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June 19, 2005



"The Wexford Lullaby" makes me bawl. I think part of it has to do with what was happening in my life when I first heard it, but still, you don't get much more heart-squeezing than that.


I agree--Cat's in the Cradle has got to be on the top 10 most heart wrenching songs EVER. But for classic sad, how can one leave out Danny Boy?


I went to a funeral the other day, where they played Cher's "If I Could Turn Back Time." Now THAT was sad.

Rod Dreher

One can easily leave out "Danny Boy." Man, if I never heard that song again, it'd be too soon. There's a whole bunch of great songs that I've heard so often I can't bear them any longer. Van Morrison's "Brown Eyed Girl," for one.

Playing Cher at a funeral is sad, but not necessarily for the reason the deejay thinks.

Here's a really, really sad song: "Family Reserve" by Lyle Lovett, a mournful ballad about how no family is strong enough to conquer death.


The Irish have the world's saddest songs. Ever notice how even supposedly happy Irish songs--like drinking songs--are so often about death?

My favorite sad Irish song: "Young Bridget O'Malley."


David Hecht

Hmmm...since we haven't hit one of the genres that seems to epitomize sadness--folk--I'll contribute a couple, both by Al Stewart, a modern folkie:

1. "Old Admirals" (http://rylibweb.man.ac.uk/data1/sy/jch/alwords/als40.htm), which is about growing old and unwanted, and,

2. "The Dark and the Rolling Sea" (http://rylibweb.man.ac.uk/data1/sy/jch/alwords/als54.htm), which is (among other things) about friendship betrayed.

James Freeman

I think what Barbara implies about the music you fill your house with oversimplifies the whole cause/effect thing. Sometimes, the dark music young people listen to isn't the cause of darkness in their souls, it's the coping mechanism after darkness already has intruded into their lives.

Back in the day, when I was 17 and 18, my "anthem" was "Badlands" by Bruce Springsteen. Now, for some kids, it's Korn screaming "F*** that s***."

Same sentiment, just expressed, more or less artfully, depending on one's perspective. My perspective leans heavily toward The Boss.

Now, turning to the saddest song, I'm surprised no one has mentioned "I'll Be Home for Christmas." In contemporary times, this is one of the most horribly, criminally misinterpreted songs of all times -- surely, one of the Vatican's "almost nonexistent" cases where capital punishment is acceptible would involve anyone guilty of performing an upbeat arrangement of this song.

Put back into its original context and meaning -- dig up a a World War II performance of this on, say, "Command Performance" -- "I'll Be Home for Christmas" is capable of reducing grown men to blubbering blobs of goo.


I'll Be Home For Christmas is horribly sad and should never be played in public ever again.


Eric Bogle wrote two of the saddest songs I've ever heard. The first was "And the Band Played Waltzing Mathilda" about Gallipoli (he was awarded "the Order of Australia" for his furtherance of the music of Australia).

The other is "William McBride" (apparently also called "No Man's Land" or "The Green Fields of France"). The chorus of this one goes:
Did they beat the drum slowly?
Did they sound the fife lowly?
Did the rifles fire o'er ye as they lowered you down?
Did the bugles sing 'The Last Post' in chorus?
Did the pipes play 'The Flowers o' the Forest'?

Sad, sad, sad.


Seasons in the sun is of course nothing but the poor English version of Jacques Brel's (nr two on most people's list of famous Belgians)song Le Moribond, which I think is really good, and pretty funny for a deathbed song. Check it out here: http://www.paroles.net/chansons/18746.htm


The Eagles' "Please Come Home For Christmas" always made me cry when it came out around 1979 or so:

So won't you tell me you'll never more roam
Christmas and New Years will find you home
There'll be no more sorrow no grief and pain
And I'll be happy, happy once again


I know it is over the top, but my kids and I cry when we hear this. They are very nice to me for a few hours after they hear it thouguh!

The Christmas Shoes

It was almost Christmas time, there I stood in another line
Tryin' to buy that last gift or two, not really in the Christmas mood
Standing right in front of me was a little boy waiting anxiously
Pacing 'round like little boys do
And in his hands he held a pair of shoes

His clothes were worn and old, he was dirty from head to toe
And when it came his time to pay
I couldn't believe what I heard him say

Sir, I want to buy these shoes for my Mama, please
It's Christmas Eve and these shoes are just her size
Could you hurry, sir, Daddy says there's not much time
You see she's been sick for quite a while
And I know these shoes would make her smile
And I want her to look beautiful if Mama meets Jesus tonight

He counted pennies for what seemed like years
Then the cashier said, "Son, there's not enough here"
He searched his pockets frantically
Then he turned and he looked at me
He said Mama made Christmas good at our house
Though most years she just did without
Tell me Sir, what am I going to do,
Somehow I've got to buy her these Christmas shoes

So I laid the money down, I just had to help him out
I'll never forget the look on his face when he said
Mama's gonna look so great

Sir, I want to buy these shoes for my Mama, please
It's Christmas Eve and these shoes are just her size
Could you hurry, sir, Daddy says there's not much time
You see she's been sick for quite a while
And I know these shoes would make her smile
And I want her to look beautiful if Mama meets Jesus tonight

I knew I'd caught a glimpse of heaven's love
As he thanked me and ran out
I knew that God had sent that little boy
To remind me just what Christmas is all about

Repeat Chorus


Gotta agree with 'noe' about "And the Band Played Waltzing Matilda" - down here Down Under that song tugs as many heart strings in NZ as it does in Oz - and another song from that terrible WW1 campaign, "Suvla Bay" .

Trouble is with sad songs - especially those from decades ago - you don't recall them until you hear them played, and then the eyes well..

But the Irish certainly have a nack of wrenching the heart with that lovely-sad lilting Celtic music bred by their history of oppression in past centuries..... a bit like the Jews, I guess, who also have some sad stuff.


I agree with "Cat's in the Cradle" has to be one of the saddest songs around. I remember when it first came out, I commented about it being so sad to my college roommate, a music major. She had only picked up the upbeat tune, and ignored the words totally.


In support of what James F. and Radactrice said about "I'll be Home for Christmas" --

My mom told me that the song was not allowed to be played for servicemen during WWII because they thought it would ruin morale.


A magnificent topic.

The Irish have the world's saddest songs. Ever notice how even supposedly happy Irish songs--like drinking songs--are so often about death?

Yes, and noe--I agree with you about Willie McBride. Completing the Irish trio for me would have to be "Boolavogue" and "The Croppy Boy." Ronan Tynan's version of "Isle of Hope" that opened the September 11 memorial laid me out as well. There are so many Irish songs like this--where the beauty and gut-wrenching sadness are intertwined.

"I brought my father with me" by Michael Smith (an Irish-American) would also top my list.

"For Real" by Bob Franke

"Further In" by Greg Brown--try to listen to this without losing it.


Like many great songs the lyrics are a bit flat on the page--you have to hear the searing music to this to fully appreciate it--but still..

I brought my father with me
I hope that you don't mind
I couldn't find it in me
To make him stay behind
Tonight the snow has fallen
The trees are white & cold
Their heavy branches bending
Can we come in from the cold?

I brought my father with me
Though it's been many years
Since he'd go down to Dolan's
For a shot & a couple of beers
When he'd take me with him
And he'd buy me a coke
It surely made my day
Now I take my father with me
Turnabout's fair play

Car trips to Pennsylvania
When all of us would sing
He sang Bells of St. Mary's
And he sounded just like Bing
Summer days down at the shore
Remembering how he
Would bless himself with foam before
He'd dive into the sea

There are some ways I'm just like him
Some ways he was just like me
And sometimes when the mirror's dim
His face is clear to see
Tonight the winds of heaven
Blow the stars across the sky
I brought my father with me
I couldn't say goodbye


This is my last post on this topic, I promise.

With reference to the Michael Smith and Greg Brown songs above--I'm reminded of a story I heard the Irish writer John O'Donoghue tell at a lecture several years ago. When asked to describe heaven, the questioned man (I can't remember who O'Donaghue was talking about) said: "Heaven means that I will see my mother and father again."



What about Barry Manilow's "Copacabana"? That one is pretty darn sad.

I also didn't recognize most of the songs on that list. But that Christmas Shoes one... ugh! I've heard that one, all right.

In Jesu et Maria,


After her bachellorette party, Lillith returned to "Cheers", drunk, escorted by the (paid) male dancer to whom she (mistakenly)thought herself engaged:

"I'll never hear 'Shock The Monkey' again, without crying."

Steve Cavanaugh

I think the song "Killkelly" has to rate as one of the saddest songs ever; based on letters found in a family's attic in the DC area, it captures succinctly the heartbreak that is at the heart of many immigrant families' lives. My wife hates it when I play this song, because it makes us all cry. But the Irish seem to have a genius for capturing the perennial sadness of their history via song.


The problem with that list of sad songs was that they were not poignant, just sad. Maybe even pathetic. What a collection of stinkers.

For a more cheerful perspective, look up some of those dogs, like Honey, in Dave Barry's Book of Bad Songs. You'll never have to suffer through them again when they turn up on the supermarket Muzak. Your fellow shoppers may be wondering why you a laughing out loud while shopping alone, but you won't be suffering...


Don't know about half of them. I remember "The People who Died" from my early 80s new wave/punk era [I might have mildly looked the part externally, but I was and always will be pure middle class bourgeoise!] Comfortably Numb & the whole "Wall" was a 'good' depressing mental excursion. [No I have never done drugs.]

I suspect that half the author's criterion included considering that they were 'sad' as in pathetic, awfully written etc.


This one got me real bad recently:

My Dear Son, it is almost June,
I hope this letter catches up to you, and finds you well Its been dry but they’re calling for rain, And everything's the same ol’ same in Johnsonville Your stubborn 'ol Daddy ain’t said too much, But I’m sure you know he sends his love, And she goes on,
In a letter from home I hold it up and show my buddies, Like we ain’t scared and our boots ain’t muddy, and they all laugh,
Like there’s something funny bout’ the way I talk, When I say: "Mama sends her best y’all"
I fold it up an' put it in my shirt,
Pick up my gun an' get back to work
An' it keeps me driving me on,
Waiting on letters from home

My Dearest Love, its almost dawn
I’ve been lying here all night long wondering where you might be I saw your Mama and I showed her the ring Man on the television said something so I couldn’t sleep But I’ll be all right, I’m just missing you An' this is me kissing you XX’s and OO’s, In a letter from home I hold it up and show my buddies,
Like we ain’t scared and our boots ain’t muddy, and they all laugh,'Cause she calls me "Honey", but they take it hard,'Cause I don’t read the good parts I fold it up an' put it in my shirt, Pick up my gun an' get back to work An' it keeps me driving me on, Waiting on letters from home

Dear Son, I know I ain’t written, But sittin' here tonight, alone in the kitchen, it occurs to me, I might not have said, so I’ll say it now Son, you make me proud
I hold it up and show my buddies, Like we ain’t scared and our boots ain’t muddy, but no one laughs, 'Cause there ain’t nothing funny when a soldier cries An' I just wipe me eyes
I fold it up an' put it in my shirt, Pick up my gun an' get back to work An' it keeps me driving me on, Waiting on letters from home

You can hear the song here:



Okay, one more:

"I Got Tears In My Ears From Laying On My Back In My Bed, Crying Over You."


"Thorntree in the Garden" -- Bobby Whitlock's song which closes Layla by Derek and the Dominos.

"That's the Deal" --- Kathy Mattea,off The Innocent Years, also an album closer.


I have a good friend whose Father left his family when he was little and he never knew him and almost never talked about him; but one time when we were riding in the car, "Cat's in the Cradle" came on the radio and he turned it up and he said "This was my Father's favorite song". Every time I hear it now it just makes me ache thinking about him.

That, along with any Irish immigrant song, makes me bawl. I cried moving a few hours down the turnpike from where I grew up and was sad I could only see my family once a month; I can't even fathom the ache my ancestors got leaving home forever.


Agree about most Irish ballads and reels (grew up listening to them) and also "Waltzing Matilda" which always kills me. A contemporary song which I think is sad and a general statement about humanity is REM's "Everybody hurts".

Thought Bruce Springsteen's "Tunnel of Love" was pretty sad since it seemed most of the album's songs dealt with his realization that he had a bad/loveless marriage (remember when he married the up and coming Hollywood actress and they split soon after). Good tunes though, but kind of depressing.

Hey, anybody else notice that when you get to a 'certain' age (40s) most of your especially female acquaintances are on anti-depressants? Maybe there were just too many cheesy sad songs in the 70s and they linger with us or something.


I like what Chesterton says about the Irish:

From the great Gales of Ireland
Are the men that God made mad,
for all their wars are merry
And all their songs are sad.

-"Ballad of the White Horse"


Very few "sad" songs make me cry (I cry at beautiful things), but... Christmas Shoes definitely did it to me the first time I heard it. It is nonetheless one of the worst songs in the history of mankind.

One of the best "sad songs" I know of is "Happy Birthday John," which has been done a million times in a certain subset of contemporary indie music (Christian alt-country-roots/slowcore). I belive it was written by a fellow named Bonnie Prince Billy, but the version I'm familiar with is by Starflyer 59. The chorus is...

Happy Birthday John
Where has your sweetheart gone
She left today
With one week's pay
And the boy she calls your son

Okay. Maybe that's more depressing than "sad," but...


"The Irish have the world's saddest songs. Ever notice how even supposedly happy Irish songs--like drinking songs--are so often about death?"

Wasn't it Chesterton who wrote (in the Ballad of the White Horse, I think)

"For the Great Gauls of Ireland
are the ones that God made mad,
For all their wars are merry-
Yet all their songs are sad."

Another sad song is an old Protestant funeral hymn "Golden Bells."

"There's a land beyond the river
That they call the sweet forever
And we only reach its shores by fates decree

One by one we'll reach the portals
There to dwell with the immortals
When they ring the golden bells for you and me"


Oops- must read *all* posts before adding my own next time.

Dale Price

My late grandfather once said that Doris Day's "Sentimental Journey" caused his traincar-load of GIs to start sniffling and blubbering back in 1945.

For my part, Bob Carlisle's "Butterfly Kisses" always makes me excuse myself and leave the room. Two daughters, don't you know...


I find "Have Yourself a Merry Little Christmas" even sadder than "I'll Be Home for Christmas." Amy, was it you who posted about James Taylor's remake, which restored the original gloom?

Maybe it's also because I associate "Have Yourself ..." with Judy Garland and her self-desctruction.


Hmm. Folks have already mentioned Kilkelly, And the Band Played Waltzing Matilda, and Willy McBride.

Soooo...how about "There Were Roses"? True story -- two Northern Irish friends, one Catholic and one Protestant. The Protestant was killed by a bomb, then his Catholic friend was killed in retaliation. "And another eye for another eye, till everyone is blind."

Andy Stewart's "The Orphan's Wedding" is a whole Greek tragedy -- and another true story. Orphans marry, then find out they are brother and sister.

But filk, the folk music of science fiction fans, also has some real tearjerkers. (I have been known to perpetrate such myself.) The strange thing is that it's the space songs that are the saddest these days, even if they didn't start out being sad songs at all. Like "Harbors":

"And I have seen the harbor,
And the ships are proud and bold,
And the children born this morning
May already be too old."


What about "Father of Mine" by Everclear? It's about a son confronting the abusive father who walked out on him. It was wildly popular about 8 years ago.

Here is the chorus:
Daddy gave me a name
Daddy gave me a name
Then he walked away
Daddy gave me a name
Then he walked away
My daddy gave me a name

David Pearson

I've probably heard the live version of Springsteen's "The River," about his sister and brother-in-law's marriage -- the version with the long spoken intro about his father warning him that the Army would "make a man of you," and how he only didn't go to Vietnam because he failed the physical -- 1,000, 2,000 times ... and I've yet to get through it without going lumpy in the throat at "All the little things that used to seem so important/Mister, they just vanished right into the air/Now I just act like I don't remember/And Mary acts like she don't care"

The last stanza -- "Now them memories come back to haunt me/They haunt me like a curse/Is a dream a lie if it don't come true/Or is it something worse/That sends me down to the river, though I know the river is dry" -- is a joy wrecker every time. I love it.


No one has mentioned the black spirituals for some reason.

David Pearson

Sorry, but the saddest complicated-relationship-with-dad song belongs to Springsteen, too: "Independence Day." "Say goodbye, it's Independence Day/Papa, now I know the things you wanted that you could not say/So won't you just say goodbye, it's Independence Day/I swear I never meant to take those things away." Pass the damn kleenex. (The whole song is essentially a guilt-soaked apology for succeeding as a rock musician; his father was a bitter former bus driver who told him he'd never amount to anything playing in a rock and roll band. I guess you have to know that to find the song so affecting.)

David Pearson

Good point, Tim. If it's sung right, "Were You There (when they crucified my Lord)?" is a tear-jerker fer sure.


Saddest song: Tears in Heaven by Eric Clapton
It's about the death of his 4 year old son.

Honorable mention: I Still Can't Say Good-bye as sung by Chet Atkins (I don't know if he wrote it.)


Some of you guys need to brush up on the difference between sad and sentimental. "Cats in the Cradle?" Please. "Honey?" Bwa-ha-ha-ha-ha.

For real sadness, it's hard to top Nashville. "Mama Tried" pretty much tops 'em all.


No one beats Patty Griffin for sad songs, but hers are actually good.

Top of the World - about a bitter old widower reflecting with anguished regret how he under-appreciated his wife during their marriage ("I think I broke the wings off a little songbird...")

Makin' Pies - about a spinster who lost the love of her life during WWII, and now spends her days makin' pies at the bakery and nights typing for her parish priest ("you could cry, or die, or just make pies all day")

Mother of God - about a girl from a dysfunctional family who moves to Florida and lives the rest of her life in pain over the separation from her natural mother, but finds solace in the Virgin Mary. ("I live too many miles from the ocean; I'm getting older and I get up every morning, with my cup of coffee and I talk to the Mother of God.")

Patty's not a practicing Catholic but her music is chock-full of Catholic imagery and meditation. Check her out.

Dale Price

Oh, and "The Grand Tour" by George Jones, which is about a man deserted by his wife:

Step right up, come on in
If you'd like to take the grand tour
Of a lonely house that once was home sweet home
I have nothing here to sell you
Just some things that I will tell you
Some things I know will chill you to the bone

Over there sits the chair
Where she brang the paper to me
And sit down on my knee and whisper oh I love you
But now she's gone forever
And this old house will never be the same
Without the love love that we once knew

Straight ahead that's the bed
Where we lay and love together
And lord knows we had a good thing going here
See her picture on the table
Don't it look like she'd be able
Just to touch me and say good morning dear

There's her rings all her things
And her clothes are in the closet
Just like she left them when she tore my world apart

As you leave you'll see the nursery
Oh she left me without mercy
Taking nothing but our baby and my heart
Step right up, come on in

As with all things George Jones, it's the delivery that's the killer. Though Aaron Neville did an interesting cover of it a few years back that captured some, but not all, of the pain.

Dale Price

The "Honey" reference was tongue-in-cheek. Bobby Goldsboro....[shudder.]

Barry Manilow without the overweening machismo.

BTW, Ellyn's right--do buy the Barry book. Also gets the tear ducts going, but in delight. "Someone left my cake out in the rain..."

Paul Pfaffenberger

"Sad Lisa" and "Wild World" by Cat Stevens. Wild World was done up-tempo but takes on a real desperation when slowed down.

"Vincent" (Starry Starry Night) by Don McLean.

For the saddest of those mentioned above, Tears in Heaven and the Patty Griffin tunes.


Some of the pslams are quite sad songs.

Speaking of which, did anybody see the recent film, "The Saddest Music in the World"?

David R.

Don't forget "Concrete Angel" by Martina McBride. It's got to be right up there with the most depressing songs, including the Christmas Shoes.


Where have all the children gone?


"Escape is So Simple" -- Cowboy Junkies

The way you kissed me this morning
It told me that you soon would be going
You didn't even look in my eyes
When you said goodbye

And last night in your sleep you broke all the promises
That I knew you would never keep
Now I'm reading the letter which you placed on the dresser
And you're five hundred miles down the road

Escape is so simple
In a world where sunsets can be raced
But distance only looses the knife
The pattern of its scar
Can always be traced

Yeah, I remember when we said 'forever'
Was the craziest word that we knew
But I think that I like it much better than I do 'goodbye'

And I could sit here all evening and think of the reasons
Why you are not by my side
Instead I'll go to the kitchen, find a strong chair to sit in
And drink myself far, far away

Escape is so simple
In a world where sunsets can be raced
But distance only looses the knife
The pattern of its scar
Can always be traced


While we're in the musical Liebe-und-Tod vein, here are two sad ones from 19th century America :

1. "Gentle Annie", composed in 1856 by Stephen Foster.
2. "Long Time Ago", as arranged by Aaron Copland in his "Old American Songs". His arrangement was based on a 19th C. poem ( "Near The Lake" )by George Pope Morris.


The saddest song ever is a song I hear played on Fordham's WFUV on the Irish show on the weekend...and for the life of me, I can't find the artist or all the lyrics. This song makes me stop what I'm doing and weep, bringing it all back again. But here's the title, I think, and the chorus:

Right through the Gates of Heaven

Up the stairs, boys
running to the top
without a thought to slow or stop
Up the stairs boys on 9-11
And they kept on going right through the gates of heaven.

Tim Ferguson

"Daniel my Brother" generally chokes me up.

Loreena McKennitt has a musical version of Tennyson's "Lady of Shalott" that really brings out the heartrending sadness of unrequited love.


Another maudlin fave which probably fits the author's criteria (ie, a plain old bad song) is that 70s song "Alone Again" by Gilbert O Sullivan.

Maclin Horton

Tom Waits:

From Alice: "Flower's Grave", "No One Knows I'm Gone"

From Blood Money: "All The World is Green", "Lullaby" ("Nothing's ever yours to keep /
Close your eyes, go to sleep")

From Mule Variations: "Georgia Lee" (possibly the saddest of all)

From Swordfishtrombone: "Soldier's Things"

I ain't lyin, folks. Don't say I didn't warn you.


My vote goes for a song with no original lyrics. It's called "Ashokan Farewell" and was used as background music in Ken Burns' Civil War series.

It was most famously used in the series during the reading of Sullivan Ballou's last letter to his wife, Sarah.


This is certainly a cheery read on a Monday!

Maclin Horton

Amy, thanks for the Dan Seals note. I heard this a few times on the radio and thought it was a knockout but, not being that much of a country fan, could never remember the artist's name.

Among folk songs, I think "The Golden Vanity" ranks way up there.


The Harry Chapin song about the singing tailor who saves all his money for a big city debut, then gets stung by critics and only ever sings to himself after that--that one always makes me sad. Mr. Tanner is the name of it, I think.


One of the saddest songs I've heard is Sugar Mice by Marillion, a band from the UK. It's sung by a rock star father who realizes his alcoholism, drug addiction, and all-around irresponsible living have destroyed his marriage and his family.

"Daddy took a raincheck, your daddy took a raincheck

Ain't no one in here that's left to blame but me

Blame it on me, blame it on me"

The song also has one of the most beautiful guitar solos you'll ever hear.



Angels in Waiting Tammy Cochran's song about her two older brothers who died of Cystic Fibrosis.

Green Fields of France
~gah~ Poor Willy McBride ~sniff~

Sgt. McKenzie Joseph Kilna McKenzie from We Were Soldiers.
Last thoughts of a dying soldier.

Tom Kopff

I second the nomination of Kilkelly as the saddest song ever. I chanllenge anyone to listen to it and not break into tears. Another song that gets me every time is Marie Bellet's Ordinary Time, She is greatly under-appreciated. And Emmylou Harris singing 'Calling My Children Home' from her Live at the Ryman cd!

William Bloomfield

Good call on Ashokan Farewell as a non-lyrical sad song.

One that gets me is a song entitled "Paper and Pen." It's a bluegrass song song by Alicia Nugent.

Another great one is "Whiskey Lullabye" sung by Brad Paisley and Allison Krauss.

And don't forget classic Bluegrass murder ballads like "Banks of the Ohio" and "Down in the Willow Garden."


lmo, how about "Wonderful" by Everclear, for that matter? (I have the feeling that someone in that band had a father who walked out early - you know, just a wild guess).


"I Don't Wanna Play House" by Tammy Wynnette


I Don't Wanna Play House
(Billy Sherrill/Glenn Sutton)

Today I sat alone at the window
And I watched our little girl outside at play
With the little boy next door like so many times before
But something didn't seem quite right today

So I went outside to see what they were doing
And then the teardrops made my eyes grow dim
'Cause I heard him name a game and I hung my head in shame
When I heard our little girl say to him.

I don't wanna play house; I know it can't be fun
I've watched mommy and daddy
And if that's the way it's done
I don't wanna play house; It makes my mommy cry
'Cause when she played house
My daddy said good-bye.

I don't wanna play house; I know it can't be fun
I've watched mommy and daddy
And if that's the way it's done
I don't wanna play house; It makes my mommy cry
'Cause when she played house
My daddy said good-bye.

"Seasons in the sun is of course nothing but the poor English version of Jacques Brel's ... song Le Moribond"

Poor, yes. But Jacques Brel, unlike Terry Jacks, didn't have Link Wray backing him up.

Tom Hoopes

I've come late to this party ... but the two saddest songs of all times are

Lyle Lovett's "She's Already Made Up Her Mind" and
Randy Newman's "Sail Away"

for entirely different reasons ...


Darcy Farrow

Words & music by Steve Gillette and Tom Campbell

Where the Walker runs down to the Carson Valley plain,
There lived a maiden, Darcy Farrow was her name
The daughter of old Dundee and a fair one was she
And the sweetest flower that bloomed o’er the range.

Her voice was sweet as the sugar candy
Her touch was as soft as a bed of goose down.
Her eyes shone bright like the pretty lights
That shine in the night out of Yerington town.

She was courted by young Vandermeer
And quite handsome was he I am to hear
He brought her silver rings and lacy things
And she promised to wed before the snows fell that year.

But her pony did stumble and she did fall.
Her dyin’ touched on the heart of us all.
Young Vandy in his pain put a bullet to his brain
And we buried them together as the snows began to fall.

They sing of Darcy Farrow where the Truckee runs through
They sing of her beauty in Virginia City too.
At dusty Sundown to her name they drink a round
And to young Vandy whose love was true.

Maclin Horton

Lyle definitely has some good entries in this race. "Sail Away" is a great song but I never thought of it as sad in the brings-tears-to-your-eyes way--more like very dark humor.

For those who don't know the song, it's a sort of travel agent's pitch to soon-to-be-enslaved Africans, about how great life in America is going to be: "Ain't no lions and tigers, ain't no mamba snake / Just the sweet watermelon and the buckwheat cake."

Tom Hoopes

Yes, he does it with his cynical humor, but it's a song about longing to "Sail Away ... across the mighty ocean into Charleston Bay."

A longing for America ... which is answered with slavery.

It's sad precisely because it catches you off guard.

Oh, and I meant to say saddest of OUR times. Saddest of all times would be the Psalm 137. "By the rivers of Babylon ..."

Mark R

Sad...or sappy?



Good call on "Ashokan Farewell." It was written by Jay Unger, who lives in the Catskills near me. A few years ago, he came to our high school and performed "Ashokan Farewell" on his fiddle with our high school band. Since then, the band plays it as the last song in their final concert of the year, as the band director's (who is loved by all the kids) way of saying good-bye to her seniors. We all cry every time!


Wonderful by Everclear
I don't wanna hear you say
That I will understand someday
No, no, no, no
I don't wanna hear you say
You both have grown in a different way
No, no, no, no
I don't wanna meet your friends
And I don't wanna start over again
I just want my life to be the same
Just like it used to be

Sonetka: Yeah, Everclear's lyrics beat a thousand blog posts on the disintegration of the American family.

Here's the bridge (if that's the correct term) to "Father of Mine". This is the part that always makes me cry.

I will never be safe
I will never be sane
I will always be weird inside
I will always be lame
Now I'm a grown man
with a child of my own
and I swear that I'm not going to let her know
all the pain I have known


First Christmas Away From Home

* Stan Rogers)

This day a year ago he was rolling in the snow
With a younger brother in his father's yard
Christmas break, a time for touching home
The heart of all he's known, leaving was so hard
Now three thousand miles away he's working Christmas Day
Earning double time for the minding of the store
He always said he'd make it on his own
He's spending Christmas Eve alone
First Christmas away from home

She's standing by the railway station, panhandling for change
One more dollar buys a decent room and a meal
Looks like the Sally Ann place after all
The vast and dreaming hall that echoes like a tomb
But it's warm and clean and free, there are worse places to be
And at least it means no beating from her dad
And if she cries because it's Christmas Day
She hopes it doesn't show
First Christmas away from home

In the hall they've got the biggest tree but it looks so small and bare
Not like it was meant to be
And the angel on the top it's not the same old silver star
You once made for your own
First Christmas away from home

In the morning there are prayers, then there's tea and crafts downstairs
Then another meal up in his little room
Hoping that the boys will think to call
Before the day is done, well it's best they do it soon
When the old girl passed away he fell apart more every day
Each had always kept the other pretty well
But the boys agreed the nursing home was best
'Cause he couldn't live alone
First Christmas away from home
In the common room they've got the biggest tree, it's huge and lifeless
Not like it was meant to be
The Santa Claus on top it's not the same old silver star
You once made for your own
First Christmas away from home


Tom Kopff: "Ordinary Time" - moving yes, but sad? It's about a woman happy with her ordinary life, no?


Tamarack, a Canadian folk group has some pretty sad but beautifully haunting songs...
"Lonesome Cowboy's Lament" and "Pamela" to name but two. Also, what about most of Patsy Cline's music?

Tom Hoopes

"September Song" (It's a long long way, from May to September ...)

"Sugar Mountain" by Neil Young

And, heck, any song about lost innocence and/or about September:

"Do You Remember" (... the kind of September ...)

"Night Moves" by Bob Seeger ... despite its obvious moral issues (or through them?) ... is a VERY sad song.


Sad song. Here's the one that literally caused tears and door slamming seconds ago as I sat reading this thread": it was -- "I Had a Little Chicken" -- the one who wouldn't lay an egg. It was the tune that came blaring from the speaker of the ice cream truck as it passed my house, and my "no way" didn't go over well nor did the reminder that we JUST got back from a birthday party.


Re: all the folks who think they're sappy songs

One of the most humbling things that a songwriter or performer finds out is this: a song and a singer don't have to be particularly good or touching to touch a hearer's heart. It's not us; it's something that works through us. The best anyone can do is work hard to be a good conduit.

"Taste" and "skill" and "song that works" are not necessarily the same thing. In fact, sometimes I worry that they're opposites! But the hard fact is, sometimes it's the banal sappy little song that catches a fragment of truth and feeling, and even beauty. Any songwriter who thinks there's no need to pay attention to those bright shards and figure out why they shine to other people is not a songwriter who's learning much.

Nobody knows what's going to say exactly what someone needs said for them. Nobody knows what song will stick, while other songs are forgotten. People in this thread are telling us what songs worked for them. You may not like the lab results, but it's silly and useless to ignore the data.

Still, I think most of the songs I've heard from among the ones folks have mentioned are pretty darned good songs.

Maclin Horton

"Darcy Farrow" is a great one, TSO. I was wondering who besides certain unfashionable '60s folkies had recorded it, checked AMG, and was surprised to see that Townes van Zandt did. I'll have to hear that.


This Irish folksong always gets to me:

"The Fields of Athenry

"By a lonely prison wall
I heard a young girl calling
Micheal they have taken you away
For you stole Trevelyn's corn
So the young might see the morn.
Now a prison ship lies waiting in the bay.

Low lie the Fields of Athenry
Where once we watched the small free birds fly.
Our love was on the wing we had dreams and songs to sing
It's so lonely 'round the Fields of Athenry.

By a lonely prison wall
I heard a young man calling
Nothing matters Mary when your free,
Against the Famine and the Crown
I rebelled they cut me down
Now you must raise our child with dignity..."

David Pearson

First time I heard Sarah McLachlan's "Angel," I was alone on a long stretch of empty highway late, late at night. Thought I might have to pull off to the side of the road and just bawl. Hahaha. You really can't separate the vocal performance from the lyrical content on a track like that; it's the /song/ that kills you. Springsteen's "Stolen Car" and "Cautious Man" are in this category, too.


Check out "Same Oul' Town" by the Saw Doctors. It positively rings with sadness.

David Pearson

OK, i'm thinking back now. The two best heartbreak-in-progress songs -- they'll rip your guts out if you've just been through a breakup, or if you remember what it was like to be there -- are Jackson Browne's "Late for the Sky" and Shawn Colvin's "Monopoly." I can't think of anything else that comes close to those two in that category. But, again, you can't separate the lyrical content from the performance. If you just read the lyrics without hearing the song, they ain't gonna lay a finger on you.


Ordinary Fool

Only a fool
Like fools before me
I always think with my heart

Only a fool
That same old story
Seems I was born for the part

It's a lesson to be learned
And a page I should have turned
I shouldn't cry
But I do
Like an Ordinary Fool
When her ordinary dream falls through

How many times
Have I mistaken
Good looks and laughs
For bad news

How many times
Have I mistaken
Good looks and laughs
For the blues

When a road I've walked before
Lands alone at my front door
I shouldn't cry
But I do
Like an ordinary fool
When her ordinary dreams fall through

Susan Y.

The song Kilkelly doesn't just make me cry, it makes me sob. I've seen it performed in public twice and both times I was afraid I was going to be asked to leave.

Another sad folk song: Barbara Allen. That's the kind of stuff I sang as a morose teenager, to the extreme annoyance of my family.

Tom mentioned Neil Young: The Needle and the Damage Done is sad, and also the best anti-drug song I know of, because it's short and non-preachy.

And now, my nomination for Saddest Song Ever, recorded by various Irish artists, the version here by the Voice Squad: I give you the immortal I Am Stretched on Your Grave.

I am stretched on your grave
And will lie there forever.
If your hands were in mine
I'd be sure we'd not sever.
My apple tree, my brightness,
It's time we were together,
For I smell of the earth
And am worn by the weather.

When my family thinks
That I'm safe in my bed,
From night until morning
I am stretched at your head.
Calling out to the air,
With tears hot and wild,
My grief for the girl
That I loved as a child.

Do you remember
The night we were lost
In the shade of the blackthorn
And the chill of the frost?
Oh, thanks be to Jesus,
We did what was right
And your maidenhead still
Is your pillar of light.

The priests and the friars
Approach me in dread,
Because I still love you,
My life, and you're dead.
I still would be your shelter
Through rain and through storm,
And with you in your cold grave
I cannot sleep warm.

So I'm stretched on your grave
And will lie there forever.
If you hands were in mine
I'd be sure we'd not sever.
My apple tree, my brightness,
It's time we were together,
For I smell of the earth
And am worn by the weather.

David Pearson

Remember the plaintive, a capella Scottish war-death song in the Mel Gibson movie "We Were Soldiers"? Sad. Powerful:



"Over the Rainbow" as sung by the late Eva Cassidy has to be one of the most hauntingly sad songs ever recorded.


The most depressing songs are "Seventeen" by Janis Ian and "Alone Again, Naturally" by Gilbert O'Sullivan.

The saddest song is "Try To Remember" (I think that's the name of it) from the musical The Fantastiks. I never thought of it as sad until I heard a thing on NPR about the production of The Fantastiks on Broadway and about when they finally re-opened after September 11, 2001. Imagine singing these lyrics again after the events of that day. Especially for those who lived in New York City.

Try to remember the kind of September
When life was slow and oh, so mellow.
Try to remember the kind of September
When grass was green and grain was yellow.
Try to remember the kind of September
When you were a tender and callow fellow.
Try to remember, and if you remember,
Then follow.

Try to remember when life was so tender
That no one wept except the willow.
Try to remember when life was so tender
That dreams were kept beside your pillow.
Try to remember when life was so tender
That love was an ember about to billow.
Try to remember, and if you remember,
Then follow.

Andrea Harris

"Bullet in the Gun (of Robert Ford)", by Elton John. This song always struck me as actually grieving (for a ruined relationship) rather than simply pleasantly melancholy. It was more the guitar effects, though, than the rather sappy words.

alias clio

So many I can think of; I'll stick to the ones not yet mentioned. (And by the way, the distinction is NOT between sad and sentimental, but between sad and self-pitying. Seasons in the Sun is bad in part because it's self-pitying. And then, its rhymes are BAAAAD.)

1. "Partons, la mer est belle" - about the drowning of some fishermen on a clear night.
The last line of the chorus goes, "je vois briller l'etoile qui guide les matelots." (My grandmother, whose first language was French, used to sing this at family gatherings, always reducing her large, burly, unsentimental sons to tears.) About grief at the hardships of daily life for most people most times and places...

2. Johnny We Hardly Knew Ye. (Why does everyone remember Danny Boy rather than this?). Grief for the destructiveness of war and violence.

3. A Scarborough Settler's Lament. ("Awa' wi' Canada's muddy creeks and Canada's fields of pine/Your land of wheat is a goodly land, but ah, it isna' mine")

4. The Trees They Grow High. Traditional song.

5. All My Trials. Traditional "spiritual", I think. From the islands. Consider the lines, "If religion were a thing that money could buy/You know the rich would live, and the poor would die/All my trials, Lord, soon be over."

6. The Jeannie C. (A Stan Rogers song - in the traditional mode.) "Come all ye lads, draw near to me/That I be not forsaken/This day was lost the Jeannie C./And my living has been taken/I'll go to sea no more."

7. For a song that inhabits the border land between self-pity and true sorrow, Emmylou Harris's "Boulder to Birmingham"..

8. Ditto for Van Morrison's "Madame George".

4. All My Trials. ("


Sad Irish songs:

She Moved Through the Fair
My love said to me
My mother won't mind
And me father won't slight you
For you lack of kind
Then she stepped away from me
And this she did say
It will not be long love
Till our wedding day

She stepped away from me
And she moved through the fair
And fondly I watched her
Move here and move there
And she went her way homeward
With on star awake
As the swans in the evening
Move over the lake

The people were saying
No two e'er were wed
But one has a sorrow
That never was said
And she smiled as she passed me
With her goods and her gear

And that was the last
That I saw of my dear

I dreamed last night
That my true love came in
So softly she entered
Her feet made no din
She came close beside me
And this she did say
It will not be long love
Till our wedding day

Would you believe my Kerry-born pastor sang this at an RCIA retreat one year, after a storm had killed the power? It was awesome.

My Youngest Son by Mary Black
My youngest son came home today
His friends marched with him all the way
The pipes and drum beat out the time
While in his box of polished pine
Like dead meat on a butcher's tray
My youngest son came home today

My youngest son was a fine young man
With a wife, a daughter and two sons
A man he would have lived and died
Till by a bullet sanctified
Now he's a saint or so they say
They brought their young saint home today

Above the narrow Belfast streets
An Irish sky looks down and weeps
At children's blood in gutters spilled
In dreams of freedom unfulfilled
As part of freedom's price to pay
My youngest son came home today

My youngest son came home today
His friends marched with him all the way
The pipe and drum beat out the time
While in his box of polished pine
Like dead meat on a butcher's tray
My youngest son came home today
And this time he'shome to stay


Sad mexican pop song. Sorry no translations, I know some of you speak Spanish.

Destino by Ana Gabriel
Pensar que el tiempo paso y ella nunca volvio,
dejo que el cielo se hiciera gris
por dentro el se murio como se muere una flor
y con la espera llego la edad y as murio

Con ilusiones marco su destino, pero no quiso escapar
nunca se supo por quien lloraba el nunca quiso hablar
hoy se preguntan con gran tristeza quien le arranco el corazon
quien se ha llevado con su partida todo el valor de amar, de amar.

Desde que solo quedo se le olvido sonrer
y ah en silencio espero, espero y asi murio


My nominee is "The Old House," recorded in the 1930s by John McCormack:

Lonely I wander through scenes of my childhood
They bring back to memory the happy days of yore
Gone are the old folk, the house stands deserted
No light in the window, no welcome at the door

Here’s where the children played games on the heather,
Here’s where they sailed their wee boats on the burn
Where are they now? Some are dead, some have wandered
No more to their home shall these children return

Lonely the house now, and lonely the moorland
The children have scattered, the old folk are gone
Why stand I here, like a ghost or a shadow?
’tis time I was movin’, ‘tis time I passed on.

James Freeman

Oh, and I meant to say saddest of OUR times. Saddest of all times would be the Psalm 137. "By the rivers of Babylon ..."

That would be, in popular-music annals, Rivers of Babylon by the Melodians, later covered by Boney M.

The song caused Psalm 137 to become my favorite of them all, particularly the King James version. Then again, the King James version of anything in the Bible sounds better by a bunch.


Much of the material by Townes Van Zandt (the late Texas singer/songwriter not one of the Skynerd boys)is pretty sad.

Like this one called Marie:

I stood in line and left my name
took about six hours or so
Well, the man just grinned like it was all a game
said they'd let me know
I put in my time till the Pocono line
shut down two years ago
I was staying at the mission till I met Marie
now I can't stay there no more

Fella 'cross town said he's lookin' for a man
to move some old cars around
maybe me and Marie could find a burned-out
van and do a little settlin' down
Aw, but I'm just dreamin', I ain't got no ride
and the junkyard's a pretty good ways
that job's about a half week old besides
it'd be gone now anyway

Unemployment said I got no more checks
and they showed me to the hall
my brother died in Georgia some time ago
I got no one left to call
Summer wasn't bad below the bridge
a little short on food that's all
Now I gotta get Marie some kind of coat
we're headed down into fall

I used to play the mouth harp pretty good
hustled up a little dough
but I got drunk and I woke up rolled
a couple of months ago
they got my harp and they got my dollar
them low life so and so's
harps cost money and I ain't got it
it's my own fault I suppose

The Pocono's down but the Chesapeak's runnin'
two freights everyday
if it was just me I'd be headed south
but Marie can't catch no train
She's got some pain and she thinks it's a baby,
says we gotta wait and see
in my heart I know it's a little boy
hope he don't end up like me

Well, the man's still grinnin' says he lost my file
I gotta stand in line again
I want to kill him but I just say no
I had enough of that line my friend
I head back to the bridge, its getting kinda cold
I'm feelin' too low down to lie
I guess I'll just tell Marie the truth
hope she don't break down and cry

Marie she didn't wake up this morning
she didn't even try
she just rolled over and went to heaven
my little boy safe inside
I laid them in the sun where somebody'd find them
caught a Chesapeak on the fly
Marie will know I'm headed south
so's to meet me by and by

Marie will know I'm headed south
so to meet me by and by

James Freeman

Re: Ashokan Farewell, the song itself is beautiful and haunting, but it is what was read over its strains in the first episode of Ken Burns' The Civil War that combined with it to reduce viewers to sobs:


July 14,1861
Camp Clark, Washington DC

Dear Sarah:

The indications are very strong that we shall move in a few days - perhaps tomorrow. And lest I should not be able to write you again I feel impelled to write a few lines that may fall under your eye when I am no more.

I have no misgivings about, or lack of confidence in the cause in which I am engaged, and my courage does not halt or falter. I know how American Civilization now leans upon the triumph of the government and how great a debt we owe to those who went before us through the blood and suffering of the Revolution. And I am willing - perfectly willing - to lay down all my joys in this life, to help maintain this government, and to pay that debt.

Sarah, my love for you is deathless, it seems to bind me with mighty cables that nothing but omnipotence can break; and yet my love of Country comes over me like a strong wind and bears me irresistibly with all those chains to the battlefield. The memory of all the blissful moments I have enjoyed with you come crowding over me, and I feel most deeply grateful to God and you, that I have enjoyed them for so long. And how hard it is for me to give them up and burn to ashes the hopes and future years, when, God willing, we might still have lived and loved together, and see our boys grown up to honorable manhood around us.

If I do not return, my dear Sarah, never forget how much I loved you, nor that when my last breath escapes me on the battle field, it will whisper your name...

Forgive my many faults, and the many pains I have caused you. How thoughtless, how foolish I have sometimes been!...

But, 0 Sarah, if the dead can come back to this earth and flit unseen around those they love, I shall always be with you, in the brightest day and in the darkest night... always, always. And when the soft breeze fans your cheek, it shall be my breath, or the cool air your throbbing temple, it shall be my spirit passing by.

Sarah do not mourn me dead; think I am gone and wait for me, for we shall meet again...


Sullivan Ballou was killed a week later at the First Battle of Bull Run (First Manassas to us Southerners).

frank sales

Saddest song for me is "Come to Me" from Les Miserables. First sung by dying Fantine when she entrusts Cosette to Jean Valjean and again by Cosette when Jean Valjean is dying. You'd have to have a heart of stone not to weep when you hear this sung during the play.

Maclin Horton

Talking Townes van Zandt, you can't really beat "Pancho and Lefty." And Emmylou Harris can make almost any song tug at your heart strings. Pretty much all of Wrecking Ball does that for me.

I'll second that Stan Rogers song, "The Jeannie C."

The poignancy of Janis Ian's "Seventeen" was tattered a bit for me by a reviewer who noted among her complaints that she was among the last picked when kids were choosing sides for basketball. The reviewer's unsympathetic rejoinder: "Face it, Janis: you're short."

Al DelG

Townes Van Zandt - yeah, "Marie" is one of the all time saddest, also "Caroline". Supposedly a woman asked Townes at a concert, "don't you play any happy songs?" - "Mam, these are happy songs!" May he rest in peace!

I'm surprised nobody yet mentioned John Prine -
"Sam Stone" and "Hello in There".


I've read somebody mention "Sgt. McKenzie" from "We Were Soldiers", but how come nobody mentioned that movie's ending theme, "Mansions of the Lord"? That was a pretty good "sad" song.

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