The Most Depressing Country Songs of All Time

This list (updated most recently in January 2008) is inspired by a 2005 article in The Guardian about the most depressing songs ever written, and mentions two — two! — country songs in the top fifteen (and one of those doesn’t count, because it’s Kenny Rogers). The other entry iross:

15. Maggie’s Dream Don Williams (1984)

Nashville may have a rich heritage of depressing music but this hemlock-gulping country weeper will force listeners to throw themselves into a vat of possum poo. Over a soporific music track, Williams sings about Maggie, a waitress who’s spent 30 years working at a diner and never had anyone to go home to. She plays the saddest songs on the diner’s jukebox while lamenting how she’s destined to die alone. It doesn’t help that Maggie is the size of a whale. We’re never told this but, hey, waitress, truck stop, platters of fried food? You work it out.

Ha! That’s not even the most depressing Don Williams song there is. Neither one even makes my Top 40 list, which follows.

It’s divided into four sections, each ranked separately, because so much of country music is apples and oranges, and I don’t think it’s fair to compare older stuff with newer stuff, or the stuff you hear on Clear Channel radio stations with the sort of stuff that can dissolve the paint off your car. And I don’t care what you think about Keith Urban, he’s not on this list. Nobody who’s managed to marry Nicole Kidman can ever, ever, ever complain about being depressed and unhappy. No. One. Period.

The Clear Channel Division

10. Martina McBride, “Concrete Angel:

Martina McBride has made something of a career out of stuff like this — “Broken Wing”, “Independence Day” — and I don’t blame her, not really. Everybody’s gotta eat. This one, though, this one will depress the living fool out of you. Here’s the ending:

A statue stands in a shaded place

An angel girl with an upturned face

A name is written on a polished rock

A broken heart that the world forgot

Through the wind and the rain

She stands hard as a stone

In a world that she can’t rise above

But her dreams give her wings

And she flies to a place where she’s loved

Concrete angel

The problem with this is not just the story, with the horrible, wretched child abuse going on, but that McBride’s soprano on this is just so lovely and uplifiting. The contrast is what kills me when I hear this; it’s wrenching.

9. John Michael Montgomery, “The Little Girl:

The bottom two on this list are about horrible things happening to children, and they’re lower-ranked because it’s just too easy to write about sick or abused kids in a depressing way. This one really ought to be lower, because it’s sentimental dreck of the worst sort — what the Snopes.com people call “glurge”, or what the Rascal Flatts people call “money in the bank”:

Her daddy drank all day and mommy did drugs

Never wanted to play

Or give kisses and hugs

So why is it more depressing than “Concrete Angel”? I think because it’s a worse song, but also because Montgomery does it in the worst way — depressed, monotonal, like someone’s making him eat vegetables.

8. Patty Loveless, “Nothin’ But the Wheel:

And forty-one goes on and on

And the lights go winding in the dawn

The sky’s the color now of polished steel

And the only thing I know for sure

Is if you don’t want me anymore

Then I’m holding on to nothin’ but the wheel

‘Scuse me just a second. I’ll be okay, no, really. Let’s just move on.

7. Alan Jackson, “Monday Morning Church:

It’s got one really awful rhyme in it:

And when I sit at your piano

I can almost hear those hymns

The keys are just collecting dust

But I can’t close the lid

Yeah, that’s not good. I like it, though, because it reminds me of that bit at the very end of the Johnny Cash video for “Hurt” (which we’ll talk about when we get to Johnny Cash in the next section), where he closes the lid on the piano, and smooths it with his hands, and then the screen goes dark and that’s the end, and we know Johnny’s about to die. Alan’s in a worse place; he can’t even close the lid, and that’s harsh.

6. Travis Tritt, “Best of Intentions:

Mostly on the list because of the video, which shows ol’ Travis in prison, which is pretty damned depressing and adds another layer to the meaning. “Anymore” could fit right here, too.

5. Kenny Chesney, “A Lot Of Things Different:

Chesney is the modern master of the bring-down, which is either very weird or very appropriate given his normal laid-back semi-Caribbean Jimmy Buffett wannabee style. There’s this, and “Who You’d Be Today”, which ought to be outlawed, and “The Good Stuff”, and “I Lost It”, and “That’s Why I’m Here”, which are all dark, powerful songs. This one, though, this one hurts:

She loved to be held and kissed and touched but I didn’t do it

Not nearly enough

Oh, and it gets worse:

And if I’d a known that dance was going to be our last dance

I’d a asked that band to play on and on on and on

I think we’d all do things a little different, there, Kenny. It’ll be all right. Really, it will. Say hi to Renee for me if you run into her again.

4. SheDaisy, “Come Home Soon:

Your standard ordinary country song about longing, but there’s a little twist to it; it’s about a military wife, so the missing husband isn’t just down at the Texas Showdown Saloon on nickel beer night, or even driving a truck out on the lonesome highway; he’s deployed in some Godforsaken outpost with people shooting at him. And — this is just incredible — on the album, it’s between “Passenger Seat” and “Don’t Worry ‘Bout A Thing”, which are happy-snappy-sappy upbeat songs about how good it is to be in a relationship and how things are going to be all right, respectively. What’s up with that?

3. Brad Paisley & Alison Krauss, “Whiskey Lullaby:

Brad Paisley isn’t the guy you count on for sad songs. Okay, there was “Who Needs Pictures”, which will make anyone rethink buying that digital camera. But he’s usually relentlessly upbeat and cheery and all that sort of crap. He and Alan Jackson did a cover of a Guy Clark song called “Out in the Parking Lot”, which is maybe the most cynical thing you ever heard in your life, and they made it sound like Six Flags on Friday night. This one, though, this one is world-class depressing, starting from the top:

She put him out

Like the burnin’ end

Of a midnight cigarette

That just lets you know, right off the bat, that you’re in for it. And then you get Alison Krauss in there, who has just the perfect voice for this sort of thing:

We laid her next to him beneath the willow

While the angels sang a whiskey lullaby

Come to think of it, I need a drink.

2. Trisha Yearwood, “The Song Remembers When:

There’s a lot of sad Tricia Yearwood songs. I could have put “On A Bus to St. Cloud” in there, or “Walkaway Joe”, or “Down on My Knees”, all good stuff. This one is high on my list because it’s meta-depressing; you can plug in any sad song you like and it’ll have whatever impact you want it to have:

I guess something must have happened

And we must have said goodbye

And my heart must have been broken

Though I can’t recall just why

The song remembers when

And that’s the problem with all these sad songs, isn’t it? You hit them at the right moment, and they will destroy you. Don’t think that they won’t.

1. Dusty Drake, “One Last Time:

The only one-hit wonder on the list, if you could even call this a hit. (Update:

This was written in December 2006. I just checked, and Dusty Drake has a charted single this summer, so he’s not a one-hit-wonder anymore, way to go.) It didn’t do any better than #36 on the country lists, and I believe that’s simply because it was just far too sad — and since it’s got a 9/11 theme on top of that, it’s really just piling it on. I mean, this makes the Alan Jackson 9/11 song sound like Natasha Bedingfield:

An’ she said:

“What about the plans we had?”

He said:

“This connection’s gettin’ bad.”

“Now c’mon baby, let me hear you smile,

One last time.”

I’m going to go put my wrist in a vise, douse myself with bourbon, and then set myself on fire.

The Legends Division

10. George Strait, “Let’s Fall To Pieces Together:

Great, great, great opening lines:

Pardon me, you left your tears on the jukebox

And I’m afraid they got mixed up with mine

It gets better after that — there’s sort of a happy ending — but damn, that’s a depressing way to start the song.

9. Conway Twitty, “Hello, Darlin’:

And if you should ever find

It in your heart

To forgive me

Come back darling

I’ll be waiting for you

That’ll keep you up nights, if you let it.

(Update: Having said that, they had a new Family Guy episode on the other day — new to me, anyway — and it concluded with three minutes of ol’ Conway singing “Hello, Darlin'” on the old Hee-Haw show or something like it, and he was wearing a pink shirt and a big ol’ toupee, and it looked like he needed dental work something awful. I can’t imagine anyone looking at that and saying, “Man, country music, I need to hear me some more of that.”)

8. Vern Gosdin, “Chiseled in Stone:

If you’ve never heard of Vern Gosdin, shame on you:

You don’t know about lonely,

Or how long nights can be,

Till you lived through the story

That’s still livin’ in me,

And you don’t know about sadness

’til you faced life alone,

You don’t know about lonely

’til it’s chiseled in stone.

This is one of those songs that’s so depressing that the protagonist goes home to his wife and gets over his depression — George Strait had one like that, called “I Hate Everything”, and there’s “The Good Stuff” by Kenny Chesney, referenced earlier. This is the best of this particular genre, mostly because Vern Gosdin sounds like he just ran over his foot with his lawnmower.

7. Willie Nelson, “Blue Eyes Cryin’ in the Rain:

Well, of course it’s on this list. If you don’t understand why, listen to the damn thing a couple more times, then come back to me.

6. David Allan Coe, “You Never Even Called Me By My Name:

The great Steve Goodman song, maybe the greatest country song ever written, but the rousing and defiant nature of the last chorus sort of makes it a bit less depressing than it might have been — that, and it’s so much a self-parody that it’s hard to get that depressed from listening to it. But the first stanza is as bleak as anything else out there:

Well it was all

That I could do

To keep from cryin’

That’s country, right there.

5. Hank Williams, “Cold, Cold Heart:

Could have picked any number of songs here – shoot, you could do a whole list that was just Hank Williams if you wanted to. I chose this one because it sort of defines what lugubrious is — sad, slow, a little whiny. You could make the argument that country music is so depressing because Hank Williams was so depressed.

4. Merle Haggard, “If We Make It Through December”:

Now I don’t mean to hate December

It’s meant to be the happy time of year

And why my little girl don’t understand

Why daddy can’t afford no Christmas here

Tough. Real tough. (And of course, this isn’t really child-related; it has more to do with the protagonist, trying hard to get by but not being able to put Christmas presents under the tree.) It could be #1, but it’s really a hopeful song, isn’t it? If you can just make it to January 1, we can quit this job and move south and start over again, maybe even California, and we’ll turn the corner somehow. Great stuff, this. You could have a lot more Merle Haggard songs on this list — like “I’m Always On A Mountain When I Fall”, which was featured in Brokeback Mountain (although it isn’t on the soundtrack for some weird reason) and was the only good C&W song used in the movie. But I’m not really sure about that. Merle’s persona is just too American, just too regular-Joe workingman for real true depression; even really tear-you-up songs like “Silver Wings” have a lilt to them that redeems them from the truly depressive.

3. Lefty Frizzell, “The Long Black Veil:

This is one of the songs that sparked this list:

She walks these hills

In a long black veil

She visits my grave

When the night winds wail

Heard this on the radio satellite o’ love the other day, driving down the road with my wife riding shotgun, and she changes the channel, because it’s too depressing. Well, of course it’s depressing, that’s kind of the point. What I did not know (thanks to Wikipedia) was that Dave Matthews covered it. I also did not know that the song was actually written by someone; I assumed it was a traditional song that Lefty just recorded.

2. Kris Kristofferson, “Sunday Morning Comin’ Down:

‘Nuff said.

1. Johnny Cash, “Give My Love to Rose:

Originally recorded on the Folsom Prison album, and then re-recorded on American IV, for which he won a well-deserved Grammy Award:

I found him by the railroad track this morning

I could see that he was nearly dead

I knelt down beside him and I listened

Just to hear the words the dying fellow said

And it just gets more and more pathetic. Good stuff. I could have put the famous cover of “Hurt” on here, too, maybe I should have, but this is the one that Johnny Cash wrote his ownself, and that deserves pride of place. You could put “Hurt” here at 1A and I wouldn’t mind.

George Jones Division

10. George Jones, “Choices:

This is George Jones on the flip side, looking back at a great career, and living with regrets in every syllable of every line. Drinking, missing shows, breaking up with Tammy Wynette, it’s all there. Great career, lots of #1 hits, the greatest country song ever recorded (#2 on this list, as you’ll see) and it’s all been for nothing. Just shoot me now.

9. George Jones, “She Thinks I Still Care:

Denial ain’t just a river in Egypt, baby. (The Anne Murray version may be even more depressing, because, you know, it’s Anne Murray.)

8. George Jones, “A Picture Of Me (Without You):

Nobody but the Possum gets away with crap like this:

Can you picture Heaven with no angels singing

Or a quiet Sunday morning with no church bells ringing

If you’ve watched as the heart of a child breaks in two

Then you’ve seen a picture of me without you

Lorrie Morgan did a cover version of this not too long ago, and it wasn’t half bad, but she should have known better. Nobody does this sort of stuff like George Jones.

7. George Jones, “A Good Year For The Roses:

Most of these songs are gosh-darn articulate about sadness or depression; this one isn’t quite. The protagonist here is so depressed he can’t even express it, just has to talk in platitudes about the rosebushes and the lawn and suchlike as his wife walks out on him. I will now strip all the skin off my back with an electric hedge trimmer.

6. George Jones, “If Drinkin’ Don’t Kill Me (Her Memory Will):

I’m actually surprised that more of these aren’t drinking songs, really. You could do separate lists for depressing drinking songs and depressing sober songs, and figure out which ones are worse. This one is maybe a little less depressing because it’s got the really comic image of Jones lying drunk in his car and getting woken up by the horn. This one is maybe a little more depressing because you know that it happened, probably more than once.

5. George Jones, “When The Grass Grows Over Me:

A prequel of sorts to our #2 song:

When you left I thought that I would soon be over you

Even told myself that I would find somebody new

Time and tears have come and gone but not your memory

But I’ll be over you when the grass grows over me

4. George Jones, “The Grand Tour:

The Aaron Neville version is almost as good, for that matter.

3. George Jones, “The Door:

To hear that sound

And to know its really over

Through tear stained eyes

I watched her walk away

And of earthquakes storms

And guns and war

Lord nothing has ever hurt me more

Than that lonely sound

The closing of

The door

I heard them interview ol’ George on the radio satellite o’ love a few months back, and he said he’s done concerts and shows around the world, and people yell out the songs they want to hear him play, and nobody, not even once, has said they want to hear this one, and that’s good enough for me.

2. George Jones, “He Stopped Loving Her Today:

Yes. Number two. I know, some people will want this to be number one, and I can’t help that. It’s just so awfully depressing:

Kept some letters by his bed

Dated 1962

He had underlined in red

Every single I love you

Gets me every time.

Maybe this ought to be Number One. Maybe it deserves to be Number One. But I have it at Number Two, and I’m sticking to my guns.

1. George Jones & Tammy Wynette, “Golden Ring :

I think this is the hands-down winner.

In a little wedding chapel later on that afternoon

An old upright piano plays that old familiar tune

Tears roll down her cheeks

And happy thoughts run through her head

As he whispers low, “With this ring, I thee wed.”

What’s depressing about that? Well, you have to listen to it, listen to the way Wynette and Jones make it sound all mopey and depressing — right up to the bar of “Here Comes The Bride” that plays over the lyrics, sad and tinny on that old upright piano. And of course, the couple break up, and the ring falls to the floor, and then back to the pawnshop it goes, for some other poor set of saps to pick out. And there’s the subtext; Jones and Wynette would marry and divorce in real life, as if you didn’t know.

Why is this more depressing than “He Stopped Loving Her Today”? The thing of it is, the character in that song is, at last, dead. His troubles are over. Depressing? Sure, but it’s like going to a funeral — you go, you’re sad, and then you go home and have a nice dinner and you get over it. A nasty divorce, on the other hand, sticks with you a long, long time.

Lone Star Division

These are all from the Texas roots-country division of C&W — stuff Clear Channel won’t play, so you might not have heard of it. I have it here because this is really a quantum leap in depressing over even George Jones. I mean, okay, the George Jones stuff is like, I dont know, Jack Daniels – strong Tennessee whiskey, a little raw going down, but still smooth. Some of the songs in this section, if you listen to them enough, will beat you over the head and take your wallet and dump your unconscious body in an alley down in Del Rio.

10. Gary Stewart, She’s Actin’ Single (I’m Drinkin’ Doubles):

Most of the rest of the songs in this section are more modern; this one isn’t, but it belongs here and nowhere else.

9. Lucinda Williams, Greenville:

Or, really, anything from Car Wheels On a Gravel Road – Lucinda Williams. I’m not picky. (It just as easily could have been “Minneapolis” or “Words Fell” from World Without Tears. (Update:

Or anything off West, including “Mama You Sweet”, which is the worst name ever for a depressing song.) And you can’t just read the lyrics, you have to listen to Lucinda sing the durn song:

Don’t wanna see you again or hold your hand

Cause you don’t really love me you’re not my man

You’re not my man oh you’re not my man

Go back to Greenville just go on back to Greenville

8. Robert Earl Keen, Blow You Away:

A lot of the songs on the list are pretty songs; this ain’t one of them:

The cops have stopped 10 miles of traffic

They’re sorry for all the delay

No need for alarm as they’re waving their arms

But they’d just as soon blow you away

And it goes on like this. What I think is depressing about this song is that it’s totally creepy and paranoid; what I think is really depressing about this song is that it may not be creepy and paranoid enough.

7. John Hiatt, Icy Blue Heart:

Actually, the Emmylou Harris version. “She came on to him like a slow moving cold front,” the song starts, and the metaphor just keeps getting stronger. Not the sort of thing you want to hear when it’s 28 degrees in Jersey.

6. Lyle Lovett, Promises:

Another one where the subtext is everything:

I offer no reason

I ask for no pity

I make no excuse

For the way that I am

And words are like poison

That sinks down inside you

And some things you do

You just don’t understand

It’s featured on the Dead Man Walking soundtrack; it’s from the perspective of the condemned man. Harsh stuff. (And it could just as easily have been anything else off of The Road to Ensenada, where it also appears, especially “Christmas Morning“.)

5. Guy Clark, “The Dark”:

A bit obscure; I couldn’t find lyrics online. But awful depressing, this is, about the dark, and how we’re all just walking around in it, maybe more than we know — in a dark so dark you can see Fort Worth from here.

4. James McMurtry, Holiday:

The highway patrolman

He stands in the rain

He just lets it run down to soften the stain

Of the blood on his pant leg

From working that wreck

And he won’t forget it

In time for the next holiday

I heard James do this song in Manhattan, in a little dive somewhere, right after Childish Things came out. The band was in between sets, so James just did this one by himself, just him and his guitar, and after awhile, he stopped playing, and did it spoken-word, and it was the spookiest thing you ever heard in your life. This one would depress the hell out of George Jones.

3. Terry Allen, “Queenie’s Song”:

Couldn’t find this online, either — Guy Clark’s version is on The Dark, where I heard it. Goes like this:

Some S.O.B. shot my dog

I found her under a tree

If I didn’t love that dog so much

It wouldn’t mean nothin’ to me

You son of a bitch

I’m gonna tell you what

I will not be deterred

I’ll find you out

And track you down

On that you got my word

Queenie’s getting buried

It’s time to dig the hole

New Year’s Day

In Santa Fe

Broke mean and it broke cold

If you don’t think that’s depressing, I’m coming to your house and letting all the air out of your tires and breaking all your shoelaces.

2. Townes Van Zandt, “Dublin Blues“:

I wish I was in Austin

In the Chili Parlour Bar

Drinkin’ Mad Dog Margaritas

And not carin’ where you are

Damn straight.

1. Slaid Cleaves, “Cold and Lonely“: (scroll down for lyrics)

Okay, maybe you never heard of Slaid Cleaves, but I mean, the man wrote the most depressing song of all time, you have to give him props.

Cold and lonely

I’m still on the farm

Cold and lonely

I never meant anybody harm

We lost children

It was too much for my wife

Cold and lonely

Living out a hopeless life

Cold and lonely

The winter hills were bare

Kathy’s crying

She’s got blood in her hair

Called the doctor

But the doctor says she’ll die

Cold and lonely

One more kiss goodbye

I mean, you take that, and some steel guitar, and… and… and… aw, hell.

It’s just depressing, that’s what it is.