25 Most Exquisitely Sad Songs in the Whole World

May 9, 2007 12:49 PM

The 25 most exquisitely sad songs in the whole world.(via I Will Dare)
posted by mr_crash_davis (357 comments total)

A Bee Gees song and no Tom Waits. Boo.
posted by quite unimportant at 12:59 PM on May 9, 2007 [3 favorites]

Gah, I already saw this. I have no idea what they are thinking. Mind you, I've never heard half of these songs, but the ones I have heard just aren't that sad -- I mean, Space Oddity?

And where are the Cowboy Junkies in that list?
posted by lupus_yonderboy at 12:59 PM on May 9, 2007

Bah.
posted by dilettante at 1:00 PM on May 9, 2007

Ugh, 25 clicks. Will a friendly person make a list?
posted by dgaicun at 1:01 PM on May 9, 2007

No Portishead either, those guys were sad
posted by zeoslap at 1:01 PM on May 9, 2007

Ha, finally the Pernice Brothers make #1 SOMEWHERE.

(I've always thought of that as one of their more uplifting songs...)
posted by unSane at 1:03 PM on May 9, 2007

I'm with dgaicun and lupus_yonderboy: already saw this and couldn't click through 25 pages. I like the idea fine, but not the layout.
posted by cgc373 at 1:04 PM on May 9, 2007

The list:

25. 'The River' - Bruce Springsteen (1980)
24. 'Nothing Compares 2 U' - Sinead O'Connor (1990)
23. 'No Surprises' - Radiohead (1997)
22. 'A Change Is Gonna Come' - Sam Cooke (1964)
21. 'Space Oddity' - David Bowie (1969)
20. 'That's the Way I've Always Heard It Should Be' - Carly Simon (1971)
19. 'Lost Cause' - Beck (2002)
18. 'I've Gotta Get a Message to You' - Bee Gees (1968)
17. 'Back to Black' - Amy Winehouse (2006)
16. 'Shilo' - Neil Diamond (1968)
15. 'My Mom' - Chocolate Genius (1998)
14. 'Anyone Who Had a Heart' - Dionne Warwick (1963)
13. 'Naked as We Came' - Iron & Wine (2004)
12. 'In the Wee Small Hours of the Morning' - Frank Sinatra (1954)
11. 'Brick' - Ben Folds Five (1997)
10. 'In the Real World' - Roy Orbison (1989)
9. 'Concrete Angel' - Martina McBride (2001)
8. 'Dance With My Father' - Luther Vandross (2003)
7. 'Hallelujah' - Jeff Buckley (1994)
6. 'He Stopped Loving Her Today' - George Jones (1980)
5. 'I Know It's Over' - The Smiths (1986)
4. 'Hurt' - Johnny Cash (2002)
3. 'Eleanor Rigby' - The Beatles (1966)
2. 'Gloomy Sunday' - Billie Holiday (1941)
1. 'Chicken Wire' - Pernice Brothers (1998)
posted by mr_crash_davis at 1:04 PM on May 9, 2007 [1 favorite]

Unspeakably poor list.
posted by tkchrist at 1:04 PM on May 9, 2007

I've never thought of Shilo as a sad song. It's about transcending sadness, by rocking out.
posted by Flashman at 1:04 PM on May 9, 2007

Space Oddity is sad, but the saddest song ever is The Pogues' "And the Band Played Waltzing Maltilda."

Reduces me to tears everytime (assuming everytime = the times there's been whisky drinking going on).
posted by notyou at 1:05 PM on May 9, 2007

And for that matter, why is it only pop music, nearly all in the last 10 years? Wagner has some of the most incredibly sad songs. "Strange Fruit" is an incredibly sad song. "Stardust" is sad. "Saint James Infirmary Blues" is very very sad.
posted by lupus_yonderboy at 1:06 PM on May 9, 2007

by the way, here's a vote for the Wrens' '13 Months in 6 Minutes'.
posted by unSane at 1:06 PM on May 9, 2007

I would have put "The River" at the top, not the bottom, personally. And where are "Angie" and "Wild Horses"?
posted by scratch at 1:06 PM on May 9, 2007

No "Cat's in the Cradle"

RIP: Dad, 2002
posted by winks007 at 1:06 PM on May 9, 2007 [4 favorites]

The Pernice Brothers get the #1 SADDEST SONG EVER IN THE ENTIRE WORLD???

Also, if it's in the whole world, why are they all in English?

Also, Iron and Wine doesn't count - he's trying way too hard to get ON a list like this.

Also, I can't believe Neutral Milk Hotel didn't make the list.

Also... no, that's all.
posted by ORthey at 1:06 PM on May 9, 2007

No Elliot Smith? w.t.f.
posted by ninjew at 1:07 PM on May 9, 2007 [1 favorite]

Oh, and where's "Shake Some Action" (F. Groovies) and "That's Entertainment" (the Jam).

I guess my favorite sad songs suck.
posted by scratch at 1:07 PM on May 9, 2007

One more also: Cat Stevens' Father & Son. Seriously.

How can I try to explain?
When I do, he turns away again
It's always been the same, same old story
From the moment I could talk
I was ordered to listen, now
There's a way and I know that I have to go

Chills, I tellsya!
posted by ORthey at 1:07 PM on May 9, 2007 [1 favorite]

'A Good Year For The Roses' is universally recognized by me to be the saddest song of all time.
posted by ND¢ at 1:08 PM on May 9, 2007 [1 favorite]

Surely, "The Killing of Georgie - Rod Stewart" would be in the top 25?
posted by winks007 at 1:08 PM on May 9, 2007

I'd have put Paul Simon's American Tune on the list.
posted by Miko at 1:09 PM on May 9, 2007

17. 'Back to Black' - Amy Winehouse (2006)

You've GOT to be kidding me.
posted by spicynuts at 1:09 PM on May 9, 2007 [1 favorite]

Wow, really weak list. It had hope near the top because Cash's Hurt cover and Eleanor Rigby deserve top slots, but there are way too many obvious omissions here.

How about:

Eric Clapton - "Tears in Heaven"
Moxy Fruvous - "Gulf War Song"
Cat Stevens - "Father & Son"
Warren Zevon - "The Wind," "Keep Me In Your Heart," "Don't Let Us Get Sick"

And of course, Harry Chapin - "Cat's in the Cradle." CAT'S IN THE FUCKING CRADLE wasn't on this list. That song should be Pavlovian at this point. You have to say the title in parts just so you don't tear up. It's like the crying version of the Monty Python "world's funniest joke" sketch.
posted by XQUZYPHYR at 1:11 PM on May 9, 2007 [9 favorites]

"Sometimes it Snows in April" by Prince

Sometimes it snows in April
Sometimes I feel so bad, so bad
Sometimes I wish that life was never ending,
But all good things, they say, never last

All good things they say, never last
And love, it isn't love until it's past

So sad I can't even listen to it anymore.
posted by triggerfinger at 1:11 PM on May 9, 2007

"Sixteen Straws" by The Drones.
posted by kid ichorous at 1:12 PM on May 9, 2007

Blah. What's sad is this list. And you have to click to see each one to boot.
posted by graymouser at 1:12 PM on May 9, 2007 [1 favorite]

No Patti Smith!
posted by lupus_yonderboy at 1:12 PM on May 9, 2007

Any random grouping of twenty-five Leonard Cohen songs beats this.

And yeah, the presence of Amy Winehouse destroyed any credibility that list gained by including 'The River'.
posted by Pastabagel at 1:13 PM on May 9, 2007 [1 favorite]

I vote for Willie Nelson's "Always on My Mind."
posted by inconsequentialist at 1:13 PM on May 9, 2007

No Elliot Smith? w.t.f.

Don't screw with the curve. This is just semi-professional sad we're talking here. For that olympic-level sad we'd need to dredge out Mozart's Requiem mass and Monteverdi and shit.
posted by kid ichorous at 1:16 PM on May 9, 2007 [2 favorites]

Patches, I'm depending on you, son, to pull the family through.
posted by box at 1:16 PM on May 9, 2007 [1 favorite]

More like, Amy Whinehouse!

Am I right, fellas???
posted by ORthey at 1:16 PM on May 9, 2007

Also, most people think "Happy Birthday" is pretty grim, at least once they turn 21.
posted by kid ichorous at 1:17 PM on May 9, 2007 [1 favorite]

'Big Dipper" by Cracker
'Good Feeling' by the Violent Femmes

And as pointed out above, a list of sad songs with no Willie Nelson on it is like a list of... well anything without Willie Nelson on it. Put him on all your lists. He's earned it.
posted by ND¢ at 1:20 PM on May 9, 2007

On a list of this quality, the top spot should've gone to "Christmas Shoes."
posted by booksandlibretti at 1:20 PM on May 9, 2007

Actually, if you click all the way through to the "Your Sad Songs", there's a song called "Alyssa Lies" that is notable only because the sad part of the song comes so totally out of nowhere that your reaction can only be to shake your head and utter "Jesus Christ!"
posted by Pastabagel at 1:21 PM on May 9, 2007

ARG, right, no Leonard Cohen!

Once there was a path
and a girl with chestnut hair,
and you passed the summers
picking all of the berries that grew there;
there were times she was a woman,
oh, there were times she was just a child,
and you held her in the shadows
where the raspberries grow wild.
And you climbed the twilight mountains
and you sang about the view,
and everywhere that you wandered
love seemed to go along with you.
That's a hard one to remember,
yes it makes you clench your fist.
And then the veins stand out like highways,
all along your wrist.
And yes it's come to this,
it's come to this,
and wasn't it a long way down,
wasn't it a strange way down?
posted by lupus_yonderboy at 1:21 PM on May 9, 2007 [1 favorite]

Technically, Jeff Buckley's cover of Cohen's Hallelujah is on the list, but still.
posted by Pastabagel at 1:23 PM on May 9, 2007

The Pogues cover of "And the Band Played Waltzing Matilda" is OK, but the June Tabor cover is considered to be the final word on that song by the original artist, Eric Bogle. Actually, Bogle's acoustic version, as can be heard here (mp3, very slow link at the moment, from this page) is more appealing than the Pogues cover...which isn't bad.
posted by maxwelton at 1:23 PM on May 9, 2007 [1 favorite]

Johnny Cash - Spritual
Low - Over the Ocean
U2 - MLK
posted by DieHipsterDie at 1:25 PM on May 9, 2007

Hmm. Only two songs before the 1960's. I guess people didn't get sad back in those days.

Kid ichorous, you are correct - Che Faro Senza Euridice is number 1, probably.
posted by QuietDesperation at 1:25 PM on May 9, 2007

The biggest flaw inherent in music criticism about the emotive process is exemplified perfectly by a list such as this: the overriding focus on lyrics.

It's in my own experiences that the most sullen, melancholic adventures arrive with instrumentation.

For example, here is ultimate dread, yearning, and triumph all rolled into one: the best track ever recorded.
posted by Mach3avelli at 1:26 PM on May 9, 2007 [2 favorites]

There's only one.

Anybody got a kleenex?
posted by Wolfdog at 1:27 PM on May 9, 2007 [1 favorite]

Actually, the *real* number 1 saddest song of all time wasn't printed just because you can't even say the title without falling into a blubbering mess of a sad blob. Here Comes a Regular by the Replacements. See, look at me. I'm sobbing like a recovering alcoholic after a three day bender. Which is appropriate, really.
posted by NoMich at 1:28 PM on May 9, 2007 [4 favorites]

* The Night that the Lights went out in Georgia
* American Pie - Don McLean
* Millie and Billy - Alice Cooper
* Down in a hole - Alice in Chains
* 24 Hours - Jem
* Chloe/Crown of Thorns - Mother Love bone
* Dallas 1pm - Saxon

Maybe we need our own list?
posted by winks007 at 1:29 PM on May 9, 2007

The readers' addenda cover some of the more egregious lacunae, including "Cat's in the Cradle." And for the record, the saddest song I've heard lately is "Kilkelly Ireland". The lyrics were based on a stash of letters the writer found, written to his great-grandfather by his great-great-grandfather across a span of over thirty years.
posted by Faint of Butt at 1:30 PM on May 9, 2007 [2 favorites]

One of those (arguably dickish) critical tics I have is with that Jeff Buckley version of Hallelujah. Any time anyone extolls that song, especially over Cale's superior cover, I immediately dismiss them as more concerned with histrionics than depth and unable to tell bathos from sentiment.
Yes, yes, you can like it; you're just wrong and have terrible taste.
posted by klangklangston at 1:32 PM on May 9, 2007 [3 favorites]

No mention of the Dion version of Abraham, Martin and John?!

Now I'm really sad.
posted by tittergrrl at 1:32 PM on May 9, 2007

"No Surprises" isn't even Radiohead's saddest song. That distinction clearly belongs to "Pyramid Song," which, as far as I can tell, was written about my cousin's suicide, and as such causes my throat to get knotty every time I hear it.
posted by saladin at 1:33 PM on May 9, 2007

"Hope" by Dirty Three?
posted by rush at 1:33 PM on May 9, 2007

aka 25 pages of ads & a list made in 20 minutes in order to get posted to digg.
posted by TheOnlyCoolTim at 1:34 PM on May 9, 2007

To add to what saladin said, "No Surprises" isn't even the saddest song on OK Computer.
posted by chimaera at 1:35 PM on May 9, 2007

I'm writing a song all about you
A true song, as real as my tears
But you've no need to fear it
'Cause no one will hear it
Sad songs and waltzes aren't selling this year
posted by ND¢ at 1:36 PM on May 9, 2007 [1 favorite]

"Waterloo Sunset", the Kinks

And maybe it's my Irish heritage getting the best of me, but no "Danny Boy"?
posted by maryh at 1:36 PM on May 9, 2007

Cat Power's "Love and Communication"?
posted by Dizzy at 1:36 PM on May 9, 2007

The saddest song ever written is "I Know" by Fiona Apple.
posted by facetious at 1:37 PM on May 9, 2007

No "I'm So Lonesome I Could Cry"? Seriously? (Preferably the Al Green cover, but the Johnny Cash/Nick Cave version isn't bad either.)
posted by Vervain at 1:39 PM on May 9, 2007

Lame, lame list - No Nick Drake, Elliott Smith, Joni Mitchell?

What is kitsch like Space Oddity, the Bee Gees, and (even though I love the beatles) Eleanor Rigby doing there?

Also, for future reference, the saddest song ever is These Cold Fingers, by Bill Morrissey
posted by JeffL at 1:40 PM on May 9, 2007

"Tuesday's Gone"
Lynyrd Skynyrd (1973)

The Breakdown: Saddest guitar part ever. Saddest piano part ever. A train song.

The Waterworks:
And I don't know where I'm going.
I just want to be left alone.
Well, when this train ends I'll try again,
But I'm leaving my woman at home.

Casualty Count: My baby.
posted by kirkaracha at 1:40 PM on May 9, 2007

greymouser hit the nail on the head.
posted by goml at 1:41 PM on May 9, 2007

Sad songs are nature's onions.
posted by Espy Gillespie at 1:42 PM on May 9, 2007 [1 favorite]

No Red House Painters?: Medicine Bottle, Uncle Joe to name a couple...
posted by elmono at 1:45 PM on May 9, 2007

and, just .... ewww
posted by goml at 1:46 PM on May 9, 2007

side 2 (songs 6-10 for you youngsters) of berlin by lou reed , guaranteed to ruin your day. from 'the bed':
This is the place where we used to live
I paid for it with love and blood
And these are the boxes that she kept on the shelf
Filled with her poetry and stuff

And this is the room where she took the razor
And cut her wrists that strange and fateful night
And I said, oh, oh, oh, oh, oh, oh, what a feeling...
posted by aquanaut at 1:46 PM on May 9, 2007

ditto on the Leonard Cohen. When I first saw the fpp headline, my initial reaction was "Leonard Cohen wrote them all"

Seriously, no Richard Thompson? "Al Bowly's In Heaven" and "Whithered and Died" should qualify.
posted by hwestiii at 1:47 PM on May 9, 2007

Trouble in Mind - Muddy Waters
Sunday Morning Coming Down - Johnny Cash
You Don't Miss Your Water - William Bell, Otis Redding, The Byrds
posted by otio at 1:50 PM on May 9, 2007

My personal #1 saddest is Nico's Frozen Warnings. If I had to pick between her original the solo piano/voice version John Cale delivers during the credits of the movie Nico Icon, I don't know which I'd choose.
posted by treepour at 1:50 PM on May 9, 2007

I'm sitting here at my desk. I'm eating Red Beans And Rice with Cornbread and wiping the tears from my eyes. I told my co-worker "it's because of the peppers." Fucking sad songs indeed!
posted by winks007 at 1:51 PM on May 9, 2007

X: "The whole world loves a sad song and they don't have to sing."

Sinatra's version of "One for My Baby (and One More for the Road)" [warning: cheesy video] is sadder than "In the Wee Small Hours of the Morning."

Floyd Cramer's "Last Date" is pretty sad (R.E.M.'s cover is sadder).

Billy Bragg, "Tank Park Salute"
"You were so tall/How could you fall?"
RIP: Dad, 1993
posted by kirkaracha at 1:51 PM on May 9, 2007 [2 favorites]

The entirety of Neil Young's On the Beach is an elegant bummer, particularly "Motion Pictures (For Carrie)," "Ambulance Blues" and the title track.

on preview: dittoing Lou's Berlin, especially "Sad Song" - the venom he delivers in the line "Somebody else would have broken both of her arms" has always floored me.
posted by porn in the woods at 1:52 PM on May 9, 2007

What? This is pop, right? They forgot The Cure's A Letter To Elise.

Every "top" list is subjective, I know, but considering its title, this list is quite underwhelming. Not sad enough!
posted by Lush at 1:52 PM on May 9, 2007

No (any other band but the 25 included)?! Shit and Goddamn!
posted by billypilgrim at 1:53 PM on May 9, 2007

Also, who the hell is Amy Winehouse and why exactly does every media outlet all of a sudden think I should care?
posted by billypilgrim at 1:54 PM on May 9, 2007

Every time I see one of these best of, worst of, saddest of lists, I get the feeling they were written by some goddamn iTunes marketing intern. And that the whole Internet is just one gigantic content-free advertising link. Plus porn.

Oh, and here's my obligatory "what, no Daniel Johnston? no Townes Van Zandt?"

grumps off to sulk
posted by M.C. Lo-Carb! at 1:55 PM on May 9, 2007

I just had a great idea for a website. It would be like karaoke, but it wouldn't be individual performances. It would be everyone who was visiting the site singing together. Anyone could request a song title, and the site would cycle through all of the requested songs, putting up the lyrics and playing the music in the background, and if you knew it and felt like singing, you would just sing into your computer microphone from home, and over your speakers you would hear the sound of thousands of people singing along with you. If you had a webcam then you could sing into it, and your computer screen would show like tiled pictures of everyone who was singing. It would be great! Imagine if everyone in this thread could sing all the songs that we were listing together. It would be like that old commercial where they wanted to teach the world to sing in perfect harmony. It could bring about world peace. Former enemies would be friends, because how can you hate someone that you just sang 'Band of Gold' with? I think that this is the idea that is really going to catapult me to the top. I will call it like www.singalong.com, but something not that lame. It will be the most popular website of all time. It will change the world. Nobody steal this idea.
posted by ND¢ at 1:56 PM on May 9, 2007 [30 favorites]

Agreed with many above. I can think of more sad songs in five minutes, and yes, it is heavy on the cohen, drake, and Elliott Smith -- well every song he ever wrote. Gary Jules' Mad World cover. And Cats in the Cradle, overplayed as it is, totally makes me tear up.

Lame list. But great link, as now we can point out what SHOULD have been there.
posted by John Kenneth Fisher at 1:56 PM on May 9, 2007

"Buy My Shirt Now Fanboy" by The Haugheys.
posted by Dizzy at 1:57 PM on May 9, 2007 [4 favorites]

I'd put Janis Ian's "At Seventeen" up there. Made me want to hide under a rock for weeks.
posted by fish tick at 1:58 PM on May 9, 2007 [2 favorites]

I wish someone out there knew what song is actually the saddest song... it would save up so much debate.
posted by ORthey at 1:58 PM on May 9, 2007

myself, i'm disappointed by the absence of "the song is you".
posted by pxe2000 at 1:59 PM on May 9, 2007

Jay Ungar's "Ashokan Farewell," which was used as the theme for Ken Burns' The Civil War, is the saddest song ever.

AskMetaFilter: What are the saddest songs?
posted by kirkaracha at 1:59 PM on May 9, 2007

What makes a sad song? A song that makes you sadder? A song that makes you smile through your tears? A song that makes you relate to the singer in its desperate blackness but is ultimately redemptive and cathartic?

I never thought Hallelujah was all that sad, really. And No Surprises is really just a wonderful murmuring prayer lamenting alienation and detachment from society. Space Oddity? Too much of a story - a wonderful song, but the suspension of disbelief only extends so far as the protagonist, not the singer, a world of difference to me on the sadness scale.

Now, Hurt and Here Comes a Regular, this is the stuff of legend: songs that hit you like a parched-mouthed, sleepless Sunday dawn that we - young men, the standard-bearers of sad songs, for better or for worse - can all relate to.

Still to me, those are nothing compared to Nothing Compares 2 U, a gut-wrenching masterpiece that for all its mawkish pop overtones - remember, this is not about genres - reminds us that in rock & roll, only one thing is sadder than all death and depression combined: the nameless ache of Big Love, and the desperate void of what comes after, for which the best, and possibly only, medicine is wallowing in that very same pain, aided by a brilliant song that affirms and reinforces your sadness and at the same time provides that sick, ironic catharsis that only a great song can offer.
posted by goodnewsfortheinsane at 2:01 PM on May 9, 2007 [1 favorite]

Not perhaps the most sad pieces, but

Adagio in sol minor - Albinoni
Kol Nidrei - Bruch
Solveig's song - Peer Gynt - Grieg
Concerto de Aranjuez - Rodrigo
Suite for violin & orchestra A minor - Sinding

Have been shown by SCIENCE! to consistently evoke sad affective states in listeners by way of brain scanning and self reportage.
posted by porpoise at 2:02 PM on May 9, 2007 [1 favorite]

Gilbert O Sullivan....Alone Again Naturally.
posted by doctorschlock at 2:03 PM on May 9, 2007

The song that gets me in the gut every time?
Sleater-Kinney's "The Size of our Love"
posted by SBMike at 2:05 PM on May 9, 2007

I'm So Lonesome I Could Cry = saddest song I've ever heard.

This list is just like all lists....subjective bullshittery
posted by GavinR at 2:06 PM on May 9, 2007

The Beatles.....Julia.
Joni Mitchell..A Case of You
Brian Eno...Put a Straw Under Baby
posted by doctorschlock at 2:06 PM on May 9, 2007

Tom Waits, "On The Nickel"
Johnny Cash, "Long Black Veil"
Sufjan Stevens, "Casimir Pulaski Day"
Simon & Garfunkel, "The Dangling Conversation"
Gretchen Wilson, "I Don't Feel Like Loving You Today"
Son House, "Death Letter Blues"
Neil Young, "Long May You Run"
Fred Eaglesmith, "Spookin' The Horses"
posted by arto at 2:09 PM on May 9, 2007 [1 favorite]

...and no songs from The The's Dusk either...
posted by NationalKato at 2:11 PM on May 9, 2007

Bobby "Blue" Bland's version of St. James Infirmary:
"She's gone....she's gone...she's...goooonnnnne."
posted by ColdChef at 2:12 PM on May 9, 2007

The Band...The Weight
Brian Eno...Spider and I
Joni Mitchell...Hejira...Amelia
James Taylor.....Don't Let Me be Lonely Tonight
Innocence Mission...Every Hour Here
Harold Melvin and the Blue Notes....If You Don't Know me by Now
Don McLean...Vincent

Lordy...they got me started....
posted by doctorschlock at 2:12 PM on May 9, 2007

more sad hits:

Palace Brothers - "Come In" b/w "Trudy Dies" 7" single

American Music Club - "Western Sky," "Cape Canaveral"

Mark Eitzel - "Everything is Beautiful," "Live or Die," "Some Bartenders Have the Gift of Pardon"
posted by porn in the woods at 2:14 PM on May 9, 2007 [1 favorite]

I totally forgot about Joni Mitchell. I can't listen to that song "River" but once a year for exactly this reason.
posted by kid ichorous at 2:14 PM on May 9, 2007

Amy Winehouse on the same list as Billie Holiday for any reason whatsoever (even "list of people who are female") makes me want to vomit.
posted by zarah at 2:14 PM on May 9, 2007

Moxy Fruvous, "The Drinking Song." Especially from a band that could produce "King of Spain" or "Green Eggs and Ham."
posted by darksasami at 2:15 PM on May 9, 2007

Aretha Franklin..You Make Me Feel Like A Natural Women
posted by doctorschlock at 2:15 PM on May 9, 2007

When I was a lad
And old Shep was a pup
Over hills and meadows we'd stray
Just a boy and his dog
We were both full of fun
We grew up together that way

I remember the time at the old swimmin' hole
When I would have drowned beyond doubt
But old Shep was right there
To the rescue he came
He jumped in and then pulled me out

As the years fast did roll
Old Shep he grew old
His eyes were fast growing dim
And one day the doctor looked at me and said
I can do no more for him, Jim

With hands that were trembling
I picked up my gun
And aimed it at Shep's faithful head
I just couldn't do it
I wanted to run
I wish they would shoot me instead

He came to my side
And looked up at me
And laid his old head on my knee
I had struck the best friend that a man ever had
I cried so I scarcely could see

Old Shep he has gone
Where the good doggies go
And no more with old Shep will I roam
But if dogs have a heaven
There's one thing I know
Old Shep has a wonderful home

...*BAWWWWWWWWWWW!!!*

(PS: This list sucks. "The River" really is pure cyanide in music form, though.)
posted by kittens for breakfast at 2:16 PM on May 9, 2007 [1 favorite]

The River is so far from Bruce's saddest song it should instead be at the top of a list entitled "Songs Which Are Not Bruce Springsteen's Saddest, You Nitwit."

Also:
We're listing what's left:
A signed Slayer t-shirt,
A car up on blocks in his mother's back yard.
posted by wemayfreeze at 2:17 PM on May 9, 2007

(That was not intended to be aimed at you, kittens for b., you just got in the way of the blast!)
posted by wemayfreeze at 2:18 PM on May 9, 2007

No Oomingmak? No Pink Orange Red? No This Mortal Coil? Pfff. This is a nice list. for me to poop on
posted by everichon at 2:18 PM on May 9, 2007

There was a time when This Woman's Work would drive me to tears, but I think watching the incredibly cloying video just now has cured me of that reaction.
posted by lalex at 2:19 PM on May 9, 2007

Terry Jacks...Seasons in the Sun
?......Ode to Billy Joe
posted by doctorschlock at 2:20 PM on May 9, 2007

Johnny Darrell's "Ruby, Don't Take Your Love To Town"
posted by Floydd at 2:20 PM on May 9, 2007

I'm still mourning over Shep, wemayfreeze. But go on -- kick a man while he's down!
posted by kittens for breakfast at 2:20 PM on May 9, 2007

Terry Jacks...Seasons in the Sun
posted by doctorschlock

Eponysterical!
"We had joy we had fun
we had seasons in the sun."
posted by Floydd at 2:22 PM on May 9, 2007

W.O.L.D.
Taxi......Harry Chapin
posted by doctorschlock at 2:22 PM on May 9, 2007

Oh, and some totally subjective and personal nominations:

-Sad because longing and plaintive: Whiskeytown - Avenues (really just Ryan Adams)^*
-Sad because frustrated and disappointed, with an oddly cathartic tinge: The Smiths - There Is a Light That Never Goes Out
-Sad because hey, youth is wasted on the young: Elbow - Scattered Black & Whites (thank you, stopgap!)
-Sad because hey, life is wasted on the living: Flaming Lips - Do You Realize?

-And, because as I tried to illustrate above, the saddest form of sadness in music is the angry desperation of heartbreak: Robyn - Be Mine

^*: Thanks to O. (who will eventually read this) for turning me onto this, and for ruining my taste in music altogether. I love you, you wonderful snob.
posted by goodnewsfortheinsane at 2:25 PM on May 9, 2007

Promises...Eric Clapton
The Flying Lizards...The Window
posted by doctorschlock at 2:26 PM on May 9, 2007

Snow Patrol, "Run"
posted by po at 2:26 PM on May 9, 2007

wemayfreeze, I never actually paid attention to what that song was about before (I'd always figured it was something to do with a garage sale).
And hey, on that website you can get it as a ringtone
posted by Flashman at 2:27 PM on May 9, 2007

"Golden Age" by Beck.

And seconding "Tank Park Salute" by Billy Bragg. Jesus, that's a weeper just remembering the lyrics, aside from being brilliant songwriting.
posted by docpops at 2:27 PM on May 9, 2007

hi,

sure the question is "why does it state "the whole world" ?".

what about Jacques ?

and if you really want to be sad, try anything by leo : like this.

So sad it just makes me feel like laughing.

And what about the other countries ?
posted by nicolin at 2:28 PM on May 9, 2007

I'm not really one to get terribly emotional about songs, but The Grave by Don MacLean is particularly sad. I also find the first movement of Beethoven's Moonlight Sonata pretty miserable, especially when played by a proper pianist.
posted by Aloysius Bear at 2:29 PM on May 9, 2007

"Gulf Shores" by Will Oldham. (lyrics)
posted by Atom Eyes at 2:29 PM on May 9, 2007

Vince Guaraldi....Cast Your Fate to the Wind
posted by doctorschlock at 2:31 PM on May 9, 2007

Todd Rundgren...Hello It's Me (My Personal tearjerk song)
posted by doctorschlock at 2:33 PM on May 9, 2007

I wasn't expecting to see Khanate's No Joy but nothing from Low?

False.
posted by The Straightener at 2:33 PM on May 9, 2007

Mrs. Winks007, said the song "Don't take the Girl - Tim McGraw will have you sawing on your wrists with the sharp edge of a ruler in no time at all.

Johnny's daddy was taking him fishing
when he was eight years old.
a little girl came through the front gate
holding a fishing pole
his dad looked down and smiled
said we can't leave her behind
son I know you don't want her to go
but someday you'll change your mind
and Johnny said
take Jimmy Johnson
take Tommy Thompson
take my best friend Bo-
take anybody that you want as
long as she don't go
take any boy in the world

daddy please- don't take the girl

Same old boy
same sweet girl
ten years down the road
he held her tight and kissed her lips
in front of the picture show
Stranger came and pulled a gun
grabbed her by the arm
said if you do what I tell you to do
there won't be any harm
and Johnny said
take my money
take my wallet
take my credit cards
here's the watch that my grandpa gave me
here's the keys to my car
mister give it a whirl
but please-don't take the girl

Same old boy
same sweet girl
five years down the road
there's gonna be a little one
and she says it's time to go
docter says the baby's fine
but you'll have to leave
cause his momma's fading fast
and Johnny hit his knees
and there he prayed
take the very breath you gave me
take the heart from my chest
I'll gladly take her place
if you'll let me
make this my last request
take me out of this world
God please-don't take the girl

Johnny's daddy was taking him fishing
when he was eight years old.

I'm not even gonna finish reading those lyrics!
posted by winks007 at 2:33 PM on May 9, 2007

Some songs are musically sad, independent of the lyrics. O Mio Babbino Caro chokes me up every time--and I don't, in general, like opera, get emotional about songs, or even understand the words. Go figure.
posted by weapons-grade pandemonium at 2:34 PM on May 9, 2007

That W.O.L.D. is a great song. I cant think of the same or the artist, but there was a song about a guy who comes home and see's a brand of cigs (not his) on the table and says " I know who left those smokes behind, something about him, him, him?

I guess Harry Chapman would prolly take 5 of the top 25 songs. Also...Jimmy Buffet can break your heart with such classics as: Son of a Son of a Sailor.
posted by winks007 at 2:38 PM on May 9, 2007

not a horrible list, but they left out so many...

To Wish Impossible Things/Cure (and maybe Pictures of You too) needs to be there.
posted by amberglow at 2:41 PM on May 9, 2007

Rupert Holmes....Him
posted by doctorschlock at 2:42 PM on May 9, 2007

what about metallca's fade to black? its about wanting to commit suicide because of lifes changes.thats sader than the beegees
posted by fire&wings at 2:42 PM on May 9, 2007

DoctorSchlock you wouldn't by any chance be 40.5 years old, huh?
posted by winks007 at 2:44 PM on May 9, 2007

Kansas - Carry on my Wayward Son.
posted by winks007 at 2:44 PM on May 9, 2007

Delta Dawn...Helen Reddy
posted by doctorschlock at 2:44 PM on May 9, 2007

Dust in the Wind
posted by doctorschlock at 2:45 PM on May 9, 2007

Is it just me, or was it quite annoying that this website didn't bother to list the albums on which these track appeared (and why is "Gloomy Sunday," with its happy ending on there?).

Further, I must mention that for some reason the song that first came to mind when I heard this list was Tom Waits's "A Little Rain." Which I'm not even so sure is really a good song. I mean, it's a waltz that begins with a German dwarf dancing with a butcher's son, which sure seems like a facile obscurity included as a weak gesture to hide the song's obvious waltzy/schmaltzy sentimentality.

But yet there the song is in my mind, pressing its claim. I guess it just sticks with me. There are also good sad songs by trendy popular bands like Bright Eyes, and Death Cab for Cutie. A deep and rich vein of sadness can be found (surprisingly?) in They Might be Giants tunes, too.
posted by washburn at 2:45 PM on May 9, 2007

You got me, Winks.
posted by doctorschlock at 2:45 PM on May 9, 2007

Arg, no PIAF!

It is a horrible list.
posted by lupus_yonderboy at 2:45 PM on May 9, 2007

Not that anyone would know it, but "Le Monster," by My Favorite. When I first heard this song on the road, it was a complete "I wanna jerk the wheel INTO A GODDAMNED BRIDGE ABUTMENT" moment.
posted by adipocere at 2:46 PM on May 9, 2007

W.O.L.D.
Taxi......Harry Chapin

And the aforementioned "Cat's in the Cradle," and "Mr. Tanner" - heck, you could put half of Harry Chapin's entire corpus on this list.

Also, Pink Floyd, "Wish You Were Here"

However, from Miko way up above: I'd have put Paul Simon's American Tune on the list.

Really? One of my favorite songs, but I've never thought of it as all that sad. It's ultimately hopeful, IMO.
posted by DevilsAdvocate at 2:49 PM on May 9, 2007

washburn, if it's any consolation I find it touch-and-go whether not I can listen to "A Little Rain" at all. Too painful a song sometimes (and there's no personal history getting kicked with it, either, it just ow ow ow). Makes Warren Zevon's version of "Back in the High Life Again" downright cheery, it does.
posted by dilettante at 2:49 PM on May 9, 2007

"Heartbreak Hotel," people.
posted by escabeche at 2:50 PM on May 9, 2007

Parsley, Sage Rosemary, and Thyme...Simon and Garfunkel
(The whole album while you're at it.)
posted by doctorschlock at 2:51 PM on May 9, 2007

"Honey" - Bobby Goldsboro
"Bobby MgGee" - Kris Kristoferson
"Sunday Morning Coming Down" - Kris Kirstoferson
"Blue Eyes Crying in the Rain" or "Angels flying too close to the Ground" - Willy Nelson
"Green Green Grass of Home" (Tom Jones?)
"The Grave" - Don McClean
posted by The Light Fantastic at 2:52 PM on May 9, 2007

Maureen McGovern...The Morning After
posted by doctorschlock at 2:52 PM on May 9, 2007

Needs more Wrens.
posted by MarshallPoe at 2:53 PM on May 9, 2007

The Wreck of the Edmond Fitchgerald..Gordon Lightfoot
posted by doctorschlock at 2:53 PM on May 9, 2007 [2 favorites]

Led Zepplin....Going to California
posted by doctorschlock at 2:55 PM on May 9, 2007

Weak, weak, weak. And this top-X-list-click-per-each-blogger-SEO crap needs a glassen.

In addition to the aforementioned missing artists, I offer this Gilbert O'Sullivan classic.
posted by flotson at 2:56 PM on May 9, 2007

The Orbison choice proves they're just being willfully contrarian. While it's a fine song, it's not in the same league as "Crying" or "In Dreams" or even "Only the Lonely."

Also: where's Hank Sr.?
posted by Rangeboy at 2:56 PM on May 9, 2007

Without Cohen's Famous Blue Raincoat, this post is all wet.
posted by 2sheets at 2:59 PM on May 9, 2007 [1 favorite]

I second that Gary Jules' Mad World cover should be on this list.

And Radiohead's No Surprises? While I doubt anyone is surprised they're on the list (it's kinda expected) I woulda thought we'd see "Street Spirit" or "How to Disappear Completely".
posted by Windigo at 3:01 PM on May 9, 2007

I'd definitely put "Anna Begins" by the Counting Crows on that list... ever since I read about the history of that song, I can't help but start crying every time I hear it. Heck, my eyes water up just thinking about it now.
posted by evilangela at 3:03 PM on May 9, 2007

The list never had a chance. 25 songs? It would have been better to divide it up into 25 country, 25 blues, etc.

And for the record, the saddest song I've heard lately is "Kilkelly Ireland". The lyrics were based on a stash of letters the writer found, written to his great-grandfather by his great-great-grandfather across a span of over thirty years.
posted by Faint of Butt

Agreed. I actually first heard that song in Ireland. I've seen singers in the U.S. refuse to do that song because it's too much of a downer.

Sinatra's version of "One for My Baby (and One More for the Road)" [warning: cheesy video] is sadder than "In the Wee Small Hours of the Morning."
posted by kirkaracha

It's really criminal to break up either of those albums as the total effect is much more depressing than any one song. Strangely, I always thought "one for my baby" to be more of an uplifting song compared to the rest. It has more of an 'I'm accepting my fate but here's to her before moving on' vibe going on.

I guess for a Sinatra song I'd go with "It Never Entered My Mind", though I think it's actually a Miles Davis song.

If I had to pick a song not mentioned I guess I'd go with Skip James Washington D.C. Hospital Center Blues.
posted by justgary at 3:03 PM on May 9, 2007

May this list never die!
posted by doctorschlock at 3:05 PM on May 9, 2007

The Saddest Music in the World
posted by DevilsAdvocate at 3:08 PM on May 9, 2007

Elvis Costello's - "I Want You" is the saddest song I have ever known. And I have everything Elliott Smith ever did. I think of Elliott as a sad person, but his songs don't make me sad. Except "Bye" - but that only makes me cry because he's dead.
posted by pinky at 3:12 PM on May 9, 2007

In the corner see his face
The man just sips his drink
Not one feeling does he show
Far too numb to think
He does not say a single word
No word of love to say
Maybe he will soon believe he's better off this way...

"Brief Candles" - The Zombies
posted by mauglir at 3:13 PM on May 9, 2007

Come on, no Queen? None at all? What about Who Wants to Live Forever? Too melo? Okay, fine. The Show Must Go On, that's so bloody sad for inter and metareasons that it makes me sad just thinking about the reasons!
posted by headspace at 3:14 PM on May 9, 2007

Second on Strange Fruit, and I probably would've called for "Fairytale of New York, because that one makes me cry like a baby every time, though I guess it's happy at the end.

Also, I guess I'm five years too late and ten years too old to be pushing for Death Cab, but "What Sarah Said is still a gorgeous, devastating song about being helpless as a loved one dies, and hoping that just being ther is enough.
posted by Navelgazer at 3:15 PM on May 9, 2007

The last verse of "Puff the Magic Dragon" always brings a tear to my eye....when Jackie Paper grows up and no longer comes to play.

And I agree, "Cat's in the Cradle" should be on that list. And "Alone Again, Naturally."
posted by Oriole Adams at 3:19 PM on May 9, 2007 [1 favorite]

SEASONS IN THE SUN ?
posted by Flood at 3:19 PM on May 9, 2007

Piff! No This is the Saddest Song that Ever Was and Ever Will Be by "The Singers of the Saddest Songs in the History of Forever"???

Wha??????????????
posted by The Deej at 3:20 PM on May 9, 2007

And where are the Cowboy Junkies in that list?

Seriously.

I agree also with Seasons in the Sun, which first popped into my mind when I read the FPP. And the next, off the top of my head, would be Condition of the Heart by Prince. And maybe The Lost Soul by the Watson Family.

I'm sure I could come up with more since I have a bunch of utterly depressing songs in my library (at home), though certainly not as eclectic as this thread in sum.
posted by effwerd at 3:21 PM on May 9, 2007

Yeah, that was the worst list ever.

More missing songs:

Superman's Song - The Crash Test Dummies
Trust - The Cure
posted by jeffamaphone at 3:22 PM on May 9, 2007

"Candle Chant", DJ Krush
"Happy Happy Joy Joy", Stinky Wizzleteats
posted by erniepan at 3:29 PM on May 9, 2007

I'd like to add Pearl Jam's Black, Evanesence's (piano-only) version of My Immortal and A Perfect Circle's 3 Libras as 3 really sad songs that made me blub like a little girl following a breakup with an ex-girlfriend.
posted by Effigy2000 at 3:32 PM on May 9, 2007

Sweet Dreams - Patsy Cline
posted by hojoki at 3:35 PM on May 9, 2007 [1 favorite]

"I Can't Make Your Love Me" by Bonnie Raitt
posted by tristeza at 3:35 PM on May 9, 2007

Cloud Cult has a song about his lost infant that drove me to tears last time I saw them play.
posted by yeti at 3:40 PM on May 9, 2007

Needs more murder ballads.
posted by basicchannel at 3:44 PM on May 9, 2007

No Townes Van Zandt?!?!? WTF?

Random Lyric:
Friends, when my time comes,
As surely it will,
Carry my body up to some lonesome hill.
Lay me down easy, where the cool rivers run,
Nothin' behind me, but the shadow of the sun.
posted by notsnot at 3:44 PM on May 9, 2007

I'm glad someone seconds "A little rain," dilettante. An interesting thread. If this were a bar instead of web forum, it'd be fun to raise the question of what counts as a "sad" song or saddness, anyhow. But it's a web forum, after-all, so it's back to work for me!
posted by washburn at 3:47 PM on May 9, 2007

-Sad because hey, youth is wasted on the young: Elbow - Scattered Black & Whites

Ah, no, that song isn't sad, it's... something else. It's about sheltering in the memories of childhood. It's elegiac, that's what it is.

And: Cowboy Junkies, To Love is to Bury. Oh god.

Also another vote for How To Disappear Completely instead of No Surprises. That song tears me into pieces, in the best possible way.

That horrific chord which signifies Mimi's death in La Boheme... just after that "Corragio!" which breaks my heart every time.

And the ultimate: Vissi d'arte, from Tosca:

I lived for my art, I lived for love,
I never did harm to a living soul!
With a secret hand
I relieved as many misfortunes as I knew of.
Always with true faith
my prayer
rose to the holy shrines.
Always with true faith
I gave flowers to the altar.
In the hour of grief
why, why, o Lord,
why do you reward me thus?
I gave jewels for the Madonna's mantle,
and I gave my song to the stars, to heaven,
which smiled with more beauty.
In the hour of grief
why, why, o Lord,
ah, why do you reward me thus?
posted by jokeefe at 3:47 PM on May 9, 2007

No love for Dylan? A lot of the recent stuff is drenched in sorrow, like "Not Dark Yet" off Time Out of Mind or "When the Deal Goes Down" from Modern Times.
posted by muckster at 4:01 PM on May 9, 2007

Oh, and I'd like to second "Sometimes It Snows In April" by Prince (who also wrote "Nothing Compares 2U", of course.)
posted by muckster at 4:03 PM on May 9, 2007

Wot? No sad, sad love for:

Heart as pure as rust - The Anaemics
Ever so much less - James Caliban
Torching - New Musical Suprise
Shining silver needle - Art Matthews
or (my personal all-time tear-jerkin' fave)
You are a huge bunch of sooks - by "yes, I did just make up all these songs""
posted by Sparx at 4:05 PM on May 9, 2007 [2 favorites]

"Gloomy Sunday" is so sad that it's said to have inspired a wave of suicides. There's a movie about it.
posted by muckster at 4:06 PM on May 9, 2007

You're all wrong. Because it's simply impossible to make a list of the "Top 25 sad songs". There's no such list, it's too subjective.

That is all.
posted by Justinian at 4:06 PM on May 9, 2007

Agree with "Naked as We Came", "Brick" and "Eleanor Rigby." Second Gilbert O'Sullivan's "Alone Again, Naturally." Add "Walk Away Rene" by Left Banke.
posted by Turtles all the way down at 4:06 PM on May 9, 2007

Oh, but "And the Band Played Waltzing Matilda" is pretty fucking sad.
posted by Justinian at 4:07 PM on May 9, 2007

It's a rare post that can inspire this level of sturm und drang.


Here's my vote: Time (The Revelator)
posted by chuckdarwin at 4:11 PM on May 9, 2007

Morphine's "Gone for Good" is conspicuously absent.
posted by mullingitover at 4:12 PM on May 9, 2007

"I Can't Make Your Love Me" by Bonnie Raitt

Enthusiastic second, tristeza.
posted by Turtles all the way down at 4:13 PM on May 9, 2007

There is no Elliot Smith because he is Emo, not Sad. There is a difference. One is whiny the other is melancholy.

Also, I cant believe there wasnt
"Sad Songs" by Elton John
or
"There'll be sad songs" by Billy Ocean. What gives?


Also, I might have to vote for "Mercy Seat" covered brilliantly by Johnny Cash.

And its a good thing they are not including songs from Musicals, because I can think of 25 just from a handful of musicals...
posted by subaruwrx at 4:16 PM on May 9, 2007

"Without You" by Harry Nilsson is a monstrously sad song made all the more heartbreaking by the stark relief of "Coconut".

I think "Fox in the Snow" by Belle and Sebastian is really sad too.

You know what else is sad? This fucking list.
posted by I Foody at 4:17 PM on May 9, 2007 [1 favorite]

Marie -- Townes Van Zandt

A clear victor in the race to the salt sea. So sad it makes me vaguely ill to think about.
posted by LucretiusJones at 4:18 PM on May 9, 2007

Oh and "Miss Being Mrs." by Loretta Lynn actually had me weeping but I was on mushrooms so I'm not sure if it counts.
posted by I Foody at 4:20 PM on May 9, 2007

Fredo Viola - The Sad Song (awesome video)
posted by Espoo2 at 4:21 PM on May 9, 2007

Big Mamma Thornton - Ball & Chain
Etta James - I'd Rather Go Blind
T-Bone Walker - Stormy Monday
Lightnin Hopkins - Going Down Slow
Stevie Ray Vaughn - Texas Flood
Otis Redding - I've Been Loving You Too Long
Randy Newman's - Louisiana 1927 -also, Aaron Neville
various - Cry Me a River
Elvis Costello - Almost Blue
Ry Cooder - He'll Have To Go
Ian & Sylvia - Rio Grande

seconding: Strage Fruit, I'm So Lonesome I Could Cry, At Seventeen, I Can't Make You Love Me
posted by madamjujujive at 4:30 PM on May 9, 2007

What an incredibly weak list of sad songs.

Staying within the category of popular music, I'm SHOCKED that Tim Buckley's "Song To The Siren" hasn't been mentioned yet.

Admittedly, a "saddest songs in the world" list is relative only to the audience it is written for, but come on, Amy Winehouse, Iron & Wine?
posted by nataaniinez at 4:33 PM on May 9, 2007 [2 favorites]

This list is missing both "The Dock of the Bay" and "Beyond the Sea".

And they picked the wrong Ben Folds Five song. They should've gone with "Evaporated".
posted by The Great Big Mulp at 4:35 PM on May 9, 2007

Richard Thompson's Taking My Business Elsewhere
posted by flapjax at midnite at 4:36 PM on May 9, 2007

Your favourite song is downright chipper.
posted by Schlimmbesserung at 4:50 PM on May 9, 2007 [5 favorites]

Dude. The saddest Tom Waits song is so totally A Christmas Card From A Hooker In Minneapolis, I can't even take it. So sad. And so, so, the greatest song ever written of all time ever.
posted by mckenney at 4:50 PM on May 9, 2007

Ian & Sylvia - Rio Grande

Oooh, Four Strongs Winds.

And where's the Neil Young? Where's Helpless, which should be on any list of sad songs? Just thinking of the first line makes me shiver... There is a town in North Ontario....
posted by jokeefe at 4:52 PM on May 9, 2007

^^^

Strong. Whoops.
posted by jokeefe at 4:52 PM on May 9, 2007

Pretend I never happened
And erase me from your mind
You will not want to remember
Any love as cold as mine
I'll be leaving in the morning
For a place I hope I find
All the places must be better
Than the ones I leave behind
-Willie Nelson
posted by landis at 4:55 PM on May 9, 2007

inconsequentialist writes "I vote for Willie Nelson's 'Always on My Mind.'"

Or "Angel Flying Too Close to the Ground." Or "Blue Eyes Crying in the Rain." (mentioned previously in the thread, I see ...)

Or Derek and the Dominoes, "Why Does Love Got to Be So Sad?" Or, really, almost anything on "Layla and Other Assorted Love Songs". Probably the saddest album, best to get you through a breakup, but hard to make it through the whole thing because it's so painful.

Or John Lee Hooker's "My Dream."
posted by krinklyfig at 4:56 PM on May 9, 2007

I vote for Meatloaf's "Objects in the Rear View Mirror (May Appear Closer Than They Are)"
posted by jmd82 at 5:00 PM on May 9, 2007

John Prine's Angel From Montgomery
posted by flapjax at midnite at 5:02 PM on May 9, 2007 [1 favorite]

That Chocolate Genius song is sadder than the entire list. Seriously, check it out.
posted by KevinSkomsvold at 5:03 PM on May 9, 2007

Hey! Lets all post our favorite sad song, and make this a monstrously long thread that there's no way we can read through in one sitting!

Mine's "No Regrets" by Ultravox. Yeah, Ultravox. Deal with it.

There's no regrets - no tears goodbye - I don't wan't you back - we'd only cry again Say goodbye again!
posted by yhbc at 5:09 PM on May 9, 2007

"Let The Happiness In" by David Sylvian - the soundtrack to my three o'clock in the mornings when everything terrible is even worse:
I'm waiting on the empty docks
Watching the ships come in
I'm waiting for the agony to stop
Oh, let the happiness in
I'm watching as the gulls all settle down
Upon the empty vessels
The faded whites of their wedding gowns
The songs of hopeless selflessness
The cold December Sun
A cold that blisters
The hands of a working man
Wasted
I'm waiting on the empty docks
Watching the ships roll in
I'm longing for the agony to stop
Oh, let the happiness in
Oh, let the happiness in
Listen to the waves against the rocks
I don't know where they've been
I'm waiting for the skies to open up
And let the happiness in

Also, for Radiohead, there is nothing sadder than "Fake Plastic Trees". And I am unanimous in this.
posted by biscotti at 5:10 PM on May 9, 2007

It's a good list of sad songs, but there is absolutely no way it is THE list of sad songs. The future compiler of THE list should, however, take a glance at the attempt linked in the FPP just to make sure they aren't missing anything.

Unfortunately for this good list of sad songs, it's done in an unimaginably poor layout seemingly designed solely to increase overall pageviews. Not yay.

Just reading the description of the Chocolate Genius song made me cry, so anyone compiling a new list should keep that one in mind, for certain.

All of that said, it's a good link and a good post - the conversation that has resulted will keep me busy on the sad song front for YEARS.
posted by batmonkey at 5:12 PM on May 9, 2007

Clearly Casimir Pulaski Day by Sufjan Stevens is the saddest song in the world. I listened to it over and over and over again when a friend was dying of cancer last Spring and I cried every single time. See also: Funeral by Band of Horses
posted by fancypants at 5:13 PM on May 9, 2007

Peggy Lee's "Is that all there is?"
posted by razzuli at 5:14 PM on May 9, 2007 [1 favorite]

South Tacoma Way - Neko Case and Her Boyfriends (most of that album really)
Special - Justin Rutledge and the Junction Forty
Hearing Aid - They Might Be Giants (unlikely but this song always strikes me as sad, especially that last "because")
Already Dead - Beck
Dirt Floor - Chris Whitley
Am I a Good Man? - Them Two
Country Feedback - REM
House of the Risin' Sun - Bob Dylan (or Boots of Spanish Leather)
Cemetary Gates - Pantera (I don't like anything else by this band, but that guitar riff just gets me)
Don't Give Up - Peter Gabriel
posted by effwerd at 5:15 PM on May 9, 2007

Elliott Smith is not whiny, sheesh. He is however often sad in that way that junkies often are. I met him a few times in real life, he was always happy albeit drunk but never whiny and never anything akin to emo.
posted by yodelingisfun at 5:17 PM on May 9, 2007

Notable missings:

The entire album In the Aeroplane Over the Sea by Neutral Milk Hotel. I, to this day, don't listen to this on the bus or train so as to not start crying in public.

The entire album Tallahassee by Mountain Goats. Also can't listen to this one on public transit.

Divorce Song by Liz Phair.
posted by misskaz at 5:18 PM on May 9, 2007

It will never show up on anyone's list, but I challenge anyone to play Aeris' theme from FF7 around someone who's played the game without getting at least some effect.

Aside from that, I think 'Blasphemous Rumours' from Depeche Mode is my suggestion least likely to encourage mockery of my unspeakably bad taste in music.
posted by Mitrovarr at 5:20 PM on May 9, 2007

There are a lot of clunkers in that list, and they missed three classics not mentioned so far:

"Don't Let the Sun Catch You Crying," Gerry & the Pacemakers

"Fire & Rain," James Taylor

"Rusty Water," Jason Eklund

But they did get "Hallelujah," by Jeff Buckley. All I can say is keep the vodka and the knives under lock and key when you listen to that one. It's #16 on their list and it ought to be #1. Excuse, I have to go cry now. (sniff)(sniff)
posted by Charles Wilson at 5:31 PM on May 9, 2007

As fancypants says, Sufjan Stevens: Casimir Pulaski Day is terribly sad (and great), as is Will Oldham: Break of Day. But to me they are sad in a "oh-that's-sad-but-they-lived-a-full-life" kind of way. Certainly another level of sadness has been attained in Cat Power: Names. Jesus that song is Sad.
posted by hgbrian at 5:36 PM on May 9, 2007

fancypants, you're right on the Sufjan, though for me, also, it is only reaches the depths it does because of personal experience.
posted by wemayfreeze at 5:38 PM on May 9, 2007

Seconding all of madamjujujive's songs (have you been hacking into my iTunes, mjjj?) and, like others, wondering about the dearth of Tom Waits, Joni Mitchell and Richard Thompson.

Also wanted to toss in the kitschy-sad "Emma" by Hot Chocolate ("awwwww EMMAline!").
posted by GrammarMoses at 5:39 PM on May 9, 2007

Hey, mckenney, no way: She'll be eligible for parole come Valentine's Day!

If that ain't hopeful I don't know what is.
posted by GrammarMoses at 5:44 PM on May 9, 2007

"strange fruit"as sung by nina simone?
"something in the way" by nirvana?
the utterly devastating "amy with a white coat on" by bright eyes?
"angels" by elliot smith?
"mr. bojengles" by david bromberg?
posted by es_de_bah at 5:47 PM on May 9, 2007

I forgot to add Jed's Other Poem by grandaddy. It's a song about a sad robot and it makes me cry.
posted by misskaz at 5:50 PM on May 9, 2007 [1 favorite]

Make that Jed the Humanoid, wrong robot song.
posted by misskaz at 5:56 PM on May 9, 2007

es_de_bah: Mr. Bojangles is by Jerry Jeff Walker.
posted by flapjax at midnite at 5:57 PM on May 9, 2007

Smog, "Rock Bottom Riser."
posted by Iridic at 5:58 PM on May 9, 2007

Artists I might have liked to have seen in the list: Cowboy Junkies, Swans, Patti Smith (c'mon...Birdland, for fuck's sake!), Portishead, hm, seconding And the Band Played Waltzing Matilda, Leonard Cohen, all kinds of ghazals, anything by Djivan Gasparayan, Cat Power, John Cale's Hallelujah, Dirty Three, Heaven up Here era Echo & the Bunnymen, Disintegration era Cure (eg The Same Deep Water as You), This Mortal Coil, Jacques Brel (!!!), Arvo Part & Henryk Gorecki (if modern classical counts), maybe something by The Cranes, and to finish I might suggest Godspeed! You Black Emperor! for the totally soulcrushing, despairing flavour of sadness.
posted by UbuRoivas at 6:00 PM on May 9, 2007

Lewis Allen's Strange Fruit, made famous by Billie Holiday, is certainly one of the tops in the 'really dark sadness' category.
posted by flapjax at midnite at 6:00 PM on May 9, 2007

Sia - Breath
Dar Williams - It Happens Every Day
Wheat - Don't I Hold you Like you Want
Sufjan Stevens - Widows of Paradise
Ani Difranco - Both Hands or Done Wrong
Amberlin - Amsterdam
BNL - What a Good Boy
Beatles - Yesterday
Microphones - The Moon
Ryan Adam's cover of Wonderwall or Hello Mrs. Lovely
Damien Rice - 9 crimes
Death Cab - Title and Registration
Del Amitri - Driving with the Brakes on
Deftones - Be Quiet and Drive
Elliott Smith - Everything Reminds Me of Her
Firescape - Wasted
Chris Crofton - Drown
Fiona Apple - Never is a Promise

I love sad songs.
posted by Bageena at 6:06 PM on May 9, 2007 [1 favorite]

"Down From Dover," by Dolly Parton, is pretty good.

A strange, one-off project called Spell, composed of goths from different bands, covered some of the most depressing music of the fifties, sixties, and seventies. They did "Seasons in the Sun." They did "Down from Denver." They even did "Johnny, Remember Me."

I still think Buckley's "The Last Goodbye" is pretty sobworthy. And, you know, most of The Smiths catalog.
posted by adipocere at 6:14 PM on May 9, 2007 [1 favorite]

Also, for Radiohead, there is nothing sadder than "Fake Plastic Trees". And I am unanimous in this.

How many of you are there?

(I'd also put Black Star or Bulletproof in there too, not to mention Motion Picture Soundtrack and Cymbal Rush, but I have to admit that the line "gravity always wins" is ten kinds of awesome).

And Casimir Pulaski day. Yeah. My father actually died, of cancer, on Casimar Pulaski Day. So you could say I have a personal connection to that song. And he takes, and he takes, and he takes...

Oh, and Silver Rider, by Low. Absolute yearning and crisis of faith, so beautifully expressed.
posted by jokeefe at 6:14 PM on May 9, 2007

saddest Beatles song: "In My Life"

saddest english language song ever? "Will the Circle Be Unbroken"

song that makes me cry, even though I shouldn't? "Love and Mercy" Brian Wilson

song that makes my wife cry? "All the Time In the World" by Lowen and Navarro (covering a Dave Moore song)

and I think we can all gives a "HELL YEAH" to the closing credits music on the final episode of Firefly. whatever it was...

I cry at dog food commercials though, so a macho man I aint...
posted by annasbrew at 6:37 PM on May 9, 2007

You know what's sad? That list. Space Oddity? What about Aladdin Sane? That's a sad song.

Saddest song of al time? Dusty Springfield's version of The Windmills Of Your Mind.

And who's this Amy Winehouse person? Is she the one who doesn't want to go to rehab? Well, let me just say that she was so wasted when she recorded that pice of dreck that she didn't notice that she accidentally used the drums from another song. Gah.
posted by Devils Rancher at 6:41 PM on May 9, 2007

You could always hold a contest to find The Saddest Music In the World.

"If you're sad, and like beer, I'm your lady."
posted by hurdy gurdy girl at 6:43 PM on May 9, 2007

modest mouse - life like weeds
tom waits - fish and bird
the cure - the same deep water as you
posted by brevator at 6:54 PM on May 9, 2007

"As Tears Go By"- I prefer the Stones to Marianne Faithful.
"Long Black Veil"- Bill Monroe's cover.
"I am a Rock"- Simon and Garfunkel.
"Cathy's Clown" by the Everly Brothers always gets me.
"I'm So Lonesome I Could Cry" -nth'd.
posted by oneirodynia at 6:54 PM on May 9, 2007

Also: "Fire Of The Mind" by Coil gets me every time. Dunno who Amy Winehouse is.
posted by everichon at 7:07 PM on May 9, 2007

nick cave and the bad seeds - where do we go now but nowhere?
posted by brevator at 7:17 PM on May 9, 2007

Am I the only one that thinks that number one on this list should be "The living years" - Mike and the Mechanics; followed closely by "Sandy and Little Andy" - Dolly Parton?
posted by ramix at 7:24 PM on May 9, 2007

I read somewhere that Dylan considered the saddest song he had ever written was 'I threw it all away'. That prompted me to search it out and yes, it is pretty damn sad.
And what about Sinatra with 'Summer Wind' or 'It was a very good year' Oh! the loss.
posted by tellurian at 7:28 PM on May 9, 2007

you mean to tell me there are more than 25 sad songs? shocking!
posted by quarter waters and a bag of chips at 7:30 PM on May 9, 2007

I can't even listen to Fairytale of New York without bawling. The fact that this list includes no Pogues at all should invalidate it.

I could have been someone
Well so could anyone
You took my dreams from me
When I first found you
I kept them with me babe
I put them with my own
Can't make it all alone
I've built my dreams around you

Oh crap. there I go... time to find a tissue.
posted by Kellydamnit at 7:39 PM on May 9, 2007 [1 favorite]

saddest Beatles song: "In My Life"

Also the best, by the way.
posted by mr_crash_davis at 7:52 PM on May 9, 2007

Whew- good thing I got here to set everyone straight!
The saddest song ever in the history of ever is "When She Loved Me", by Randy Newman in Toy Story. Yep, Toy-freakin-Story. Because, as a parent, you know that song is really about your baby growing up and not needing you and oh crap I can't even *think* about that song without losing it.

Super close second goes to "In My Life" by the Beatles- that song puts me in a weepy mood for hours.
posted by Mamapotomus at 7:57 PM on May 9, 2007

(mr crash davis and I will be over here, crying into raggedy tissues over my lack of preview.)
posted by Mamapotomus at 7:59 PM on May 9, 2007

"Desperados Waiting for a Train" -


The day 'fore he died I went to see him
I was grown and he was almost gone.
So we just closed our eyes and dreamed us up a kitchen
And sang one more verse to that old song
(spoken) Come on, Jack, that son-of-a-bitch is comin'

We're desperados waitin' for a train
Was like desperados waitin' for a train

The song was writen by Guy Clark, the version I'm linking was done by Jerry Jeff Walker.
posted by nola at 8:00 PM on May 9, 2007

Jacques Brel's "Ne me quitte pas" is the saddest song. These other tunes are just nursery rhymes by comparison.

(And nobody mentioned Joy Division?)
posted by zadcat at 8:00 PM on May 9, 2007

The saddest heavy thrash song ever written? Glad you asked:

"A Tout le Monde" by Megadeth

...
So as you read this, know my friends
I'd love to stay with you all
Please smile, smile when you think about me
My body's gone that's all

A tout le monde
A tout mes amis
Je vous aime
Je dois partir
These are the last words
I'll ever speak
And they'll set me free

Hey, if they can list Space Oddity, I can list this. At least this got banned by MTV.
posted by Pastabagel at 8:04 PM on May 9, 2007

R.E.M.'s "The Wrong Child'.
posted by jaronson at 8:05 PM on May 9, 2007

Softies, Sleep Away Your Troubles always chokes me up.
posted by Bookhouse at 8:07 PM on May 9, 2007

River of Fools by Los Lobos
Song for Kim by Concrete Blonde
Excuse me, I need to go away and cry now.
posted by found dog one eye at 8:13 PM on May 9, 2007

I forgot Joy Division.

And yeh, The Wrong Child is up there, too. In fact, Michael Stipe's voice lends itself perfectly to plaintive songs. Low springs to mind, also Half a World Away. There would have to be dozens more.
posted by UbuRoivas at 8:14 PM on May 9, 2007

The Verve - Virtual World [accoustic]. This is the song that carried me through my best friends suicide two years ago so it's got a bit of resonance with me and would drive me to tears for a year. I can't think of another band who creates that bittersweet sound so well. On Your Own, History, and A Northern Soul qualify for close seconds. History might be the best break-up song ever recorded.

Virtual World
see the water break my hand
no one knows my name, i'm not in demand

the signs are right the signs are here
who needs virtual world when i can see it now,
see it now well how how how?

No one goes
'cause no one cares
no one sees me anywhere

hey now now, hey now now my lover
whatcha gonna say?
to make this feeling fade?

she's breathing life
into known dead stars
in the dirty half-light where time means nothing at all

see the water break my fall
no one comes 'cause no one calls
have you ever seen the book
the one on my shelf
the one entitled, "self death: how to earn a million pounds"
i can see it now, oh the hearse

she's breathing down through a hole in my head
in the dirty half-light where time means nothin' at all
nothin' at all

I'm calling out for someone
anyone who'll have me
does anybody know me?
does anybody know how to cry?

what happens if i fall
what happens if i go
what happens if i come
and then i've gotta go home
posted by trinarian at 8:15 PM on May 9, 2007

No Scott Walker. Harrumph.

Some additional contenders in my book:

Bobby Vinton - Mr. Lonely
Tim Rose - Long Time Man
John Prine - Sam Stone
Bobby Darin - Artificial Flowers
Lee Hazlewood - Pour Man
Little Anthony & The Imperials - Hurt So Bad
Lambchop - Gettysburg Address
posted by ktrey at 8:15 PM on May 9, 2007

The Celtic Lament by Eugene O'Donnell.
posted by Buck Eschaton at 8:16 PM on May 9, 2007

Yet another R.E.M. - "Half a World Away".
posted by punchdrunkhistory at 8:22 PM on May 9, 2007

"Waterloo Sunset"

that's more poignant to me. Living alone but just being in the Big City, which I experienced somewhat living in Tokyo.

Speaking of which, Dreams Come True's "Namida-to Tatakatteru" (Fighting the Tears) and X Japan's "Endless Rain" will make ya sad.
posted by Heywood Mogroot at 8:24 PM on May 9, 2007

Don't Change Your Plans - Ben Folds
All My Little Words - Magnetic Fields
I Get Along Without You Very Well - as recorded by Chet Baker

This doesn't even count the songs which, although ostensibly happy, have such strong bittersweet associations in my mind that they become sad. I generally walk out of restaurants when "Don't Know Why" by Norah Jones comes on.

and the saddest springsteen song is "i'm on fire." seriously. it's the johnny cash song that johnny cash never wrote
posted by the_bone at 8:25 PM on May 9, 2007

Saddest song list without any country or blues?

Lame.
posted by Balisong at 8:28 PM on May 9, 2007

2nd Tout Le Monde.
posted by winks007 at 8:31 PM on May 9, 2007

I don't know if it is the saddest song ever. I know it is not the lyrics which are remembering a happy time but Nizlopi's JCB Song definitely belongs on the list. Tugs my heart every time I hear it.
posted by hariya at 8:32 PM on May 9, 2007

Ron Hynes. Sonny's Dream. C'est. Tout.
posted by YamwotIam at 8:33 PM on May 9, 2007

You know, I can't quite put my finger on it, but something about these comments makes me feel a bit down.
posted by davejay at 8:47 PM on May 9, 2007

Am I the only person on Metafilter who likes Amy Winehouse?
posted by jokeefe at 8:50 PM on May 9, 2007

We could make a list of the 25 saddest songs from Tom Waits alone, and it would be too short. "I'm Still Here" is the one that gets me every time.

Also, mullingitover beat me to Morphine's "Gone For Good."
posted by MrBadExample at 8:50 PM on May 9, 2007

The version of Goodbye Pork Pie Hat on Mingus Ah Um is the saddest song ever recorded.
posted by milquetoast at 8:56 PM on May 9, 2007

25 Most Exquisitely Sad Songs in the Whole English-speaking World

A bit nitpicky, but I remember some shitty "world" music awards night, in which I think Madonna or Michael Jackson was awarded "best-selling musical artist in history", totally ignoring the fact that Bollywood playback singer Lata Mangeshkar would easily have a thousand times their sales, and that's not counting the bootlegs which would make up 90% of sales.

This is obviously similarly western(anglo)-centric. The ghazal tradition (India to Persia) is very rich & melancholic, and the Armenians have sadness down to a precise artform. Arabic, greek, gypsy & flamenco music have some beautiful, sad material, and people have already commented on the lack of Francophones like Jacques Brel or Edith Piaf. The rest of the European languages are also completely unrepresented.

On top of that, you would have sad music from traditions in which we probably can't even recognise the idioms of sadness - like Chinese or a lot of African music. You could also throw in melancholy stuff that doesn't even need translation, like Ross Daly's Greek interpretations, or Eric Marchand & Thierry Robin's Bretogne / Arabic stuff. I think that jazz was completely skipped over, too, and there's a heap of bleak jazz around (thinking ECM label, in particular)

/pedantic rant
posted by UbuRoivas at 9:14 PM on May 9, 2007

Lick My Love Pump -- Spinal Tap
posted by mazola at 9:23 PM on May 9, 2007

Walking on Sunshine by Katrina and the Waves

What? The other kind of sad? Oh, OK -- ten off the top of my head:

Waking Up Alone -- Paul Williams
First of May -- Bee Gees
Georgia Lee -- Tom Waits
Ballad of Spider John -- Willis Alan Ramsey
Foggy Foggy Dew -- Sinead O'Connor
You Don't Know Me -- Ray Charles
Brothers in Arms -- Dire Straits
At This Moment -- Billy Vera & The Beaters
Exhibit 13 -- Blue Man Group
Fire and Rain -- James Taylor

And, please: Along Again Naturally? That whiny little self-absorbed poser is looking for attention, not a way out. If you want to hear someone on the edge of suicide, try When I Fall by Barenaked Ladies. "They're frightened of jumping in case they survive" "...step from this scaffold...(be) with my family and pastor and grandfather who's dead." THAT's suicidal impulse.
posted by forrest at 9:28 PM on May 9, 2007

That list is fucking TERRIBLE.
The saddest song is Dirty Three's "Lullabye for Christie."
posted by BlackLeotardFront at 9:31 PM on May 9, 2007

Artists already mentioned by others, but:

Walker Brothers - We're All Alone
Swans - God Damn the Sun
Joy Division - their entire recording career, really, but let's go for Atmosphere. Or Isolation.

Manic Street Preachers: 4st 7lb, or A Design For Life always cut me up.
posted by Infinite Jest at 9:50 PM on May 9, 2007

I third "Sometimes it snows in April".

Thinking of that song I realize what defines a real sad song: it should be almost painful to hear. It should make you think of the uselessness of it all, of time slipping by without being able to do anything about it, of your own death and of those around you. It should make your breathing heavy to a point where you almost think you are dying already.

That's what "Sometimes it snows in April" does to me (and the also mentioned "Hurt" in the Johnny Cash version + Cracker's "Big Dipper" to some degree as well).
posted by Berend at 10:17 PM on May 9, 2007 [1 favorite]

Am I the only one that thinks that number one on this list should be "The living years" - Mike and the Mechanics;

Ramix - Sad as it may be, no.
posted by Neale at 10:18 PM on May 9, 2007

Also harping on the anglocentrism, sorry: no fado... NO FADO? No tango... WHA? No cred for you!

(Not that I wouldn't also agree that things like Fiona Apple's "I Know" or Aimee Mann's "It's Not" are good enough to make the proverbial small car full of clowns bawl their eyes out, mind you... And a wink to everyone up there who seems to know where to find prosthetic glass legs full of beer. That little movie was extraordinary.)
posted by Iosephus at 10:25 PM on May 9, 2007

Yes! God Damn the Sun!

(God damn anyone that says a kind word, God damn the light it shines and this world it shows...)
posted by UbuRoivas at 10:27 PM on May 9, 2007

Yes this is really a poor list yet the Sam Cooke inclusion is rather nice also I suggest Tom Waits - "Hang Down Your Head".
posted by lone_one at 10:36 PM on May 9, 2007

The Last Song by Elton John. About a father whose son is dying of AIDS. Also used as an AIDS awareness song, specifically in And The Band Played On.

`Cause I never thought I'd lose
I only thought I'd win
I never dreamed I'd feel
This fire beneath my skin
I can't believe you love me
I never thought you'd come
I guess I misjudged love
Between a father and his son
posted by aclevername at 11:26 PM on May 9, 2007

BTW

Artist: Black Tape For A Blue Girl
Album: Remnants of a Deeper Purity

End Of Discussion
posted by nataaniinez at 11:29 PM on May 9, 2007

"Stand by your man..." *dodges beer bottles*
posted by kid ichorous at 11:36 PM on May 9, 2007

A bit nitpicky, but I remember some shitty "world" music awards night, in which I think Madonna or Michael Jackson was awarded "best-selling musical artist in history", totally ignoring the fact that Bollywood playback singer Lata Mangeshkar would easily have a thousand times their sales, and that's not counting the bootlegs which would make up 90% of sales.

This is obviously similarly western(anglo)-centric. The ghazal tradition (India to Persia) is very rich & melancholic, and the Armenians have sadness down to a precise artform. Arabic, greek, gypsy & flamenco music have some beautiful, sad material, and people have already commented on the lack of Francophones like Jacques Brel or Edith Piaf. The rest of the European languages are also completely unrepresented.

On top of that, you would have sad music from traditions in which we probably can't even recognise the idioms of sadness - like Chinese or a lot of African music.

Not "a little bit nitpicky." More like "terminally nerdy." Of course the list wasn't the world's saddest songs. They are the saddest songs that were popular in the United States. For purposes of this little contest, I couldn't possibly care less about the Greeks, the Arabs, the Portugese, the Gypsies, etc.

Yes, I am American, and as such I am fat, lazy, stupid and insular. I don't care about Armenia's sad songs. Armenia can go cry by itself, along with China, India and all them other furriners.

Oh, and all you people who posted lyrics: Stop it. A good sad song (actually a song of any kind) is a combination of lyrics and music, with the lyrics being secondary. No one reads a song. They listen to it.

So now where were we again?
posted by Charles Wilson at 11:43 PM on May 9, 2007

Can't you read?

The discussion has ended!

*throws beer bottle*
posted by UbuRoivas at 11:43 PM on May 9, 2007 [2 favorites]

"What becomes of the broken-hearted"
"Sitting on the dock of the bay"
"Angel of the morning"

"In the year 2525" (REALLY sad)
posted by Twang at 11:43 PM on May 9, 2007

Oops. Forgot:
"Shannon"
"Walk Away Renee"
posted by Twang at 11:45 PM on May 9, 2007

"Who'll Fall?" by Coil, anyone?
posted by hototogisu at 11:48 PM on May 9, 2007

Oh, Charles Wilson got in the way of the beer bottle meant for kid ichorous.

No matter, as people all over the world are rejoicing (and by "the world", I don't mean "the United States")
posted by UbuRoivas at 11:52 PM on May 9, 2007

Yeah, that list sucks.

You guys already mentioned a lot of my choices for saddest songs, but I'd like to add Shame by Smashing Pumpkins from the Adore album. Actually most of that album is pretty sad.
posted by Devils Slide at 11:57 PM on May 9, 2007

Amen to all the Harry Chapin, Joni Mitchell, Cat Stevens, and Simon and Garfunkel songs mentioned here. (I guess I'm showing my age, but those are the songs I grew up with.)

Also, Peter Gabriel, along with "Don't Give Up" wrote some other doozies, including, for me anyway, "Red Rain."
posted by lilywing13 at 12:06 AM on May 10, 2007

"Who'll Fall?" by Coil, anyone?

Oooh! Me, sir! Me, sir! I know this one!

John Balance!
posted by UbuRoivas at 12:06 AM on May 10, 2007 [1 favorite]

Shit, for a split second there I misread "Charles Wilson" as "Charles Manson," and this thread reached new highs.
posted by kid ichorous at 12:09 AM on May 10, 2007

Peter Gabriel's "Biko"
Angels of Light's "New York Girls"
Swans' "the sound"

This game is fun.
posted by hototogisu at 12:13 AM on May 10, 2007

The Flaming Lips have a lot of sad songs. Shit, Wayne Coyne's voice alone can make me get misty-eyed. Same thing with Jeff tweedy.

Oh, and no mention of Sigur Ros?
posted by Devils Slide at 12:20 AM on May 10, 2007

get
posted by Devils Slide at 12:21 AM on May 10, 2007

Damn it all, this is the thread that will never die.

Sianspheric - "The Stars Above"
Laura Viers - "Shadow Blues"
JJ72 - "October Swimmer"
Calexico - "The Black Light"
posted by nataaniinez at 12:23 AM on May 10, 2007

no mention of Sigur Ros?

Obviously, you don't speak Hopelandish.
posted by UbuRoivas at 12:26 AM on May 10, 2007

a sad list indeed.
posted by johnny novak at 12:42 AM on May 10, 2007

The Divine Comedy's "Lucy" (after Wordsworth):

She lived unknown, and few could know
When Lucy ceased to be;
But she is in her grave and, oh,
The difference to me

A slumber did my spirit seal;
I had no human fears;
She seemed a thing that could not feel
The touch of earthly years.

No motion has she now, no force;
She neither hears nor sees;
Rolled around in earth’s diurnal course,
With rocks, and stones, and trees.
posted by Scram at 12:43 AM on May 10, 2007 [1 favorite]

One more Simon & Garfunkel entry: "Sparrow"
posted by DevilsAdvocate at 12:52 AM on May 10, 2007

O.K., I'll play. The three saddest songs I know are:

Townes van Zandt - Waiting around to Die (for maximum effect watch the version on Heartworn Highways where he makes the travelling blacksmith cry)

Pogues - And the Band Played Waltzing Mathilda

Jacques Brel - Ne me quitte pas

probably add some Nick Drake, Leonard Cohen, Nick Cave and Suicide.
posted by johnny novak at 1:05 AM on May 10, 2007

pushing 300 comments and no mention of Gram Parsons? $1000 wedding!
posted by dinsdale at 1:14 AM on May 10, 2007

oh gos, yes dinsdale

that's number four in my list.

I think someone spiked my drink
posted by johnny novak at 1:17 AM on May 10, 2007

Patty Griffin has a number of contenders, including "Poor Man's House," "Moses," and "Long Ride Home." The last is about a woman burying her husband after a relationship full of "could haves." The widow, arriving home after the funeral, notes:

Headlights staring at the driveway
The house is dark as it can be
I go inside and all is silent
It seems as empty as the inside of me

It's like two people die in this song.

But if I could nominate Patty for only one song, it'd be "As Cold As It Gets." Sad, yes. Extremely. But also angry and bitter, which makes the sadness that much more hopeless. It contains gems like "blew out the light in my soul" and "you and I'll meet down below."

The Counting Crows have been mentioned and well they should; they've got quite the list of wrist-slitting ballads. But the one that always made me want to call my shrink for a Paxil refill or just seal myself in a tomb was "Raining In Baltimore."

Bob Dylan deserves mention for "Desolation Row." I mean, Cinderella as a hooker? Is there anything out there that could do a better job of crushing your spirit?

Oh, and The Indigo Girls' version of the Dire Straits' "Romeo and Juliet" could make anyone sit down and cry.
posted by Clay201 at 1:22 AM on May 10, 2007

from the sinatra canon, i nominate "it was a very good year"; all those women but none of them stuck around.

sorry, but "cat's in the cradle" doesn't make it, i always think of "the cat's in the kettle at the peking moon."
posted by bruce at 1:26 AM on May 10, 2007

Wow am I late to this thread.

23. 'No Surprises' - Radiohead (1997)

Is depressing really the same thing as sad?
Cause if it is...

Bulletproof
Fake Plastic Trees
Black Star
Exit Music (for a film)
No Surprises
Lucky
The Tourist
[hell even] Karma Police

funny. I think they've gotten happier.

my pick: no suprises (fake plastic trees and black star taking 2nd and 3rd)


A heart that's full up like a landfill
A job that slowly kills you
Bruises that won't heal

You look so tired and unhappy
Bring down the government
They don't, they don't speak for us
I'll take a quiet life
A handshake of carbon monoxide

No alarms and no surprises
No alarms and no surprises
No alarms and no surprises
Silent, silent

This is my final fit, my final bellyache with

No alarms and no surprises
No alarms and no surprises
No alarms and no surprises please

Such a pretty house, such a pretty garden

No alarms and no surprises (let me out of here)
No alarms and no surprises (let me out of here)
No alarms and no surprises please (let me out of here)

Oh, and all the Indigo Girls version of Romeo and Juliet makes me want to do is go listen to Dire Straits. Badly.
posted by dreamsign at 1:33 AM on May 10, 2007

The saddest song is the song she used to sing.
posted by pracowity at 1:52 AM on May 10, 2007

Obviously, you don't speak Hopelandish.

Ha. I know the word "Hopelandish" implies that the lyrics are positive, but Jonsi's voice, the bowed guitar, strings, and piano all combine to make their music sound very sad (and incredibly beautiful).
posted by Devils Slide at 1:58 AM on May 10, 2007

Most of Wilco's Summerteeth.

Also, Elliott Smith - guess which song I'd add to the list.
posted by betweenthebars at 2:12 AM on May 10, 2007

Sarah McLachlan, I Will Not Forget You:

I remember the nights I watched as you lay sleeping
Your body gripped by some far away dream
Well I was so scared and so in love then
And so lost in all of you that I had seen
But no one ever talked in the darkness
No voice ever added fuel to the fire
No light ever shone in the doorway
Deep in the hollow of earthly desires
But if in some dream there was brightness
If in some memory some sort of sign
And flesh be revived in the shadows
Blessed our bodies would lay so entwined

[CHORUS]

And I will oh I will not forget you
Nor will I ever let you go
I will oh I will not forget you

I remember when you left in the morning at daybreak
So silent you stole from my bed
To go back to the one who possesses your soul
And I back to the life that I dread.
So I ran like the wind to the water
Please don't leave me again I cried
And I threw bitter tears at the ocean
But all that came back was the tide...

[CHORUS]

Oh, and Nick Cave - The Kindness Of Strangers is horrifyingly sad because of the sobbing woman in the background; I literally had to turn it off the first time I heard it, and it still gives me shivers...
posted by PontifexPrimus at 2:43 AM on May 10, 2007

I had my own nominations (Sometimes in Winter—Blood, Sweat, and Tears; Moody River—Doc and Richard Watson), and my own observation about the single most heartbreaking chord I know (the f-sharp minor half-diminished 6/5 chord in Real Love—The Beatles: 'no need to be alone, no need to be alone). And I was going to soberly disagree with doctorschlock about 'Cast Your Fate', which I love.

But all that evaporated when kirkaracha mentioned the Ashokan Farewell.

Yes. Yes. Second that. Add to it (not replace it with, but add to it) another recently-written but folk-style tune about the Civil War: Two Brothers. Here it is, though I've got a lump in my throat just from trying to punctuate it:

Two brothers on their way,
Two brothers on their way.
Two brothers on their way:
One wore blue, and one wore gray.

One wore blue and one wore gray;
As they marched along their way,
The fife and drum began to play—
All on a beautiful morning.

One was gentle, one was kind;
One was gentle, one was kind.
One was gentle, one was kind;
One came home. One stayed behind.

Cannonball don't pay no mind
If you're gentle or you're kind.
It don't think on the folks behind,
Or on a beautiful morning.

Two girls wait by the railroad track,
Two girls wait by the railroad track.
Two girls wait by the railroad track:
One wears blue, and one wears black.

One wears blue and one wears black,
Waiting by the railroad track
For their lovers to come back ...
All, on a beautiful morning.

posted by eritain at 3:19 AM on May 10, 2007

Also, who the hell is Amy Winehouse

No idea either, dude.

and why exactly does every media outlet all of a sudden think I should care?

That one, I can answer.
posted by eritain at 3:32 AM on May 10, 2007

The two that always get me are Squeeze's "Up The Junction" and Freedy Johnston's "Evie's Tears".
posted by gfrobe at 3:35 AM on May 10, 2007

Love Hurts - Gram Parsons and Emmylou Harris.
posted by emf at 4:34 AM on May 10, 2007

Not mentioned, Billy Joel's "Piano Man"--nothing more sad than lost dreams, unrealized potential, and acceptance of your place in the world, as mundane as it is.
posted by BozoBurgerBonanza at 4:48 AM on May 10, 2007

Aren't there some opera arias about dying of tuberculosis/broken hearts/betrayal/being a soprano which are sadder than most of these?

Also, the Radiohead choice isn't their saddest - I find "Creep" sadder/angryer/more depressive.

But I'm glad to see Johnny Cash's version of "Hurt" on the list - NIN's is angry, but his persona has the sadness that only age and regrets can bring.
posted by jb at 5:03 AM on May 10, 2007

Actually, more seriously -- The Great Mandela, sung by Peter, Paul and Mary. Powerful and weeping.

Another list.
posted by jb at 5:09 AM on May 10, 2007 [1 favorite]

Ms Winehouse has done very well this year in the UK, and (to be fair) the production on her last album is fucking spectacular.

She doesn't belong on this list, though.

Plus, she's a complete nutjob. I'll be surprised if she lives to record another album. Drug abuse, eating disorder, bipolar: the lot. She's one shotgun and a few needles away from being the next Cobain.
posted by chuckdarwin at 5:16 AM on May 10, 2007

Plane Wreck at Los Gatos (Deportee); recorded by a large number of artists, as noted in the Wikipedia article. And at least as relevant today as it was when it was written, if not more so.

(jb's mention of "The Great Mandela" reminded me of this, as both that and "Deportee" appear on Peter Paul & Mary's LifeLines album.)
posted by DevilsAdvocate at 5:22 AM on May 10, 2007

Tom Wait's "Ruby's Arms"
Elvis Costello/Burt B "This House is Empty Now"
Gene Watson "Farewell Party"
Alan Jackson "Here in the Real World"
Dale Watson "I Hate These Songs"
Lucinda Williams, "He Never Got Enough Love"
Townes Van Zandt "Tecumseh"
posted by spitbull at 5:26 AM on May 10, 2007

oh, and Dwight Yoakam's "South of Cincinatti" b/w "I Sang Dixie"
posted by spitbull at 5:27 AM on May 10, 2007

And could it be true that Hank Williams is not represented anywhere on the list or in this thread? "Wedding Bells," "My Son Calls Another Man Daddy," or "I'm So Lonesome I Could Cry" ain't chopped liver.
posted by spitbull at 5:32 AM on May 10, 2007

spitbull, someone mentioned "I'm So Lonesome I Could Cry" way upthread. And if they hadn't, I would've!
posted by flapjax at midnite at 5:42 AM on May 10, 2007

Randy Newman - Guilty
posted by rfs at 5:47 AM on May 10, 2007

Did they leave off NIN because it was too easy? The Johnny Cash cover is nice, but I'll wager he wrote songs of his own that are sadder.

and as NIN goes (or most of anything) it's hard to beat Something I Can Never Have.
posted by Uther Bentrazor at 6:00 AM on May 10, 2007

Plus, she's a complete nutjob. I'll be surprised if she lives to record another album. Drug abuse, eating disorder, bipolar: the lot. She's one shotgun and a few needles away from being the next Cobain.

The thing that's keeping her from being "the next Cobain:" Talent.
posted by the_bone at 6:20 AM on May 10, 2007

That Country Genre has a ton of tear-jerkers. One of my favorite country anthems...Hank Jr - Knoxville Courthouse Blues. It could happen to any of us, I suppose. Fa-real!
posted by winks007 at 6:22 AM on May 10, 2007

Metafilter...our list can kick your list's ass!
posted by winks007 at 6:25 AM on May 10, 2007

I'm Still Gone by The Watchmen (who've you've probably never heard of unless you were a Teenager in the 90's in Canada).

I think it'll be a Sad Music Day here.
posted by pookzilla at 6:29 AM on May 10, 2007

What? Uh, Where Did You Sleep Last Night, anyone?
posted by mobunited at 6:58 AM on May 10, 2007

That Frank Sinatra song...but I forgot the title..
When I was 17 it was a very good year something......
posted by doctorschlock at 7:07 AM on May 10, 2007

With Biscotti I am also unanimous.

Fake Plastic Trees is n times sadder than No Surprises, where 'n' is the saddest number you can think of.

Gravity always wins.
posted by Mr Bismarck at 7:26 AM on May 10, 2007

Sarah McLachlan, I Will Not Forget You

You know, I don't tend to give her much credit anymore, but it's astounding that her voice was sharp in my mind as I reread those lyrics.

And hey, after this many comments, I guess I'm the only one who finds Seger's Against The Wind sad. Not a fan, but that song gets me every time.
posted by dreamsign at 8:08 AM on May 10, 2007

The saddest Billy Bragg song (my own personal view, obviously, and more than influenced by the fact that I played it over and over after a very sad breakup) is "Must I Paint You A Picture?" (although I don't really like the bit with the girl singing). My pillow becomes moistened just thinking about these lyrics:

And when I see you
You just turn around and walk away like we never met
Oh we used to be so brave
I dreamt the world stopped turning as we climbed the hill
I dreamt impossible dreams that we were lovers still

Sob!
posted by h00py at 8:23 AM on May 10, 2007

You guys want sad? Try:
"The Boiler" -- Rhoda Dakar
"When This Is Over" -- Hayden
"...A Psychopath" -- Lisa Germano
posted by JT at 8:24 AM on May 10, 2007

A sad song, which you have not heard:
N.Q. Arbuckle: "Darkness has fallen"

"And there'll be a time when the roses bloom again,
On misty summer mornings when we're walking home to bed.
And you can ask me forever for anything, my friend."

A sad song, which you've probably heard:
Billy Joel, Lullabye
"Someday your child will cry, and if you sing this lullabye
Then in your heart, there will always be a part of me."

The saddest song in the world:
Tom Waits, "Martha"

"Those were the days of roses,
Of poetry and prose, and Martha,
All I had was you and all you had was me."

I first heard this song at a funeral for an artist who was cut down at his prime. We were packed into the Great Hall of Hart House, if anyone here knows that space. And just like the ceremony, the song pretends to be about rememberance, when in fact every word is suffused with deep, deep regret...

"And I remember quiet evenings trembling close to you..."
posted by bicyclefish at 8:41 AM on May 10, 2007

Duk Koo Kim by Sun Kil Moon certainly deserves a spot on this list, especially when you do a little research on the back story.

watching an old fight film last night
Ray Mancini vs. Duk Koo Kim
the boy from Seoul was hanging in good
but the pounding took to him
and there in the square he lay alone
without face without crown
and the angel who looked upon
never came down
posted by Scoo at 8:43 AM on May 10, 2007

*tastes*

hmmm....needs more goth!

Type O Negative - Everything Dies, Everyone I Love is Dead, Red Water (Christmas Mourn)
The Sisters of Mercy's cover of Emma, Marian
James Ray and the Performance - Edie Sedgwick
Coil - Ostia
Killing Joke - Jana
Fields of the Nephilim - Celebrate
posted by malocchio at 8:49 AM on May 10, 2007

Aimee Mann's "Wise Up"
posted by kirkaracha at 9:03 AM on May 10, 2007

What? No "Have you ever loved a woman" by Derek & the Dominoes? Spare me!
posted by Pressed Rat at 9:23 AM on May 10, 2007

Late to the game, but have to add REM's "Try not to breathe" - I dare anyone to listen to that song and NOT collapse into a puddle of tears
posted by msali at 9:28 AM on May 10, 2007

Surely, Red House Painters' debut, the ne plus ultra of melancholy.

"the light color in the room
the sunshine seeping in
doesn't mix with the black of
death's angel looming in
i've had enough of the
brutal beatings and name callings
to lose me to this bed
bruised internally
eternally..."
posted by Rufus T. Firefly at 10:31 AM on May 10, 2007

I gotta go with Nina Simone's cover of Randy Newman's "I Think It's Going to Rain Today" (and the runner-ups are three-quarters of anything Mark Eitzel ever sang -- but for some reason I'm thinking strongly of "Western Sky").
posted by allaboutgeorge at 10:42 AM on May 10, 2007

Okay, so I don't cry at songs too often, but Badly Drawn Boy - A Minor Incident just kills me EVERY time:


I'd be a better person
On the other side I'm sure
You'd find a way to help yourself
And find another door
To shrug off minor incidents
And make us both feel proud
I just wish I could be there
To see you through
posted by lattiboy at 11:09 AM on May 10, 2007

I almost forgot the MOST depressing band in all creation, Tindersticks! Just pick a song, drive into a dark parking lot and give the fuck up. Seriously, the videos are even more depressing....
posted by lattiboy at 11:15 AM on May 10, 2007

The Band - It Makes No Difference
Sufjan Stevens - Casimir Pulaski Day
Antony And The Johnsons - Hope There's Someone
Bob Dylan - I'm Not There
Tom Waits - A Little Rain
The National - Baby We'll Be Fine
The Magnetic Fields - Grand Canyon or All My Little Words
Husker Du - Hardly Getting Over It
The Handsome Family - The Last
Uncle Tupelo - Still Be Around
Cat Power - Good Woman
Richard Buckner - 1985
Richard and Linda Thompson - Has He Got a Friend For Me
Otis Redding - I've Been Loving You
The Clash - Straight To Hell
Bonnie Prince Billy - I See a Darkness
Warren Zevon - She's Too Good For Me
Lambchop - Gettysburg Address
Patty Loveless - Here I Am
The Jam - That's Entertainment
John Prine - Sam Stone
Townes Van Zandt - Kathleen
Kenny Rogers - Ruby

And most of Leonard Cohen, Elliott Smith, and John Darnielle's discographies as the 25^th entry.
posted by Alvy Ampersand at 11:31 AM on May 10, 2007

Ray Charles "Lonely Avenue"
Ben E. King "Young Boy Blues"
Smokey Robinson & the Miracles "The Love I Saw in You Was Just a Mirage"
Smokey Robinson & the Miracles "Tracks of My Tears"
Smokey Robinson & the Miracles "I've Got to Dance To Keep From Crying"

Ol' Smokey seems a hell of a lot more conflicted than he lets on.
posted by kalimotxero at 11:54 AM on May 10, 2007

Some of those are bittersweet. Naked as We Came e.g.
(”It Was A Very Good Year” - comes to mind too)

But I’ve always found “The Unicorn” by the Irish Rovers to be the most sadly disturbing.
So, God lets the unicorns all die because they missed the boat? WTF?
Just seemed crazy to me, and when I heard it as a kid I remember seeing friendly bearded turtlenecked Christians singing it, smiling and all the kids smiling and singing along.
And I’m screaming inside “ARE YOU MAD!!!?? God just drowned all the unicorns who were splashing and playing! And we’re all happy about it?”

SINGING:
“There was green alligators and long-necked geese *smile*
Some humpty backed camels and some chimpanzees *chuckle*
Noah cried, "Close the door because the rain is falling
And we just can't wait for no unicorns" *grin*

The ark started moving, it drifted with the tide
The unicorns looked up from the rocks and they cried
And the waters came down and sort of floated them away
That's why you never see unicorns to this very day *side to side headshake*

You'll see green alligators and long-necked geese *smile*
Some humpty backed camels and some chimpanzees*chuckle*
Some cats and rats and elephants, but sure as you're born
You're never gonna see no unicorns *big grin*”


Madness. Just a horribly sad cruel song, man. Friggin’ Shel Silverstein.
posted by Smedleyman at 12:15 PM on May 10, 2007

"No Goodbyes" by Jack Lukeman. How sad a song is is often a matter of context. The context for me: a very close friend that committed suicide had Lukeman's Metropolis Blue in his CD player. "No Goodbyes" is the last song on the album. A taste:

And I won't be coming home tonight
No I won't be sleeping by your side
No goodbyes
No goodbyes

I hope "No Goodbyes" is the saddest song I ever hear.
posted by e40 at 12:20 PM on May 10, 2007

Sad = The Leader Of The Pack
Sad, sad = The tears of a clown, great song!
Sad, sad, sad = Some more Goth: Golgotha Tenement Blues
posted by winks007 at 12:31 PM on May 10, 2007

This post needs some jonmc!
posted by winks007 at 1:03 PM on May 10, 2007

I gotta second or whatever "Puff the Magic Dragon."
posted by maxwelton at 1:09 PM on May 10, 2007

I'll third Puff and Little Jackie Paper. Remember it well - along with the Seals and Croft special that used to follow it on Saturday Mornings.
posted by winks007 at 1:19 PM on May 10, 2007

Dave Mason.....We Just Disagree
posted by doctorschlock at 1:22 PM on May 10, 2007

Rolling Stones....Angie
posted by doctorschlock at 1:22 PM on May 10, 2007

Beth....Kiss
posted by doctorschlock at 1:23 PM on May 10, 2007

A dragon lives forever but not so little boys
Painted wings and giant strings make way for other toys.
One great night it happened, Jackie Paper came no more
And PUFF that mighty dragon, he ceased his fearless roar.

His head was bent in sorrow - green scales fell like rain,
PUFF no longer went to play along the cherry lane.
Without his lifelong friend PUFF could not be brave
So PUFF that mighty dragon, sadly slipped into his cave.
posted by winks007 at 1:25 PM on May 10, 2007

If you see her say hello - Dylan


If you see her, say hello, she might be in Tangier
She left here last early spring, is livin' there, I hear
Say for me that I'm all right though things get kind of slow
She might think that I've forgotten her, don't tell her it isn't so.

We had a falling-out, like lovers often will
And to think of how she left that night, it still brings me a chill
And though our separation, it pierced me to the heart
She still lives inside of me, we've never been apart.
posted by algreer at 1:57 PM on May 10, 2007

Bread...Everything I Own
posted by doctorschlock at 2:05 PM on May 10, 2007

Reader Comments
1. thay playd this at my dad was dead =(
joshua at 8:22PM on May 5th 2007

2. sad thay playd this when my dad was dead
joshua at 8:23PM on May 5th 2007

3. i want to fuck
joshua at 8:26PM on May 5th 2007

Huh.

(From the Hurt page.)
posted by churl at 3:06 PM on May 10, 2007

I forgot Lucinda Williams' cover of Nick Drake's Which Will. That's a sad, sad song. Hauntingly lovely at the same time, though.

And Richard Thompson's God Loves a Drunk.

And Maddy Prior's cover of The Great Valerio. Thompson is an abysmal font of sadness, so it seems.
posted by Devils Rancher at 3:14 PM on May 10, 2007

Old Man Old Woman by Kristy Kruger is simultaneously sad and beautiful and melancholy and all kindsa awesome. It's about the kinda love that stands the test of time and whether that's a good thing or a bad thing or what it's just there - weather-beaten, jaded, and comfy like an old shirt.
posted by ZachsMind at 3:52 PM on May 10, 2007

Ha. I know the word "Hopelandish" implies that the [Sigur Ros] lyrics are positive, but Jonsi's voice, the bowed guitar, strings, and piano all combine to make their music sound very sad (and incredibly beautiful).

OK, then. In spite of the overwhelmingly cheerful lyrics, you can't go past the final (untitled) track of the untitled album (aka 'two sausages kissing').

Now on Cat Power: Good Woman. *sniffle*

As far as Nick Cave goes, the album And No More Shall We Part is the saddest for me. The highlight might be when Kate & Anna McGarrigle chime in at the end of Hallelujah (no, not that Hallelujah):

The tears are welling in my eyes again
I need twenty big buckets to catch them in
And twenty pretty girls to carry them down
And twenty deep holes to bury them in
posted by UbuRoivas at 4:47 PM on May 10, 2007

This song always makes me tear up a little bit:

Pond - My Dog is an Astronaut Though

It's the story of Laika the Soviet Cosmonaut dog, as told by it's owner. The song tells the story of the man strapping the dog into the space capsule while she tries to lick his face. It builds to the crescendo of the main refrain "she's not comin' back!"

Not a dry eye in the house, I tells ya.
posted by psmealey at 1:34 PM on May 11, 2007

Also, if more people had any idea what it was actually about, Katrina and the Waves' Walking on Sunshine would be universally accepted as the saddest song ever written.
posted by psmealey at 1:37 PM on May 11, 2007

I didn't have time to read all the comments, so perhaps it's already been suggested, but anyone up for a super-sad tape swap? Email's in profile.
posted by 912 Greens at 9:17 PM on May 11, 2007

BRICK, by Ben Folds Five:

"Now that I have found someone
I'm feeling more alone
Than I ever have before

She's a brick and I'm drowning slowly
Off the coast and I'm headed nowhere..."

And then there's "Two Beds and A Coffee Machine" by Savage Garden (I'm so pissed that they ever broke up):

"another ditch in the road
you keep moving
another stop sign
you keep moving on
and the years go by so fast
wonder how I ever made it through

another bruise to try and hide
another alibi to write
another lonely highway in the black of night"

Futility is sad.

Edgar Allan Poe once said that the best subject for a poem was the death of a lover, as written from the perspective of the survivor (hence his, "Annabel Lee," a poem I knew by heart before I could read myself. Yes, I had that kind of strange up-bringing). He felt that this was the saddest topic that could be developed.

To me, loneliness within a relationship is the saddest.

No, I correct myself: the death of a child is absolutely the most poignant.

But loneliness is second.
posted by misha at 8:40 AM on May 13, 2007

If no one has said it yet, thanks for starting this incredible thread, by the way.
posted by misha at 8:48 AM on May 13, 2007

To me, loneliness within a relationship is the saddest.

Another great, great song with that as a theme is The The's Kingdom of Rain. It's a duet with Sinéad O'Connor on Mind Bomb.
posted by psmealey at 9:32 AM on May 13, 2007

Richard Thompson's Dimming of the Day.

I love the version sung by David Gilmour on his DVD.

This old house is falling down around my ears
I'm drowning in a river of my tears
When all my will is gone you hold me sway
I need you at the dimming of the day
posted by The Deej at 11:58 AM on May 13, 2007

Deej--
Nice find!
Ol' Dave is The Shit.
He must be 44,000 years old by now.
Rave on, David.
posted by Dizzy at 2:26 PM on May 13, 2007

Since Poe and Bob Dylan have both come up in this thread, how many folks out there know that the title for Bob's excellent "Time Out of Mind" release (which has a goodly number of exquisitely sad songs on it) was taken from Poe's short story, The Fall of the House of Usher"?
posted by flapjax at midnite at 4:34 PM on May 13, 2007