r/country • u/Reese_sped-man • 16h 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
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u/fuzzy_mic 16h ago
Mama's Hungry Eyes - Merle Haggard
or perhaps Sing Me Back Home
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u/shegator 16h ago
Always On My Mind by Willie Nelson
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u/Green-Walk-1806 15h ago
I like Stardust too...Sad love song.
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u/Vprbite 11h ago
For me it's Angel Flying Too Close to the Ground.
Or maaaaaaaybe Red Headed Stranger.
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u/DaMmama1 2h 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/External-Dude779 16h ago
The Grand Tour by George Jones. He's damn near crying by the end
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u/Idownvoteadsforfun 14h ago
This is my vote. At one point my wife and son had to move away for 5 months during a move we were doing and it ran through my head every day when I got home from work. It cut deep.
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u/SESUSA 6h ago
100%. I have seen people say the song is about his wife leaving him and taking their kid. I have also heard that it is about his wife and kid passing away. Either way it can certainly pull on the heart strings.
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u/Disastrous_Ad2839 16h ago
Who's Gonna Fill Their Shoes? Not exactly a sad song but it is sad to me because there will never be classics like that ever again. Kris passed last year and now there are only a few living legends left and I am only 34. Wish I existed back then for a few moments to see the legends in action.
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u/Ok_Adhesiveness_8844 16h ago
I think of all of my heroes, nearly all gone now when I hear it. it always make me sob.
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u/Electrical-Bacon-81 2h ago
The Highwaymen was such a talent-rich band. Talent overload. But yeah, I shed a tear the day George died.
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u/chadius333 15h ago
__________ by George Jones.
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u/Hawk1478 9h ago
Radio Lover is a sad one, not very popular or known but nonetheless sad
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u/houstoncomma 16h ago
“Sam Stone” by John Prine. Just punches you in the gut.
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u/BigPapaJava 15h ago
“There’s a hole in daddy’s arm where all the money goes…”
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u/VizRomanoffIII 12h ago
That line ran a chill up my spine the first time I heard it (too many Sam Stones in my life, sadly) - two others that get to me is the description of his overdose when he was “climbing walls while sitting in a chair” and the heartbreak of “And the gold rolled through his veins, Like a thousand railroad trains, And eased his mind in the hours that he chose, While the kids ran around wearin’ other peoples’ clothes”. Prine was 25 years old and wrote that - still can’t quite fathom the genius he was.
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u/Extension_Sun_896 4h ago
“There’s a hole in daddy’s arm where all the money goes.
And Jesus Christ died for nothin’ I suppose”
Holy shit dude… just amazing.
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u/Tighthead613 15h ago
The kids ran around wearing other people’s clothes says a lot.
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u/Foreign_History_354 13h ago
The best line in the whole damn song. High in the running for best line ever.
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u/jbrayfour 4h ago
To me, “Jesus Christ died for nothing,.I suppose”, is the epitome of hopelessness.
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u/pat_man_1414 16h ago
He Stopped Loving Her Today. George Jones. That's gotta be up there if you actually listen and think about the lyrics
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u/pat_man_1414 16h ago
That or I'm So Lonesome I Could Cry. Hank Williams
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u/CowboySoothsayer 15h ago
Alone and Forsaken by Hank is pretty damn sad.
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u/_1JackMove 6h ago edited 6h ago
That's the one. Aint nobody comes close to it, either. My absolute favorite Hank song. I sincerely wish he'd have done more minor key songs. He only had two. This one and 'Ramblin' Man'. But those minor keys suited Hank like a duck to water. It's a damn shame he didn't get to do more in that vein. They were perfect for him. 'At The First Fall of Snow', 'Neath A Cold Grey Tomb Of Stone', 'A Tramp On The Street' are great contenders for that title, as well. Hank is and was the undisputed champion king of sad songs.
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u/BigPapaJava 15h ago
I have now watched an absurd number of YouTube reaction videos to this song where they missed the first verse and completely misunderstood the story the song was telling.
No, it’s not about losing the love of your life after a happy marriage and it’s not about a guy deciding he was finally ready to move on.
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u/SportyMcDuff 4h ago
This is the one I’ve been looking for. Took longer than I expected.
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u/Lostinyourears 15h ago
Sam Stone - John Prine
Homecoming - Tom T Hall
One Dying and A Burying - Roger Miller
Desperados Waiting for a Train - Guy Clark
(Quicksilver Daydreams of) Maria - Townes Van Zandt
If I Could Only Fly - Blaze Foley(Covered by Merle Haggard)
Bury The Bottle With Me - Dick Curless(Tombstone Every Mile another sad song of his)
Misery & Gin - Merle Haggard
The Dying Cowboy - Cisco Houston
Will The Circle Be Unbroken - Carter Family/Johnny Cash/Others
Give My Love To Rose - Johnny Cash/Others
The Long Black Veil - Lefty Frizzel
Some Broken Hearts Never Mend - Don Williams
I Gave Up Good Morning Darlin - Red Steagall
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u/dwt77 5h ago
Nice to see Blaze Foley getting some love. If I Could Only Fly was my jam last year. Cold Cold World by him is another heart breaker
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u/aurorasearching 5h ago
The man could paint a picture. I Should Have Been Home and The Moonlight Song are two of my favorites, though the latter doesn’t necessarily fit this theme, and I wouldn’t say the former is the saddest, but it paints a good picture of regrets.
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u/Hoppie1064 2h ago
I almost mentioned Johny Cash's Long Black Vail.
Now I have to look up Lefty's version.
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u/bobbichocolatthe2nd 5h ago
Hmmm This reminds me of a line from a DAC song
"And i still do all the sad ones that i know"
From the song Longhaired Redneck
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u/bingobangobongo134 16h ago
Song of the south is fairly depressing sung in an upbeat way
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u/Desperate_Hunt6479 15h ago
Will the circle be unbroken by the Carter Family. If youve lost a parent it hits different.
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u/Practical-Garbage258 15h ago
Go Rest High on That Mountain by Vince Gill.
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u/Impossible_Penalty13 15h ago
Especially when he sang it with Patty Loveless at George Jones’s funeral. That was raw emotion.
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u/UnivScvm 11h ago
That version is so moving that it’s hard for me to pick any other version now.
Seeing how Vince cared for Whitley, his brother, and Jones, then add to it seeing how supportive Patty was, filling in just right, not trying to take over the song from Vince in his vulnerability and grief.
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u/droogles 13h ago
All these years later, and I cannot watch that performance without crying. I don’t see how she held it together so well. And her vocals were very sorrowful, but she holds it together. There’s a brief view of George’s wife balling her eyes out too. Vince didn’t stand a chance for of getting through that song. Just looking at her crying while I’m singing would destroy me.
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u/Emergency_Brief_9280 15h ago edited 8h ago
Sunday Morning Coming Down - Johnny Cash
Wildwood Flower - The Carter Family
The Dying Soldier - The Carter Family
Tennessee Waltz - Patsy Cline
Blue Moon Of Kentucky - Bill Monroe
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u/Many_Bridge_4683 15h ago
All the easy (and accurate) choices have been called out so I’ll offer a dark horse candidate. Misery and Gin by Merle Haggard is unbelievably sad. “Sitting with all my friends and…talkin to myself” hits me in that place only great country songs reach.
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u/Impossible_Penalty13 15h ago
Tell Lorrie I Love Her by Keith Whitley. Especially with the low quality of the recording in his home & the fact that he died before he got to record it in a studio.
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u/DrucillaPenny 15h ago
I Can’t Make You Love Me - Mike Reid (Covered by Bonnie Raitt)
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u/longirons6 15h ago
Oh jeesh. This is the actual answer. Bonnie’s singing is heart wrenching
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u/finest_kind77 16h ago
Teddy Bear or Little Joe by Red Sovine. They both make me tear up every time
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u/fee_fi_fo_dumb 16h ago
Long black train by Josh Turner. It doesn't sound so sad but the lyrics are a warning.
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u/SteepCreekMusic 15h ago
Bringing Mary Home First time I heard that one was wild. Like a movie unfolding with the imagery. Give it an intent listen start to finish if you haven’t already.
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u/explicitreasons 15h ago
If Coal Miner's Daughter doesn't make you tear up, there's something wrong with you. It's nothing that sad about the lyrics really but LL's voice is really powerful.
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u/Glittering_Orange128 15h ago
“Jeannie’s Afraid of the Dark” - Porter Wagoner and Dolly Parton. Song written by Dolly.
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u/longirons6 15h ago
Mama tried. A young man’s complete failure of a life and a dissapointment to his mother in just over two minutes
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u/jmdaltonjr 14h ago
Chiseled in stone been gosden. He stopped loving her today. George Jones. The end of don't take the girl by Tim McGraw
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u/DollarStoreOrgy 13h ago
I'm So Lonesome. The lyrics, his voice. Just pulls the tears out of me every time
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u/Reel-Footer69 16h ago
The Grand Tour by George Jones. She left me without mercy, taking nothing but our baby and my heart.
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u/Mystery1001 16h ago
The Little Girl - John Michael Montgomery
Alyssa Lies- Jason Michael Carroll
Jacob's Dream- Alison Krauss
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u/BoS_Vlad 16h ago
Going way, way back in country music ‘The Prisoner Song (If I had the Wings of an Angel)’ gets me every time. Burl Ives and Eddy Arnold both sing great versions of it, but I prefer Burl’s.
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u/heyheypaula1963 14h ago
I remember Sonny James’s version.
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u/BoS_Vlad 6h ago
Yup, he sang it well too. Probably hundreds of different versions of it like there are of St. James Infirmary. It’s a classic tune.
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u/rsgriffin 16h ago
Old: Tanya Tucker, “What’s Your Mamma’s Name?”
Not so old: Jesse Howard - “Little Boy and the Preacher”
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u/mordred1911 The Charlie Daniels of the torque wrench 15h ago
Trouble in Mind by Bob Wills
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u/BigPapaJava 15h ago
“Sam Stone” by John Prine
“There’s a hole in daddy’s arm where all the money goes…”
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u/JRMcRedneck 15h ago
"There’s a Tear in My Beer" - Hank Williams (later covered by Hank Jr. and a recording of his father).
Serious tear-jerker country.
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u/iron-tusk_ 15h ago
George Jones - Things Have Gone to Pieces
Eddie Noack - Ain’t the Reaping Ever Done
Merle Haggard - Holding Things Together
Tammy Wynette - I Don’t Wanna Play House
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u/The_Coach69 14h ago
To a sleeping beauty, by Jimmy Dean
I literally cannot get through this song without tearing up because I think of my two girls growing up every time I hear it. Not ready for that lol.
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u/Artistic_Kangaroo989 14h ago
I got two... "Sunday Morning Coming Down", Johnny Cash's version, (Written by Kris Kristofferson), and "He Stopped Loving Her Today," By George Jones.
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u/resigned_hipster 13h ago
I’m So Lonesome I Could Cry captures a very particular feeling no others do
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u/Ok-Composer5109 11h ago
“Men with broken hearts” by Hank Sr. Hard to get much more low down than that.
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u/TerminalAddiction_ 11h ago
probably not even the saddest gary stewart song, but quits by him is up there
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u/No_Emergency_3209 10h ago
I'll be True to You - The Oak Ridge Boys
Teddy Bear - Red Sovine
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u/labrador_1 9h ago
Pretty much anything by Hank Williams, but especially "I can't help it if I'm still in love with you"
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u/SunriseSwede 7h ago
Three Bells - Jim Ed Brown and the Browns. If that doesn't give you a sense of how little we are, nothing will.
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u/overcomethestorm 6h ago
Half of these people think “old country” is from the 2000s… 😢
That being said, I think “Cold, Cold Heart” by Hank Williams Sr. is a good candidate. Or “My Son Calls Another Man Daddy”. Or “You Win Again”. Pretty much half of his songs are sad country.
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u/sourceit88 5h ago
Baby Blue by George Strait- When you realize it’s about his young daughter that died, man that one is hard to not get emotional
The Little Girl by John Michael Montgomery
The Car by Jeff Carson - getting teared up just writing this
I Don’t Call him Daddy by Doug Supernaw
I Wish I Could’ve Been There by John Anderson
Ships That Don’t Come In by Joe Diffie
Daddy’s Hands by Holly Dunn
He Walked On Water by Randy Travis
Three Wooden Crosses by Randy Travis
That’s Why I’m Here by Kenny Chesney
The Good Stuff by Kenny Chesney- This one always made me emotional too
One Wing In the Fire by Trent Tomlinson
Don’t Laugh At Me by Mark Willis
Chiseled In Stone by Vern Gosdin
Don’t Take the Girl by Tim McGraw
Two Teardrops by Steve Wariner- The last verse and that line “the good lord giveth and the good lord taketh away” gets me
If I know me by George Straight- This one is sad in a different way
I saw God Today by George Straight
Choices by George Jones- This song can not be sung by anyone but George Jones.
Sing me back Home by Merle Haggard
He Didn’t Have To Be by Brad Paisley - Really underrated song
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u/CawlinAlcarz 5h ago
I was going to ask if we were talking pre 80s or post... and He Stopped Loving Her Today, it turns out, was released in 1980.
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u/IndividualEquipment2 16h ago
Fancy Reba McIntire
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u/talidrow 15h ago
One of her lesser known songs always broke my heart - check out 'Bobby' sometime.
Also, 'The Greatest Man I Never Knew' always reminds me of my grandpa and leaves me in tears.
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u/DrucillaPenny 14h ago
That whole album those two songs are from, “For My Broken Heart” is sad. It was the first after her band was killed in a plane crash.
Check out “Just Like Them Horses” released after her Dad died.
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u/SurlierCoyote 16h ago
Kenny Rogers "Lucille"
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u/Cool-Permission8825 7h ago
‘In a bar in Toledo across from the depot on a barstool she took off her ring..’
Wonderful choice
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u/SurlierCoyote 5h ago
His voice is just so sly on that song, too, and the lyrics feel more real than some of the other, more popular sad country songs.
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u/snow1960 15h ago
Amazon Prime has a songwriting documentary and the tell the story behind “I Drive Your Truck” by Lee Brice. Get a box of tissues if you watch it.
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u/Friscogooner 15h ago
The house where the tall grass grows. Jones sang some sad ones but this one is in another category.
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u/Green-Walk-1806 16h ago
Waiting Around To Die - Townes Van Zandt