What are the saddest songs ever?

November 16, 2004 6:34 AM

What are the saddest songs ever?

The ones that really do it for me are REM's "Everybody Hurts" and the Donnie Darko song. Those are pretty similar, but I'm looking for suggestions from any genre, style, time period or degree of maudlinness so long as they're crushingly depressing.

posted by moift to Grab Bag (98 answers total)

What about "Someone To Pull The Trigger" by Matthew Sweet or "When U Were Mine" by Prince?
posted by emptybowl at 6:38 AM on November 16, 2004

"Patches" by Clarence Carter.

"Live Forever" by Billy Joe Shaver.

"In my Room" by the Beach Boys. "Coat Of Many Colors" by Dolly Parton.

I don't know if sad is even the word but they all make me weepy every time.
posted by jonmc at 6:45 AM on November 16, 2004

A Letter to Elise, The Cure. I spent one very depressed summer in a shithole studio apartment listening to that song on repeat. Which didn't help.
posted by sugarfish at 6:50 AM on November 16, 2004 [1 favorite]

Cat Stevens - Cat's Cradle
posted by banished at 6:53 AM on November 16, 2004

That's Harry Chapin, banished.
posted by jonmc at 6:58 AM on November 16, 2004

strange fruit?
if we're talking about personal loss, "they can't take that away from me" always makes me shiver, too (both billie holiday, which may be glaringly obvious, but might not be for some, i dunno).
posted by andrew cooke at 6:59 AM on November 16, 2004

Sun Kil Moon - Carry Me Ohio
posted by damnitkage at 6:59 AM on November 16, 2004

And also "First Cut Is The Deepest" any version except for Cheryl Crow's and Chris Farlowe's version of "Handbags & Gladrags."
posted by jonmc at 6:59 AM on November 16, 2004

"Am I Blue?" Lyrics by Grant Clark Music by Harry Akst
posted by riffola at 7:01 AM on November 16, 2004

I was gonna say "Fire and Rain," but "Cat's Cradle..." *sniff*
posted by Tubes at 7:02 AM on November 16, 2004

"You Are My Sunshine".
posted by ed\26h at 7:02 AM on November 16, 2004

OK Computer has a number of solemn songs that I really like when I'm sad.
posted by gramcracker at 7:09 AM on November 16, 2004

The "song" form is a little distorted in this case, but if you want to venture, try this Silver Mt. Zion record -- Movie (Never Made) [mp3] is a realllll bummer. Related: Godspeed You Black Emperor!'s The Dead Flag Blues [mp3]. More mp3 excerpts.
posted by RJ Reynolds at 7:12 AM on November 16, 2004

Look up the recent "break-up" songs thread.
posted by agregoli at 7:16 AM on November 16, 2004

Haven't we been through this already? Richard Thompson's Small Town Romance. If I were at home I could come up with a much longer list, I'm sure.
posted by kenko at 7:17 AM on November 16, 2004

Holly Cole Trio's "Blame it On My Youth" (the song, not the album).
posted by orange swan at 7:19 AM on November 16, 2004

"Oh Comely" by Neutral Milk Hotel
"Bankrupt on Selling" by Modest Mouse
posted by saladin at 7:20 AM on November 16, 2004

The first ones that come to mind:
American Music Club - The Confidential Agent
Richard Thompson - How Will I Ever Be Simple Again
Sarah McLachlan - Angel
The Swans - Goddamn the Sun
Jane Sibbery - The Walking (and Constantly)

Nearly the entire songbook of The Cowboys Junkies.
posted by vers at 7:28 AM on November 16, 2004

"Someday Never Comes" - Creedence Clearwater Revival
posted by SPrintF at 7:29 AM on November 16, 2004

"The Band Played Waltzing Matilda." The Pogues version is good.
posted by transient at 7:30 AM on November 16, 2004

Julie Miller's "I Still Cry" (lyrics) wasn't sad to me until after September 11, when I realized it is an elegy to someone who died in September, even though, oddly, it predates 9/11.

Michelle Shocked "A Child Like Grace" (lyrics) is about losing a four-year-old child.
posted by stupidsexyFlanders at 7:30 AM on November 16, 2004

Headlights on the Parade by the Blue Nile
Sometimes it Snows in April by Prince
Drowned by The Who
posted by ba at 7:31 AM on November 16, 2004

130 years after his great grandfather left the small village of Kilkelly in County Mayo Ireland, Peter Jones found a bundle of letters sent to his great grandfather by his great grandfather's father in Ireland. The letters tell of family news, births, death, sales of land and bad harvests. The letters were used to write the following song.
Lyrics to Killkelly.
Always makes me cry.
posted by kenaman at 7:31 AM on November 16, 2004

...someone who died in September, even though, oddly, it predates 9/11

That's not so odd. Most Septembers predated 9/11.
posted by ba at 7:32 AM on November 16, 2004

Eagles: The Last Resort
posted by yoga at 7:36 AM on November 16, 2004

Gloomy Sunday was reputed to have caused several suicides.
posted by Acetylene at 7:40 AM on November 16, 2004

Most of the songs on Cure's Disintegration album--especially the second half ("Last Dance, "Same Deep Water as You," etc.)--are exquisitely sad. As are many songs penned by Stephin Merritt; "Busby Berkeley Dreams" on 69 Love Songs comes to mind, but there are lots of others that explore specific kinds and instances of sadness.
posted by arco at 7:41 AM on November 16, 2004

"Bottomless Cup" and "Sound of Lies", both by the Jayhawks.

and ed\26h is right, "You Are My Sunshine" is brutal if you listen to all the words.
posted by COBRA! at 7:43 AM on November 16, 2004

Tom Waits - Cold, Cold Ground

Jeff Buckley - Hallelujah

Ken Burn's Civil War miniseries - Ashokan Farewell/Sullivan Ballou Letter

The missus (still waiting for those signups!) writes in:

Shawn Colvin - Twilight

Billy Bragg & Wilco - One by One
posted by robocop is bleeding at 7:44 AM on November 16, 2004

Don't Think Twice, It's Alright [Dylan and others]

Flint (For the Unemployed and Underpaid) by Sufjan Stevens pushes all my pathos buttons.

Since the first of June
lost my job
and lost my room
I pretend to try
Even if I try alone
...
refrain: I'll do anything for you
I'll do anything for you
I did everything for you
I did everything for you

There's a lot of traditional songs that have really gripping lyrics that can be really sad with the right singer. Dave Van Ronk's version of House Carpenter and Sinead O'Connor's rendition of Butcher Boy
posted by jessamyn at 7:53 AM on November 16, 2004

Luka - Suzanne Vega (I find this a very hard song to listen to, even though the beat seems uptempto)
10,000 Miles - Mary Chapin Carpenter (it's her voice that makes it sad, the lyrics are borderline hopeful)
Fire and Rain - James Taylor
Left and Leaving - The Weakerthans
Winter, I Can't See New York - Tori Amos
On Every Corner, JukeBox - Ani DiFranco
posted by nelleish at 7:53 AM on November 16, 2004

Elvis Costello's cover of "The End of the Rainbow" and Johnny Cash's cover of "Hurt".
posted by amarynth at 7:54 AM on November 16, 2004

Train Song, by Tom Waits. The lyrics are definitely sad, but more so than that, his vocal delivery is just crushing.

Also, The Magnetic Fields' I Don't Believe in the Sun.
posted by fletchmuy at 7:56 AM on November 16, 2004

"It's quarter to three,
There's no one in the place 'cept you and me
So set 'em' up Joe
I got a little story I think you oughtta know

We're drinking my friend
to the end of a brief episode
So make it one for my baby
And one more for the road."
posted by GaelFC at 7:58 AM on November 16, 2004

A Thousand Paper Cranes, Mono
posted by four panels at 8:00 AM on November 16, 2004

Paradise by John Prine
posted by TedW at 8:06 AM on November 16, 2004

Pocahontas by Neil Young
posted by picea at 8:08 AM on November 16, 2004

Lightening Crashes by Live is depressing.
posted by evening at 8:10 AM on November 16, 2004

-Hurt by Nine Inch Nails/ Johnny Cash
What have I become
My sweetest friend
Everyone I know goes away
In the end
And you could have it all
My empire of dirt
I will let you down
I will make you hurt

-Famous Blue Raincoat- Leonard Cohen (always gets me. even if it's kind of a positive song at the same time...)
And you treated my woman to a flake of your life
And when she came back she was nobody’s wife.

Most of Jeff Buckley's stuff is pretty damn sad too.
posted by degnarra at 8:16 AM on November 16, 2004

Scanning my playlist:

- Anything on Chris Isaak's Forever Blue album. Graduation Day, Wicked Game, Go Walking Down There, Forever Blue...

- "Sing Me To Sleep" by the Smiths

- "What a Good Boy" by Barenaked Ladies

- "Eclipse" and "Rhymes and Reasons" by John Denver

- "It Ain't Me Babe," "A Hard Rain's Gonna Fall," "Hollis Brown," "Don't Think Twice It's All Right" by Bob Dylan

- "And So It Goes" by Billy Joel

- "For Lovin' Me" by Gordon Lightfoot

- "Changes", "Crucifixion" and "There But For Fortune" by Phil Ochs

- "Cold Blue Steel and Sweet Fire" by Joni Mitchell

- "If I Wrote You" by Dar Williams

- "Needle and the Damage Done" by Neil Young
posted by PrinceValium at 8:22 AM on November 16, 2004

"Baby Mine" from Dumbo

If you are not on the floor sobbing from the love between cartoon elephant mother and child, you are a cold cold human being.
posted by stefnet at 8:22 AM on November 16, 2004 [2 favorites]

MacArthur Park Richard Harris (not the Donna Summer remake)
All that sweet green icing flowing down.
[sob]
posted by TimeFactor at 8:28 AM on November 16, 2004

I was going to say "Bright Eyes" by Art Garfunkel, but I think I have to agree with stefnet.
posted by briank at 8:29 AM on November 16, 2004

."explain" - jeremy enigk
."have you forgotten," "song for a blue guitar," "katy song," "take me out," "24," "medicine bottle," the simon and garfunkel cover "i am a rock," "brockwell park," "moments," "drop" "smokey," "michigan," "trailways," "ruth marie" (under mark kozelek's solo name, i believe) - red house painters
."the only moment we were alone" - explosions in the sky
."a single wish" - this mortal coil
."holocaust" - both big star's and the this mortal coil cover
."damage" - yo la tengo
."poker night" - sarah white
."i've been a mess" - american music club
."midway park" - whiskeytown
."annabelle" - gillian welch
posted by ifjuly at 8:31 AM on November 16, 2004

Rebekah del Rio's cover of Elvis Costello's "Crying." It's an a capella recording called "Llorando" and it's from Mulholland Drive. (That link is a pretty low-res copy that doesn't really give you the songs in its full force.

Any version of "She Thinks I Still Care."

"Baby Mine," for sure.
posted by blueshammer at 8:36 AM on November 16, 2004

"Last Kiss" -- Pearl Jam

"Exit Music (For a Film)" -- Radiohead
posted by pardonyou? at 8:36 AM on November 16, 2004

"Ruby's Arms" - Tom Waits
posted by transient at 8:38 AM on November 16, 2004

Response by poster: Thanks for the comments. There are a lot of excellent suggestions here that I'd forgotten about and a lot of things that hadn't even occurred to me. I'd post happycat now but I can't find him. :(
posted by moift at 8:39 AM on November 16, 2004

Assuming we're going for just "sad" mood songs and not outright depressing ones (those were in the breakup music thread):

Midnight Oil's version of "In The Valley" from MTV Unplugged is easily the saddest song I've ever heard. Worth looking up even if you're not into the Oils.

Peter Gabriel's piano-only version of "Here Comes The Flood" is also right up there... not so the original. "Don't Give Up" definitely qualifies as very sad, too.

Others:

Channel Light Vessel's "Bill's Last Waltz"
Dan Fogelberg's "Same Old Lang Syne"
Howard Jones's "No One Is To Blame"
Lisa Loeb's "How"
Kate St. John's "On The Bridge"

On preview: second the Billy Joel and Suzanne Vega mentions.
posted by frallyth at 8:43 AM on November 16, 2004

"Honey" by Bobby Goldsboro. The angels came and took her away!
posted by Mayor Curley at 8:45 AM on November 16, 2004

My wife says all the music I listen to is depressing. Here's some of my favorites:

Elvis Costello - The Birds Will Still Be Singing (from The Juliet Letters)
Eels - Electroshock Blues (The whole album really)
Nick Cave - Idiot Prayer (from The Boatman's Call)
Tom Waits - Georgia Lee (Mule Variations)
The Pogues - The Old Main Drag (Rum, Sodomy and the Lash)
Lou Reed - The Bed /The Kids / Sad Song (from Berlin)
Tindersticks - Cherry Blossoms (from 2nd Album)
Johnny Cash - Drive On (from American Recordings)
Leonard Cohen - Joan of Arc (among many others from Songs of Love and Hate)
posted by Kafkaesque at 8:52 AM on November 16, 2004

song for a dead friend by kevin gilbert.
posted by modge at 8:53 AM on November 16, 2004

This One's Gonna Bruise - Beth Orton


According to New Music Express the top 10 morose albums are:

1. "Sister Lovers" - Big Star
2. "Closer" - Joy Division
3. "Ladies and Gentlemen We Are Floating In Space"- Spiritualized
4. "In Utero" - Nirvana
5. "Songs Of Love And Hate" - Leonard Cohen
6. "Lady In Satin"' - Billie Holiday
7. "In The Wee Small Hours" - Frank Sinatra
8. "Pink Moon" - Nick Drake
9. "Bubble And Scrape" - Sebadoh
10. "Unknown Pleasures" - Joy Division
posted by m@ at 8:54 AM on November 16, 2004

Damn, I forgot some.

The second movement of Beethoven's 7th Symphony is a real heartbreaker.

Chopin's got some very poignant stuff as well, like-
Op. 63Iii C#m Mazurka
Nocturne #19 in Em Op. 72 #1
and pretty much anything else he ever wrote in a minor key.

Also, the second movement of Mozart's A major Piano Concerto no. 23 tears me up every time.
posted by saladin at 8:57 AM on November 16, 2004

Commander Cody's "Down to Seeds and Stems Again Blues"
posted by maurice at 8:58 AM on November 16, 2004

Not to mention Lick My Love Pump. It's in the saddest key, you know.
posted by Kafkaesque at 8:58 AM on November 16, 2004

-Famous Blue Raincoat- Leonard Cohen (always gets me. even if it's kind of a positive song at the same time...)
And you treated my woman to a flake of your life
And when she came back she was nobody’s wife.
posted by degnarra at 8:16 AM PST on November 16

Man, I second that! What could be sadder than the idea you still want to be friends with someone who screwed and then dumped your wife?

I have a CD I burned entitled "Ballads For a Rainy Day" which includes Famous Blue Raincoat as well as:

Georgia Lee by Tom Waits about a run away girl who dies.

Kentucky Avenue by Tom Waits which is a love song froma young boy to a young girl who is wheelchair bound.

Where the Wild Roses Growby Nick Cave, which is a duet between a murder victim and her murderer.

Mary Brown by Dave Alvin, which is about a man being duped into murder by the woman he loves.
posted by Secret Life of Gravy at 9:00 AM on November 16, 2004

Johnny Cash's cover of U2's "One"
Lynyrd Skynyrd, "Tuesday's Gone"
posted by kirkaracha at 9:26 AM on November 16, 2004

"Nickel Under the Foot" from The Cradle Will Rock, but not P.J. Harvey's cover version which is more angry than hopeless.
posted by PinkStainlessTail at 9:53 AM on November 16, 2004

Send in the clowns - Frank Sinatra
posted by jasondigitized at 10:03 AM on November 16, 2004

"I Remember Me" by The Silver Jews.

it's the only tune to ever make me cry. instant message "robot parker" for an mp3.
posted by mcsweetie at 10:12 AM on November 16, 2004

"history of us" - indigo girls
posted by grateful at 10:18 AM on November 16, 2004

Try a Boulevard of Broken Dreams album.
posted by rushmc at 10:21 AM on November 16, 2004

Among others already mentioned (esp. "Exit Music for a Film" and "Oh Comely"): "Goodnight Lover" by Songs Ohia
posted by jennyb at 10:22 AM on November 16, 2004

Cripes, just reading the lyrics to "Goodnight Lover" chokes me up.
posted by jennyb at 10:25 AM on November 16, 2004

"Sorrow" by Pink Floyd? Kind of an obvious title, but... it's a real downer

The sweet smell of a great sorrow lies over the land
Plumes of smoke rise and merge into the leaden sky:
A man lies and dreams of green fields and rivers,
But awakes to a morning with no reason for waking
posted by kindall at 10:32 AM on November 16, 2004

Townes Van Zandt, Tecumeseh Valley
Tonight's the Night (Neil Young, entire album)
posted by stupidsexyFlanders at 10:32 AM on November 16, 2004

The posthumous Townes van Zandt album Acoustic Blue is good for being sad.
posted by kenko at 10:44 AM on November 16, 2004

No words, but Dexter's Tune off the "Awakenings" soundtrack captures sadness pretty well. IIRC, it's what's playing during Leonard's last dance with his girlfriend...

Cohen's Hallelujiah, especially as performed by Jeff Buckley, usually gets me every time.
posted by weston at 10:54 AM on November 16, 2004

Oh, and Dead Man Walking by Bruce Springsteen. This whole CD is great if you are in a pensive mood, but especially the tile song:

There's a pale horse coming
And I'm going to ride it
I'll rise in the morning with my fate decided
A dead man walking.

I've got my story, mister
No need for you to listen
I'm just a dead man talking

I love songs with a story. One of my favorites that has a heart-breaker of a story actually has an upbeat tempo and a happy ending--Strawberry Blonde by Ron Sexsmith. It is the singer's memories of his crush on a girl from his childhood "not the girl next door, but the girl from around the corner (one of my favorite phrases) who kept her troubles to herself, but had a mother who had "lost her will." One day the mother dies and the girl disappears from the singer's life. Years later he sees her on the bus with her own daughter.

Chopin's got some very poignant stuff as well

Especially if you know some of the background. He wrote my favorite, (Prelude 15, op. 28 Raindrop) which he wrote after running away with George Sand to the island of Majorca. The love affair turned sour and it rained constantly. The music is so heartbreakingly filled with despair.
posted by Secret Life of Gravy at 10:55 AM on November 16, 2004

Nick Cave's "Ship Song".

The Replacements "Answering Machine".

The Smiths "I Know It's Over".

If anyone needs me, I'll be crying in a bubble bath.
posted by padraigin at 11:17 AM on November 16, 2004

I used to think that it doesn't get any sadder/depressing that Death Letter by White Stripes. But I just went off searching for lyrics and discovered that it was actually a cover of the original by Son House. Looks like the White Stripes' version is actually milder. Here are the Son House lyrics. It helps if you have heard at least one version of this song first so you can get a feeling of the blues chord progression used, which really adds to the mood.
posted by blindcarboncopy at 11:51 AM on November 16, 2004

I could probably listen to "Eleanor Rigby" a thousand times and still get choked up with every spin. And speaking of weepy Beatles tunes, I must admit that "Yesterday" still gets to me, as do "In My Life," "She's Leaving Home," and (somewhat weirdly, I know) "Long, Long, Long." The uber-sentimentalism of "The Long and Winding Road" occasionally gets to me as well, but only when I'm slightly drunk and feeling wistful over one or two particular exes.

On a different note entirely, Albinoni's Adagio in g minor (used to great effect in Gallipoli) pretty much makes me want to die a very romantically tragic death.

On preview, blindcarboncopy's mention of old blues/traditional songs reminds me of the sheer heartbreak of "Where Did You Sleep Last Night (In the Pines)," performed by Leadbelly, Nirvana, Dolly Parton, et al.

My girl, my girl, where will you go
I'm going where the cold wind blows
In the pines, in the pines
Where the sun don't ever shine
I would shiver the whole night through
posted by scody at 12:00 PM on November 16, 2004

Oops, forgot to include the link to this article about the history of "Where Did You Sleep Last Night," published following Cobain's suicide.
posted by scody at 12:05 PM on November 16, 2004

"the song is you".

but seriously, folks, 75 comments into the thread and no love for "gloomy sunday"?
posted by pxe2000 at 12:12 PM on November 16, 2004

also, pretty much any song by the band that richard manuel sings. (i'm partial to "whispering pines", m'self.)
posted by pxe2000 at 12:14 PM on November 16, 2004

Coldplay: "The Scientist"

Also, Cat Stevens did not write or perform "Cat's in the Cradle.
posted by grouse at 12:17 PM on November 16, 2004

Louise by Leo Kottke
Albinoni's Adagio
Auschwitz-Birkenau from Schindler's List
posted by joaquim at 12:22 PM on November 16, 2004

"Preciso Dizer Que Te Amo" - Cazuza. The first link contains a stream of the song.
posted by snez at 12:28 PM on November 16, 2004

• Peter Paul & Mary - Leavin' on a Jet Plane
• Dan Fogleberg - Go Down Easy
• The Eagles - Desperado
• [written by Woody Guthrie, recorded by many different people and groups] - Deportee (Plane Wreck at Los Gatos)
• Gordon Lightfoot - The Wreck of the Edmund Fitzgerald
• Wish You Were Here - Pink Floyd
• Lara Fabian - For Always (from A.I.)

Seconds to:

• Baby Mine (from Dumbo)
• Cat's Cradle - Harry Chapin
• Eleanor Rigby - The Beatles
• She's Leaving Home - The Beatles

And some classical entries:

• Wagner - Siegfrieds Trauermarsch [Siegfried's Funeral March] (from Götterdämmerung)
• Schubert - Erlkönig
• Mozart - Ave Verum Corpus
• Elgar - Cello Concerto
• Lloyd Weber - Pie Jesu (from Requiem)
• Barber - Adagio for Strings

The second movement of Beethoven's 7th Symphony is a real heartbreaker.
Interesting--to me that falls into the "solemn but not sad" category. It exudes too much, um, "pride" (for lack of a better term) to come across as sad to me.
posted by DevilsAdvocate at 1:20 PM on November 16, 2004

winona - come some rainy day
posted by rhapsodie at 1:44 PM on November 16, 2004

any song by the band that richard manuel sings.

Or even one Rick Danko sings: It Makes No Difference

I love you so much that it's all I can do
just to keep myself from telling you

[I know I clipped that but I prefer it this way]
posted by stupidsexyFlanders at 1:45 PM on November 16, 2004

Jerry Butler - Need to Belong
posted by dhoyt at 1:52 PM on November 16, 2004

"Love will tear us apart" - Joy Division
posted by davehat at 2:30 PM on November 16, 2004

I can't believe no one's referenced this movie yet...
posted by Gortuk at 3:13 PM on November 16, 2004

Gordon Lightfoot - Circle of Steel (a nice, depressing, Christmas-time song)
Matthew Good Band - Running for Home (the delivery does it on this one) or Man of Action
posted by oaf at 4:24 PM on November 16, 2004

Suzanne Vega's "The Queen and the Soldier"
From Les Miserables, "A Little Fall of Rain" Caveat: I'm pregnant and moody, and was playing this on my iPod while driving to visit my mother. By the time I got into my home town I was bawling my eyes out. I'm a hormonal wreck. :)
posted by tracicle at 4:24 PM on November 16, 2004

pxe2000: Acetylene already did.
posted by abcde at 4:42 PM on November 16, 2004

OK, I posted Richard Marx Hazard before, but apparently Matt didn't think it was sad enough.

He's WRONG.
posted by mr_crash_davis at 5:13 PM on November 16, 2004

Blemish by David Sylvian.
posted by kenko at 5:27 PM on November 16, 2004

see: Morrissey
posted by krunk at 5:59 PM on November 16, 2004

I See a Darkness by Bonnie 'Prince' Billy
posted by tomharpel at 6:03 PM on November 16, 2004

"Will the Circle Be Unbroken" - The Staple Singers (please, accept no substitutes)
"I Am Stretched on Your Grave" - Kate Rusby (again, sorry Sinead)
"It's So Hard to Say Goodbye to Yesterday" - Boyz II Men (I don't know why you people always insist on looking at me funny)
"Mother's Pride" - George Michael
"Full of Grace" - Sarah McLachlan
"Go Rest High on That Mountain" - Vince Gill
"Fake Plastic Trees" - Radiohead
"Winter" - Tori Amos
posted by grrarrgh00 at 6:27 PM on November 16, 2004

Jeff Buckley's Lover, You Should've Come Over:

Looking out the door I see the rain fall upon the funeral mourners
Parading in a wake of sad relations as their shoes fill up with water
And maybe I’m too young to keep good love from going wrong
But tonight you’re on my mind so you never know

When I’m broken down and hungry for your love with no way to feed it
Where are you tonight, child you know how much I need it
Too young to hold on and too old to just break free and run

Destroy's me upon every listening. Whenever I hear "Parading in a wake of sad relations as their shoes fill up with water" it just sounds like a premonition of his drowning. I need a drink now.
posted by donovan at 7:18 PM on November 16, 2004

I second American Music Club's "The Confidential Agent" and would add "Apology for an Accident" by them as well.
Jacques Brel's "Les Desesperes" kill me, even though I don't understand French.
Swans "God Damn the Sun" is almost amusing as it get worse with each verse.
"Overcast" by Mitch Froom and Ron Sexmith
"That Joke Isn't Funny Anymore" by The Smiths
"I Don't Want to Hear It Anymore" as sung by Jerry Butler is a killer.
posted by black8 at 3:26 AM on November 17, 2004

'In Tall Buildings' by John Hartford -- sung brilliantly by Gillian Welch on this otherwise forgettable album -- about a wasted life spent working for a large corporation.

Almost anything by Gillian Welch, particularly some of her more recent, more personal songs -- 'Time the Revelator' (from the album of that name) is desperately sad, even though I'm not sure what it's about, and there is another song which I have heard her sing in concert -- not recorded yet, but the working title seems to be 'The Way It Will Be' -- also rather enigmatic, but seems to be reflecting on a failed relationship.

'I Think It's Gonna Rain Today' by Randy Newman, sung by Judy Collins.

Almost anything by Billie Holiday -- 'I Cover the Waterfront' comes to mind -- and there is a particular poignancy about the later recordings, where you can hear her voice starting to deteriorate.

Dido's lament from Henry Purcell's Dido and Aeneas -- the dying woman desperately begging 'remember me .. but ah! forget my fate', remember me as I was, not as I am. I heard this sung at the funeral of a dear friend who died very cruelly of AIDS. Now I can hardly bear to listen to it.

Poems from A.E. Housman's A Shropshire Lad set to music by George Butterworth and others less well known, e.g. C.W. Orr's setting of 'Into my heart an air that kills'.

John Ireland's anthem, Greater Love Hath No Man.

Finally, the Russian Contakion for the Departed -- 'Dust thou art and unto dust shalt thou return. All we go down to the dust, and weeping o'er the grave we make our song.'
posted by verstegan at 3:54 AM on November 17, 2004

anything played in D minor - it's the saddest of all keys, makes people weep instantly.
posted by triv at 5:02 AM on November 17, 2004

The field is already too crowded to add more, but I will say that the recommendations for

Silver Jews - "I Remember Me"

and

Bonnie "Prince" Billy - "I See a Darkness"

are awesome.
posted by themadjuggler at 6:52 AM on November 17, 2004