Saddest Country Songs of All Time Part 1

Saddest Country Songs of All Time Part 1

No need for a useless preamble here. Let's get down to brass tacks of what actually matters. Here’s the ten saddest country songs ever:

1. Elephant- Jason Isbell 

“There's one thing that's real clear to me

No one dies with dignity

We just try to ignore the elephant somehow”

The saddest country song of all time is Elephant by Jason Isbell. This song is absolutely gut wrenching. It’s regarded as one of his best songs off his most prolific album ‘Southeastern’. A song about losing a friend to cancer and the time spent with that person trying to avoid “The Elephant” in the room. Heartbreaking. 

2. Whiskey Lullaby- Brad Paisley and Alison Krauss 

“We watched him drink his pain away

A little at a time

But he never could get drunk enough

To get her off his mind

Until the night”

Maybe the most obvious pick on this list, Whiskey Lullaby is as sad as it gets. A song about a man literally drinking himself to death over losing the woman he loves the most. THEN his former lover drinks HERSELF to death after mourning his death. Side note: I don’t know if Angels exist or not but if they do, I assume they sound like Alison Krauss when they sing. 

3. Concrete Angel- Martina McBride

“Bearing the burden

Of a secret storm

Sometimes she wishes she was

Never born”

I can hardly listen to this song, it’s almost too much to take. A song about a young girl who endures abuse at the hands of her own mother, while the abuse goes unreported but is questioned by teachers and neighbors. By the end of the song the young girl is killed by her mother. The young girl goes to heaven where she will be loved more than she was on earth. 

4. He Stopped Loving Her Today- George Jones 

“I went to see him just today, oh but I didn't see no tears

All dressed up to go away, first time I'd seen him 

smile in years”

This list could’ve consisted of only songs by ol Possum, (A Good Year for the Roses, Grand Tour, If Drinkin Don’t Kill Me, Choices, ect.) but I elected to keep this list to one song per artist. ‘He Stopped Loving Her Today’ was the unanimous selection. Regarded by many as the greatest country song ever, ‘He Stopped Loving Her Today’ tells the story of a man who loves a woman he lost so much, it wasn’t until his death he finally got over her. 

5. Don’t Close Your Eyes- Keith Whitley

“Maybe I've, been a fool, holding on all this time

Lying here in your arms, knowing he's in your mind

But I keep hoping someday, that you'll see the light

Let it be tonight and don't close your eyes”

One of the most prominent country artists of the 80’s, the Kentucky Blue Bird had his demons and you heard it in his voice. A man that died way too soon from alcohol poisoning - he didn’t just sing sad songs, he lived them.

6. Diamonds and Gasoline- Turnpike Troubadours 

“Lord I love you

I wish you only knew

Well I wish you had a clue

I wish you had a clue you know

But I'm stuck here in Tulsa

With my Oklahoma blues

With a pair of concrete shoes 

That got me sinking pretty low”

Goddamn, long live Turnpike... this may be a biased opinion because I miss Turnpike so damn much. This could also be some recency bias. If you’ve never been drunk and stoned at 3 in the morning hurting to this song, then your opinion is irrelevant. 

7. I’m So Lonesome I Could Cry- Hank Williams Sr. 

“The silence of a falling star

Lights up a purple sky

And as I wonder where you are

I'm so lonesome I could cry

Hillbilly Shakespeare, Luke the Drifter, The Singing Kid, whatever you want to call him there’s no denying Hank Williams excellence in such a short period of time. There’s no room for interpretation with this song, everyone knows what Hank means when he says “I’m so lonesome I could cry”. Simple, yet perfect.

8. Traveling Soldier- The Dixie Chicks 

“Crying all alone under the stands

Was the piccolo player in the marching band

And one name read and nobody really cared

But a pretty little girl with a bow in her hair”

First things first, it’s ‘The Dixie Chicks’ not ‘The Chicks’. If you have a problem with that, then please never read another one of my blogs again, I beg of you. This song is excellent and painfully sad. It tells the story of a young waitress who meets a shy young man about to be deployed to fight in a pointless war in Vietnam. The two keep in touch by writing letters until the young man is killed in combat. 

9. Waitin’ Around To Die- Townes Van Zandt

“Now I'm out of prison

I got me a friend at last

He don't drink or steal or cheat or lie

His name's Codeine

He's the nicest thing I've seen

Together we're gonna wait around and die”

One of the most tortured men in country music history was Townes Van Zandt. From a young age Townes was always a little bit off, so much so his parents forced him into shock therapy. This song tells a story of a man who witnesses his father beat his mother when he was a boy. Later on he meets a woman who just fucks him over. He then finds trouble with the law attempting to rob a man. At the end of the song, the man is released from prison and finds solace with narcotics and alcohol as he waits around to die. 

10. Misery and Gin- Merle Haggard

“Lookin' at the world through the bottom of a glass,

All I see is a man who's fading fast”

Can you really have a top 10 list of saddest country songs without the Hag? I don’t believe you can. This is one of Haggard’s many brilliant sad country pain songs. It’s a tale as old as time - just a heartbroken man sitting at a bar getting drunk and seemingly having a good time, but any fool can tell that honky tonk heaven “really makes ya feel like hell”.


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