i need more sad songs

May 8, 2006 10:42 PM

i need more suggestions on the saddest songs

i've gone through all my sad music, i've gone through suggestions posted here and here and i need more.

posted by grafholic to media & arts (92 comments total)

Try some Pedro the Lion, specifically "The Poison" and "June 18, 1976"
posted by disaster77 at 10:52 PM on May 8, 2006

Tori Amos "Winter"
Laura Veirs: "Rapture"
Radiohead: "How to Disappear Completely"
Sarah Mclachlan: "Angel"
Mono: "A Speeding Car"
Sole: "Pawn in the Game Part 2"
The Umbrella Sequence: "And Now We're Famous Writers"
Blind Melon: "Mouthful of Cavities"
Johnny Cash: "Hurt"
Miranda Sex Garden: "Gush forth my tears"
Deftones: "Change"
The Smashing Pumpkins: "Jupiter's Lament"
Eva Quartet: "Zora se Zazorila"
posted by fake at 10:53 PM on May 8, 2006

The Beautiful South - Sail This Ship Alone.

well, it gets me every time....
posted by pompomtom at 10:54 PM on May 8, 2006

Isolde's last aria in Tristan und Isolde.
posted by Captain_Tenille at 10:55 PM on May 8, 2006

Red House Painters - Another Song For A Blue Guitar

Anything by the Red House Painters is depressing, they even turned out a really sad version of Silly Love Songs by Paul McCartney & Wings.
posted by Mijo Bijo at 10:57 PM on May 8, 2006

oops... ignore me.

At least I'm consistent, I suppose...
posted by pompomtom at 10:58 PM on May 8, 2006

I've always thought Soltero's "Digging" was the saddest song I've ever heard, but (1) it's hard to find and (2) it probably helps if you've lived in Allston, where the song is set.
posted by occhiblu at 10:59 PM on May 8, 2006

Oh yes, and Red House Painters. I have Ocean Beach, and the entire album seems to be about the slow painful demise of a long-term relationship.
posted by occhiblu at 11:01 PM on May 8, 2006

The Tear Garden - Ascension Day
posted by re.becca at 11:04 PM on May 8, 2006

Boom Bip: The Matter (of Our Discussion)
Alias: Angel of Solitude
Kid Koala: Basin Street Blues
Arovane: The Storm
posted by aubilenon at 11:07 PM on May 8, 2006

There's a Mountain Goats song that rarely fails to depress called "No Children". Every word bites. Every verse stings.

I hope I cut myself shaving tomorrow.
I hope it bleeds all day long.
Our friends say it's darkest before the sunrise,
We're pretty sure they're all wrong.
I hope it stays dark forever
I hope the worst isn't over
I hope you blink before I do
I hope I never get sober.
posted by EatTheWeak at 11:07 PM on May 8, 2006 [1 favorite]

thanks everyone - keep 'em coming because i'm probably not going to sleep anytime soon.
posted by grafholic at 11:08 PM on May 8, 2006

Feist -- Let It Die (live)

He's Dead, Sleeping Pills, The Living Dead, Oceans -- all by Suede. Think dark, syrupy, somber, sensuous, sad.

The Cure - Pictures of You

DNTEL - Last Songs


And if out of these, you listen to just one -- make it Are You Going With Me?, by Pat Metheny.

all links go to mp3s from blogs or so -- none are mine.
posted by provolot at 11:15 PM on May 8, 2006

She's Leaving Home - The Beatles
posted by jimmythefish at 11:15 PM on May 8, 2006

Ooh, I hope you don't overdo it on the sad songs... off the top of my head, Sloan's "Are you giving me back my love" is incredibly sad... ("I'm singing my heart out/But you were so out of range"). You could also try their song "The Other Man" off the same album (depending on your situation...)
posted by rmm at 11:16 PM on May 8, 2006

Marking best answers in a saddest songs thread (especially one so young) seems just a little off to me.
posted by fake at 11:18 PM on May 8, 2006

A few I can think of
dire straits- romea and juliet
dire straits- tunnel of love
The whitlams -no aphrodisiac - this is awesome
the whitlams- charlie no. 3
radiohead - that last song on the end of kid A..
posted by phyle at 11:18 PM on May 8, 2006

Lou Reed -- any song off "Berlin," especially "The Kids."
Warren Zevon -- "Please Stay."
Bruce Springsteen -- "Nebraska," also take your pick.
Joy Division -- virtually any song. Start with "Isolation," "Atmosphere" and the poppy "Love Will Tear Us Apart."
Nick Drake -- "Pink Moon," "Parasite," numerous others.
Joni Mitchell -- "Blue."
Leonard Cohen -- "Bird on a Wire," "Suzanne," "Everybody Knows," many others.
Elliott Smith -- again an oevre with lots of sadness, starting with "Needle in the Hay."
Big Star -- "Holocaust."
Nirvana -- lots of sad there. "All Apologies."
The Smiths -- ehem.
Radiohead -- "Creep."
Manic Street Preachers -- "Scream to a Sigh."
Pearl Jam -- "Jeremy."
The Velvet Underground -- "Heroin."

Just a few "classics" that spring to mind. But one can really go on and on.
posted by drpynchon at 11:22 PM on May 8, 2006

"Friend to the Friendless" & "Trains"
--The World/Inferno Friendship Society
posted by Brainy at 11:33 PM on May 8, 2006

Marking best answers in a saddest songs thread (especially one so young) seems just a little off to me.

well it's rather a selfish marking - suggestion on songs that made me weep but in the end i know will make me smile when i see the sun coming up tomorrow morning. i just need to get this out of my system so i can go on.
posted by grafholic at 11:33 PM on May 8, 2006

Damien Rice - Cheers Darlin'
Natalie Merchant - Frozen Charlotte
Cake - Friend Is A Four Letter Word
The Pogues - The Band Played Waltzing Matilda
Elvis Costello - Indoor Fireworks & A Good Year For the Roses
Warren Zevon - Back in the High Life Again & Hostage-O
posted by Tenuki at 11:35 PM on May 8, 2006

Somebody Loan Me a Dime by Fenton Robinson. Not just the words, but the guitar and voice.

Honestly, there is a world of sad songs out there, many in the blues world, that you never hear suggested on metafilter. No offense, but jeremy isn't a classic.

Check out buddy guy, b.b. king, skip james if you want true classics. That's just a few well known artists. If you take the time to really dig into their library, you'll be amazed. If you don't have the time, or don't want to put in the effort, stick with popular music.
posted by justgary at 11:39 PM on May 8, 2006

The Kinks' "Waterloo Sunset" is the most sublimely sad pop song I've ever heard. There's a short sample of it here.
posted by maryh at 11:41 PM on May 8, 2006

Jim Croce - Photographs & Memories
You Am I - Heavy Heart
posted by teem at 11:41 PM on May 8, 2006

Moby - Everloving

Hope you feel better soon.
posted by Skyanth at 11:42 PM on May 8, 2006

Two from Sinatra - 'It was a very good year' and 'Summer wind'.
posted by tellurian at 11:48 PM on May 8, 2006

I just came inside after sprawling out on the grass in the backyard, staring up at the starts through the tree branches and listening to his mix I made tonight, all the while wondering why on earth I have such a penchant for heart crushing songs of dispair. Some of the lowlights?

Songs Ohia-Goodnight Lover
Eels-Rags to Rags
A Dolorean cover of an Elliott Smith song-Biggest Lie
Mike Doughty-Only Answer
Coco Rosie-Tekno Love Song
Okkervill River-For Real
Eef Barzelay (from Clem Snide)-We Are Flowers

There's a Bright Eyes song called "It's Cool, We Can Still Be Friends" that I used to think was funny. It's really not.

And the Mountain Goats will completely eat your soul if you let them, but it's okay, because it's so so good at the same time. As in "Game Shows Touch Our Lives":
And I handed you a drink of the lovely little thing
On which our survival depends
People say friends don't destroy one another
What do they know about friends?
posted by redsparkler at 12:15 AM on May 9, 2006

I was staring at the stars, by the way. And it's "this mix I made tonight", although heaven knows if there was a him to be a his of "his mix" I would still probably put these sort of things on it. I'm just that type of gal.
posted by redsparkler at 12:16 AM on May 9, 2006

Tracy Chapman - Smoke and Ashes. Man, this one just aches

Tracy Chapman - Baby Can I Hold You Tonight. Ditto.

Beth Orton - I Wish I Never Saw The Sunshine. Leaves you in a puddle. The cry that puts you to sleep.

Jewel - You Were Meant for Me. I know, I know, but sooo sad, the poor thing.

Bob Dylan - Most of the Time. Oh dear.

Jimmy Cliff - Many Rivers to Cross - In my tragic funeral fantasy, this is playing. Must be the organ.

Annie Lennox - Love Song for a Vampire. If you've got any left in you, this'll wring it out. Powerful instrumentation. A sledgehammer in a silk glove (once it kicks in).

This is a newer entry but- Röyksopp - What Else Is There (Jaques Lu Cont Radio Mix). Go out and drink too much and then come home and get drunkweepy about her 'cause she ain't comin' back. Just dance (stumble) it out. Properly sad 80's synth and anguished mood. Bonus! - generic cool foreign accent. Gotta do the remix to get the good synth, not the regular version.

Cheezy? Maybe, but Bob Seger - Against The Wind. Ever since I saw it in that part of Forrest Gump where he's running to put the empty Jenny sorrow behind him, and this song is playing as he runs alone down an empty road, it has been redeemed from the too-characteristically-80s-to-be-applicable-now bin. Really very good.

REM - New Orleans Instrumental No. 1. No words and yet so sad. How it can be gentle and heartwrenching at the same time must be why they call them "artists".

Figurine - IMpossible. Heartbreak in the computer era. And the coolest sample sounds, most notably of a speeding racecar. zmmmmmmm

Postal Service - Nothing Better - Classic call-and-response, he-said/she-said. Maybe the only sad song ever to mention charts and graphs.

Dido - Life for Rent. Recognizing that you're wasting your life. There it goes.

Smashing Pumpkins - Landslide. More fragile than the Fleetwood Mac version.

Tom Petty Wildflowers. Love her enough to know she's better off without you.

Tom Petty - Time To Move On. A particular phase of life is over, like it or not. Gather your stuff and move on. The bittersweet sadness of resignation.

Morrissey - Every Day Is Like Sunday. This one's almost comfortingly sad. A blanket.

Morrissey - We'll Let You Know. Ouch. As the life drains out of you...

Morrissey - Come Back to Camden. Just lovely, but portrays a sad pathetic desperation. "I'll be gooood, I'll be gooood, I'll be gooood, I'll be goooood..."

This Mortal Coil - Song to the Siren. I bet they play this on the river Styx. This is what they should have played at the end of Star Wars III when all the Jedi were getting mowed down by turncoat stormtroopers. Would have been richly tragic. So sad. Otherworldly.
posted by kookoobirdz at 12:23 AM on May 9, 2006

Just to second: almost anything Nick Drake. "Oh Poor Boy" comes to mind.

Also, Gillian Welch: "Tear My Stillhouse Down", "One More Dollar", "Orphan Girl"
posted by trip and a half at 12:36 AM on May 9, 2006

Hmmm my specialist subject!

The Loneliest Guy - David Bowie
Letter To Hermione - David Bowie
Go Or Go Ahead - Rufus Wainwright
Leave Me Alone - New Order
Love letter - Nick Cave
You Don't Know What Love Is - John Coltrane

And again for real stomach crushing misery I second the whole of Berlin by Lou Reed.

Once you've got through everybody's suggestions above might I suggest you listen to Aqua's - Cartoon Heroes as a very good antidote to the blues?

And look after yourself!
posted by merocet at 12:43 AM on May 9, 2006

Sarah Polley's cover of The Tragically Hip's "Courage", on the soundtrack to "The Sweet Hereafter".
posted by the duck by the oboe at 12:48 AM on May 9, 2006

Saddest song I've ever heard: "Family Affair" by Abra Moore.

I first heard it on a rerun of an episode of Third Watch (the one where Sasha loses the baby and Ty finds out and goes to see her?!?!?? [/end fan boyishness]). I wasn't even watching TV - just listening - and this song played and I just started bawling like a little girl with a scraped knee.

Now I have to listen to it and cry again.
posted by damnjezebel at 12:50 AM on May 9, 2006

"Memories of Green" by Vangelis - on the Blade Runner soundtrack.
posted by redteam at 12:51 AM on May 9, 2006

Magnetic Fields - My Only Friend
Beach Boys - I Guess I Just Wasn't Made For These Times
Caetano Veloso - Cucurrucucu Paloma (or Harry Belefonte, Celia Cruz, Joan Baez, or many, many more)
John Cale - Amsterdam
Curtis Mayfield - Now You're Gone
K. McCarty - Going Down, Desperate Man Blues (these are Daniel Johnston covers, and are a lot more polished than the originals.)
most of Jens Lekman's Oh You're So Silent Jens
Ted Daffan's Texans - Born to Lose
The Mekons - Please Don't Let Me Love You
Palace - New Partner
The Modern Lovers - Hospital
The Zombies - A Rose for Emily
Sonic Youth - Little Trouble Girl
Yo La Tengo - The Crying of Lot G
Astrud Gilberto - Felicidade (Happyness) (that is, regarding the fleeting nature of)
Elis Regina & Tom Jobim - Triste (Sad)
--You'll find lots of versions of the last two, including some in English.
posted by hydrophonic at 12:55 AM on May 9, 2006

You're Beautiful by James Blunt. I so can't figure out whether I love this song or hate it...
posted by misozaki at 1:00 AM on May 9, 2006

Matthew Good Band – Man of Action, Running for Home
posted by oaf at 1:03 AM on May 9, 2006

Led Zeppelin - Since I've Been Loving You
Radiohead - True Love Waits
Blend - Communicate
Blind Melon - Soul One
Pink Floyd - Comfortably Numb
Garbage - Cup of Coffee
posted by number9dream at 1:03 AM on May 9, 2006

i can't believe no one has ever said San Diego Serenade by Tom Waits. I think that is the absolute saddest song ever written like ever. That is melancholy transubstantiated into vinyl
posted by BigBrownBear at 1:13 AM on May 9, 2006

Also, On the Nickel by Tom Waits.
posted by sockpup at 1:27 AM on May 9, 2006

No Distance Left to Run - Blur
posted by jontyjago at 1:32 AM on May 9, 2006

"Young & Innocent Days" the Kinks
"Dido's Lament" Purcell
"Just the Motion" Richard/Linda Thompson
"The West Coast of Claire" Planxty
"Family Business" Kanye
"No Expectations" the Stones
"Mood Indigo" Duke Ellington
posted by minkll at 1:58 AM on May 9, 2006

Tiny Tears - Tindersticks
posted by crocomancer at 1:59 AM on May 9, 2006

I second "Family Business" Kanye West.
posted by jne1813 at 2:25 AM on May 9, 2006

Oh, and Elliot Smith - Miss Misery
posted by jne1813 at 2:26 AM on May 9, 2006

Depeche Mode - Blasphemous Rumours
posted by martinrebas at 2:47 AM on May 9, 2006

"Goodbye" and "Lonlier Than This" by Steve Earle.
posted by essexjan at 2:52 AM on May 9, 2006

Ditto Croce's "Photographs and Memories," which I just heard a couple of weeks ago for the first time in ages; I had never realized just how devastating it is. "Operator" is up there, too.

Warren Zevon's "Keep Me In Your Heart" chokes me up, too.

Now, if you want the whole bottoming out (not so much from sadness but overall depression)/developing a positive attitude experience, I recommend the Eels' "Electro-Shock Blues" album.
posted by kimota at 3:40 AM on May 9, 2006

Oh, and if you want to take your chances, there's always Gloomy Sunday.
posted by kimota at 3:42 AM on May 9, 2006

"The Saddest Song I've Got" by Annie Lennox is, well, damn sad.
posted by Dreama at 4:03 AM on May 9, 2006

For seriously wrenching heartache - "Mojo Pin" - Jeff Buckley
posted by Fejery at 4:50 AM on May 9, 2006

Ok among those I didn't find mentioned in previous threads, these are some of my own favourite sad songs, from obvious big melodramatic killers (like, er, the first ones!) to subtler pleasantly melancholic tunes, but not sad as in depressing, well at least not to me:

- Led Zeppelin - Babe I'm Gonna Leave You
- Elvis - Are You Lonesome Tonight
- Calexico - Missing
- Calexico - Bloodflow
- Beck - Nobody's Fault But My Own
- Beck - Already Dead
- Johnny Cash/Bob Dylan - Girl From The North Country
- Gram Parsons & Emmylou Harris - Love Hurts
- The Kinks - Waterloo Sunset
- Cast - Walkaway
- Depeche Mode - Home
- Babyshambles - New Love Grows On Trees
- I Am Kloot - From Your Favourite Sky
- I Am Kloot - The Same Deep Water
- Radiohead - Scatterbrain
- Andrew Bird's Bowl Of Fire - Fatal Flower Garden
posted by funambulist at 5:34 AM on May 9, 2006

And speaking of melodramatic, if you like the genre, there were a couple of killers on Almodovar's High Heels soundtrack, the two non-instrumental tracks sung by Luz Casal - "Un Ano De Amor" and "Piensa En Mi".
posted by funambulist at 5:41 AM on May 9, 2006

Violent Femmes - Johnny
Violent Femmes - Please don't go
posted by davey_darling at 5:50 AM on May 9, 2006

"Gone For Good" - Morphine
posted by Lucinda at 6:02 AM on May 9, 2006

i have to second (or is it third by this point) elliott smith's miss misery
i have seen several mountain goats suggestions but have not seen "cubs in five" mentioned yet.
archers of loaf - web in front
posted by phil at 6:03 AM on May 9, 2006

Camellia by the Buried Beds. It will gut you.
posted by theinsectsarewaiting at 6:11 AM on May 9, 2006

Dido - "White Flag"
posted by dagnyscott at 6:42 AM on May 9, 2006

If you like singer-songwriter types, David Wilcox (the American David Wilcox, that is) has lots of sad songs. A friend of mine used to come over and ask if we could listen to "that sad guy."

One of my favorites is "Language of the Heart"-
I won't keep on calling your number if you never have the time
I don't want to claim you or blame you, but you're always on my mind
You had no idea I would love you
It comes as a total surprise
And you shake your head slowly and smile
At the tears in my eyes

Dar William's version of The Band's "Whispering Pines" is just haunting.

Patty Larkin-"Angels Running"
Jonatha Brooke- "Inconsolable"
Jane Siberry- "The Walking and Constantly"
posted by Biblio at 6:44 AM on May 9, 2006

James Keelaghan - Cold Missouri Waters
also covered by Cry, Cry, Cry

Always gut wrenching for me, but that might just be because it's about 13 kids dying while fighting the Mann Gulch wild fire. If you read "Young Men and Fire" it might make it more poignant.
posted by Seamus at 6:59 AM on May 9, 2006

Most anything by the Smiths? In particular "Back to the Old House" and "Please Please Please Let Me Get What I Want"

Also, this question has been asked before I am quite sure.
posted by chunking express at 7:00 AM on May 9, 2006

Tough one. I generally choose folk singers for the saddest songs as they have an intimacy especially with an acoustic guitar - especially when coupled with a violin.

Cat Stevens: Sad Lisa (oops, piano)
Lucinda Williams: Sweet Old World
Don MacLean: Vincent
Gordon Lightfoot: Song for a Winters Night
Bruce Springsteen: The River
REM: Everybody hurts. (little cheesy but OK)

Lots of old classic cowboy songs 'bout hurtin'. It depends on your particular genre. I happen to LOVE Patsy Cline, but YMMV.
posted by fox_terrier_guy at 7:05 AM on May 9, 2006

Ditto on The Mountain Goats - No Children.

The Mountain Goats - Pale Green Things
Arcade Fire - In the Backseat
John Lennon - Nobody Loves You When You're Down and Out
Neutral Milk Hotel - Holland 1945
The Beatles - For No One
Elliott Smith - I Didn't Understand
Camera Obscura - Books Written for Girls
John Vanderslice - Dead Slate Pacific (and Golden Gate)
Neutral Milk Hotel - You've Passed
posted by ludwig_van at 7:17 AM on May 9, 2006

Patty Griffin - Rain, Top of the World, Goodbye, Mother of God, many others.
posted by nelleish at 7:54 AM on May 9, 2006

not sure how it slipped my mind in my first post but

willie nelson's permanently lonely

should make the list. the version off of the crazy sessions might be the saddest song ever
posted by phil at 7:54 AM on May 9, 2006

Ryan Adams -- Sweet Carolina. Or really the whole Heartbreaker album.
posted by M.C. Lo-Carb! at 7:55 AM on May 9, 2006

The Johnny Cash cover of I See a Darkness
Leonard Cohen - Night Comes On
Tom Waits - A Little Rain
Townes Van Zandt - $anyTownesVanZandtSong
posted by Hildago at 8:39 AM on May 9, 2006

Nine Inch Nails - Every Day is Exactly the Same
posted by GMD1987 at 8:40 AM on May 9, 2006

Henryk Mikołaj Górecki's Third Symphony, "subtitled Symphony of Sorrowful Songs (Symfonia pieśni żałosnych). Slow and contemplative, the three movements are composed for orchestra and soprano solo. The words of the first movement are from a 15th century lament; the words of the second were written by a teenage girl, Helena Błażusiak, on the wall of a Gestapo prison cell in Zakopane and invoke the protections of the Virgin Mary; the third movement is a folk song. The first movement, an extended canon for strings, takes up around half the playing time; it uses a battery of double basses to build slowly to an exquisite outcry from the soprano, before retreating to its foundation. Of the three movements, the second - lasting about eight minutes - is probably the most frequently listened to. [...] An acclaimed recording of the symphony -- performed by the London Sinfonietta conducted by David Zinman with the solo part sung by soprano Dawn Upshaw -- was released in 1993."
posted by xod at 8:49 AM on May 9, 2006

Beth Nielsen Chapman - "Sand and Water"
posted by needs more cowbell at 8:57 AM on May 9, 2006

The Smashing Pumpkins have a lot of sad songs, but Shame from the Adore album takes the cake imo.

Also, almost the entire Sea Change album by Beck.
posted by Devils Slide at 9:00 AM on May 9, 2006

what, nobodies mentioned "Love Hurts" by Nazareth yet?
posted by cosmicbandito at 9:05 AM on May 9, 2006

I never really thought of No Children as a particularly sad Mountain Goats song. I heard it as a childish expression of frustration by adults. It has an Edward Albee quality. It's so blunt and brutal that our reaction is to laugh. YMMV. It is one of my favorite Mountain Goats songs though. Tallahassee is certainly a very sad album taken as a whole.
posted by Hildago at 9:35 AM on May 9, 2006

Soundtrack from The Saddest Music in the World?
posted by xod at 9:40 AM on May 9, 2006

Second Górecki's Symphony of Sorrowful Songs.

I also have a place in my heart for Samuel Barber's Adagio for Strings arranged for vocals (Agnus Dei). The version I am thinking of is on a CD titled "Barber's Adagio," which contains like 8 different arrangements of the song and might be available through Amazon. The Agnus Dei wasn't available through ITMS the last time I looked.
posted by jeversol at 9:50 AM on May 9, 2006

Pretty good. I think things, and xod types them. Both suggestions. Especially the 1993 Goreki.
posted by Ohdemah at 9:54 AM on May 9, 2006

These are the songs I can't listen to on the subway because I'll start bawling like an idiot:

The Pretenders - "I'll Stand by You"
Leonard Cohen - "Hallelujah" (this one gets me going right away)
Seether - "Broken"
Bonnie Raitt - "I Can't Make You Love Me"
posted by Evangeline at 9:58 AM on May 9, 2006

Anuna-- Siuil a Ruin, and a lot of other traditional Irish tunes, are very sad. But Siuil a Ruin is my favorite, and Anuna's is my favorite version of it.

Billie Holiday always sounds sad to me, more so in tone than in lyrics.

Garbage have a number of songs that are quite sad-- "You Look So Fine", "Happy Home", "So Like a Rose" and "Milk" among them.

Fiona Apple, "Pale September".

Howard Shore and Emiliana Torrini, "Gollum's Song".

Annie Lennox, "Into the West". (Actually, I find all of the LOTR soundtracks deeply affecting, but not always in a sad way.)

Kate Bush- "King of the Mountain", "How to Be Invisible", "Top of the City", "Army Dreamers" (*especially* "Army Dreamers"), "Breathing", "The Man With the Child in His Eyes" (especially that one, too), "The Empty Bullring", "Lord of the Reedy River", "Under the Ivy", and the entirety of her albums Lionheart and Hounds of Love.

Pretty much everything Leonard Cohen has ever done has a melancholy edge; the man can't sing, of course, but his lyrics are incredible.

Loreena McKennitt, "Skellig".

"Snow", "Zero Hour" and "Solitude by the Window" are all very sad, if you can find them. They're from the Noir anime OST.

Likewise, much of The Seatbelts' work from the Cowboy Bebop OSTs is very bluesy and melancholy, particularly "Blue", "Rain", "Dijurido", "Forever Broke", "No Money", "See You Space Cowboy" and "Real Folk Blues" (look up a translation of the lyrics.)

Tori Amos, "Little Earthquakes", "Winter", "Playboy Mommy", "Me and a Gun", and "Muhammed My Friend".

The saddest songs ever? A tossup between the Seatbelts' "Good Night, Julia", and Kate Bush's "My Lagan Love".
posted by WidgetAlley at 10:01 AM on May 9, 2006

The Cat Carol. Cheesy? Quite possibly. Sad? Oh dear lord, yes. Sample here.
posted by GuyZero at 10:19 AM on May 9, 2006

what, nobodies mentioned "Love Hurts" by Nazareth yet?

er, I always thought it was a Gram Parsons song cos that's the first I ever heard! and I'd never heard of Nazareth (I wasn't around yet at that time) so I went looking on AMG and found out the original is by The Everly Brothers, and both versions are covers. I had no idea. (I love finding out this kind of stuff)
posted by funambulist at 10:33 AM on May 9, 2006

(...not that I have any clue who exactly the Everly Brothers are either, but I do like finding out this stuff about different covers of songs I like and bands that were around before I was! so thanks for bringing that up, cosmicbandito!)
posted by funambulist at 10:37 AM on May 9, 2006

Erm, to make up for derail, just occurred to me no one yet mentioned Morrissey's and other covers of Moon River from tellurian's recent MeFi post.
posted by funambulist at 10:41 AM on May 9, 2006

Wow, nobody's mentioned Pearl Jam's "Black" yet? Maybe I'm the only one who finds it so sad.

Other sad songs:

Tool's Wings for Marie (part 1 and 2) off of the new album (though you need some background to understand the sadness -- his mother, Marie, was paralyzed by a stroke for 27 years, which is roughly 10,000 days hence the album title, before she passed away).

Michael Andrews - "Mad World" (can be found on the Donnie Darko soundtrack)

Nine Inch Nails - Something I Can Never Have (this was surely much more effective when I was like.. 14 or whatever, but I remember it being really sad back then)

Lifehouse - Simon (a tremendously sad song about a kid who is bullied)

Incubus - I Miss You (maybe more sentimental than sad, but sad to me nonetheless)

Dashboard Confessional - Screaming Infidelities
Dashboard Confessional - Best Deceptions
Dashboard Confessional - Again I Go Unnoticed

[yes, despite my age I'm apparently a sucker for really straightforward juvenile lyrics with no subtlety whatsoever]

I could list lots of others, but I should GBTW ...
posted by twiggy at 11:26 AM on May 9, 2006

Belle and Sebastian - Fox in the Snow

It's so sad, I can hardly stand to listen to it. Here is the photo to go along with it. Poor little fox.

Also:
Ben Harper - Another Lonely Day.
posted by 912 Greens at 1:07 PM on May 9, 2006

VNV Nation - Holding On.
posted by bitmage at 1:10 PM on May 9, 2006

Listening to music in a major key after Auschwitz is barbaric [/Adorno riff].
posted by xod at 3:34 PM on May 9, 2006

I should've mentioned John Lennon's "Mother."
posted by kimota at 4:11 PM on May 9, 2006

Alphaville - Forever Young. Always makes me cry.
posted by candyland at 6:02 PM on May 9, 2006

OK, so I'm a bit late to this thread, and I don't have access to most of my CD collection right now (it's packed up and somewhere between California and England), but here's some artists who have plenty of sad songs to choose from:
Low
Rex
Tindersticks
Arab Strap
Mike Johnson
Damien Jurado
Iron & Wine
Lambchop
Michael Gira/Swans/Angels of Light
Joy Division (though they were often more depressing than sad)
Leonard Cohen
Damon & Naomi (they even have an album called More Sad Hits)
Mazzy Star
Portishead
Thalia Zedek
Varnaline
posted by klausness at 1:22 AM on May 12, 2006

WidgetAlley mentioned Billie Holiday upthread and I recalled "Strange Fruit".

Southern trees bear strange fruit,
Blood on the leaves and blood at the root,
Black bodies swinging in the southern breeze,
Strange fruit hanging from the poplar trees.

Pastoral scene of the gallant south,
The bulging eyes and the twisted mouth,
Scent of magnolias, sweet and fresh,
Then the sudden smell of burning flesh.

Here is fruit for the crows to pluck,
For the rain to gather, for the wind to suck,
For the sun to rot, for the trees to drop,
Here is a strange and bitter crop.

Centuries of sadness in song.
posted by sockpup at 6:40 PM on May 13, 2006

Also, Lori Mckenna - "What's One More Time?"
posted by sockpup at 7:33 PM on May 13, 2006

Neil Young - "Birds"

If I should fly away without you
Shadow on the things you know
Feathers fall around you
And show you the way to go
It's over
posted by sockpup at 8:58 PM on May 13, 2006