caused his father a lifetime of worry and heartache. Anyone who knows about Cash’s early life and career knows that he probably felt every word of this one when he was singing it. The addition of the piano and backing vocals makes this feel like a hymn, which makes it hit a little harder.

4. “He Stopped Loving Her Today” by George Jones

Look, I know. “He Stopped Loving Her Today” is on every list of sad country songs. But it’s here for the same reason that George Jones famously said, “Nobody’ll buy that morbid son of a b**ch,” when producer Billy Sherrill first brought it to him.

I would contend that this isn’t even Jones’ saddest song. In my mind, that honor goes to “The Grand Tour.” That being said, I can sing along to “The Grand Tour” without my voice cracking. I’ve heard this song no less than 100 times, and it gets me every time. At this point, my eyes start welling up after the opening lines because I know what’s coming.

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