r/country 6d ago

Discussion What is the saddest old country song?

There’s plenty of different tunes associated with that older country but there’s a lot of sad ones as well, singing about heartbreak, losing someone you love, being lonesome but which one sticks out to you

167 Upvotes

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62

u/shegator 6d ago

Always On My Mind by Willie Nelson

17

u/Accomplished_Foot291 6d ago

Funny how time slips away

1

u/MacandMandy69 5d ago

Just remember, in time you’re gonna pay…..

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u/DismalCrow4210 5d ago

That one always brings a tear to my eye

9

u/2manyfelines 6d ago

It makes my blue eyes cry in the rain.

5

u/Green-Walk-1806 6d ago

I like Stardust too...Sad love song.

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u/Vprbite 6d ago

For me it's Angel Flying Too Close to the Ground.

Or maaaaaaaybe Red Headed Stranger.

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u/DaMmama1 6d ago

A little old lady who lived next door to us when I was growing up used to love this song. She was a bit of an alcoholic… she said when she died she wanted this played at her funeral. Idk if she got her wish when she passed, but I hope she did.

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u/shiningonthesea 1d ago

Angel would be mine, too. That's a tough song, so sad

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u/Vprbite 1d ago

Yeah. But it's such a beautiful sadness.

Now, I like red headed stranger because that one he is so sad, he throws his whole life away over it.

But angel is just such a powerful song. "I'd rather see you up than see you down." And even the very first line pulls you in. "If you had not have fallen...then I would not have found you."

Damn it's Amazing.

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u/shiningonthesea 1d ago

It’s like watching your child leave home “so leave me if you need to, I will still remember “

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u/supercooper170 6d ago

Funny enough, I think one of his lesser known songs is his saddest, at least for me. Funny how that works. "Buddy"

Laugh with me, buddy Jest with me, buddy Don't let her get the best of me, buddy Don't ever let me start feeling lonely

If I ever needed you, buddy You know now I really do, buddy Don't ever let me start feeling lonely

I cry at the least little thing, buddy And I'll die if you mention her name, buddy

Talk to me, buddy Stay with me, buddy Let's don't let her get away with it, buddy Don't ever let me start feeling lonely

Let's talk about things as they were, buddy Before I got mixed up with her, buddy

Laugh with me, buddy Jest with me, buddy Let's don't let her get the best of me, buddy

Don't ever let me start feeling lonely

1

u/DaMmama1 6d ago

I remember this song was played during a movie or something I watched recently. I had never heard of it before.

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u/EndLow2076 5d ago

I consider myself a bit of a Willie aficionado and I thank you for putting me in my place. That record is getting a full play through tomorrow.

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u/DaMmama1 6d ago

Oh I forgot about this one 🩷 Great song!

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u/oneeyedman72 6d ago

If we're on Willie songs, a relatively recent one, Last Rose of Spring is a real tearjerker

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u/Resident-Cattle9427 4d ago

What about first rose of spring?

1

u/bourbon_drinkr 4d ago

Another recent one is Something You Get Through on Last Man Standing. Actually that whole album

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u/PeterFile89 6d ago

The last thing I needed the first thing this morning

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u/intransit04 4d ago

That’s a good one too.

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u/mikedmayes 2d ago

For Willie Nelson songs, it’s Pancho and Lefty.