What are the saddest songs?

September 21, 2005 10:09 PM

What are the saddest songs you can think of?

In particular, I'm thinking of cathartically sad songs.

posted by Sticherbeast to media & arts (155 comments total)

Indigo Girls, "In Love With Your Ghost" and "Love Will Come To You"

Phew.
posted by ZakDaddy at 10:11 PM on September 21, 2005

Forever Young by Alphaville - the slow version is just about the saddest song I ever heard. I guy I knew tangentially died when I was in college and I didn't really feel anything until I heard that song on the radio. I just broke down and wept.
posted by any major dude at 10:11 PM on September 21, 2005

Glah, I suck. "In Love With Your Ghost" is, of course, simply "Ghost." And both tracks are off of Rites of Passage.
posted by ZakDaddy at 10:13 PM on September 21, 2005

Tears in Heaven by Eric Clapton.

Perhaps not sad, exactly, but Trouble by Cat Stevens.

Everybody Hurts, REM
posted by ashbury at 10:14 PM on September 21, 2005

"Brand New Love" by Sebadoh.

"Love Will Tear Us Apart" by Joy Division is a close second.
posted by 23skidoo at 10:18 PM on September 21, 2005

"Without You" by Harry Nilsson.
posted by I Foody at 10:21 PM on September 21, 2005

Elliott Smith, "Twilight"
posted by speicus at 10:24 PM on September 21, 2005

Alexi Murdoch's "Song For You"
Jewel's "Amen"
Poe's "Fly Away"
Leonard Cohen's "Hallelujah"
posted by sarahnade at 10:25 PM on September 21, 2005

Selmasongs, the Dancer in the Dark Soundtrack.
posted by Kwantsar at 10:27 PM on September 21, 2005

Johnny Cash - "Hurt"
Radiohead - "I Will"
Death Cab for Cutie - "Transatlanticism"
Steve - "I Am Here"
posted by kyleg at 10:34 PM on September 21, 2005

I might have the title wrong, but "Cat's in the Cradle".
posted by acoutu at 10:35 PM on September 21, 2005

Symphony of sorrowful songs, Gorecki.
Second on the Johnny Cash.
posted by philfromhavelock at 10:41 PM on September 21, 2005

Songs: Ohia - How to Be Perfect Men
Skip James - Devil Got My Woman
RJD2 - Hidden Track on Deadringer
Erik Satie - Gymnopedie
Nina Simone - Plain Gold Ring
Beach Boys - God Only Knows
The Smiths - Please, Please, Please Let Me Get What I Want
Otis Redding - I've Been Loving You Too Long
Gram Parsons - $1000 Wedding
The Out Circuit - Phantom City Skyline
Bola - Aguilla
Richard Crandell - Abstraction #1
Sunny Day Real Estate - How it Feels to Be Something On
Stars of the Lid - Requiem for Dying Mothers Pt. 1 and 2
Pavement - Here
Elliot Smith - Needle in the Hay
Far - Girl
Zelda 64 - Windmill Theme
Xela - Japanese Whispers
Mahmoud Ahmed - Bemen Sebeb Letlash
Al Green - Have You Been Making Out OK?
Jefferson Airplane - Today
Shigeru Umebayashi - Yumeji's Theme
posted by cloeburner at 10:44 PM on September 21, 2005

Puccini, Tosca -- E Lucevan le Stelle.
posted by sbutler at 10:45 PM on September 21, 2005

Billy Bragg's "Tank Park Salute"
Lynyrd Skynyrd's "Tuesday's Gone" (which has very sad lyrics and saddest guitar and drums parts ever, making it a contender for saddest song ever, but the piano part is downright chirpy)
posted by kirkaracha at 10:47 PM on September 21, 2005

Show of Hands - The Preacher

Don't know why, but its just... powerful for some reason.
posted by devilsbrigade at 10:47 PM on September 21, 2005

Bonnie Prince Billy - I See a Darkness
posted by flod at 10:47 PM on September 21, 2005 [1 favorite]

"A Cottage for Sale" (especially as sung by Judy Garland on her variety show)

"I Get Along Without You (Very Well)"

"Not a Day Goes By" (from Merrily We Roll Along)

"Nickel Ride" by Peggy Lee (a rare track available on a special Rhino Records CD release of Peggy's masterful Lieber & Stoller record, Mirrors -- and a must for any fan of "Is That All There Is?")

"Conversations with a Ghost" by Ellis Paul and Patty Griffin

"Children & Art" as sung by Holly Cole

"Sally's Pigeons" by Cyndi Lauper

"One for My Baby (And One for the Road)" Watching Bette Midler sing it to Johnny Carson still breaks me up
posted by mrkinla at 10:53 PM on September 21, 2005

Hmmm... I was on a sad song jag for quite a while, but I'll try to keep it to just the saddest few...

Led Zeppelin - Since I've Been Loving You
Radiohead - True Love Waits
Blend - Communicate
Garbage - Cup of Coffee
posted by number9dream at 10:54 PM on September 21, 2005

xiu xiu's cover of fast car
sparkle horse - its a wonderful life
posted by atom128 at 10:58 PM on September 21, 2005

I've Seen It all - Björk & Thom Yorke
Here Today - Beach Boys
Wishful Thinking - Wilco
Brick - Ben Folds Five
Vocalise - Rachmaninoff
posted by I Love Tacos at 10:58 PM on September 21, 2005

R.E.M. - E-bow the Letter
Rebekah del Rio - Llorando (Crying), from the Mulholland Dr. soundtrack
The Flaming Lips - Waitin' for a Superman
posted by flod at 11:02 PM on September 21, 2005

The Beautiful South - "Sail This Ship Alone"
posted by pompomtom at 11:07 PM on September 21, 2005

Choral Music probably isn't going to get many entries here, so I thought I'd suggest two:

(1) When David Heard by Eric Whitacre. This is based off a biblical passage where David laments the death of his son, Absalom. I have no idea what it's like to lose a child, but I think Whitacre succeeded at pouring that grief into the music.

" I am not generally an emotional person. I have never cried at a movie, I could probably count the times I've cried since I was 8 on my fingers...I heard When David Heard and I was taken away. I felt like I was in a dreamworld. The intense sorrow in the piece is staggering. I broke down and cried like a baby."

(2) Who is Crying by Mack Wilberg. I believe it's an arrangement of an Eastern European folk tune, with lyrics like "Who is crying, what lamenting, sounds so sadly throught the night? They are orphan children crying, bowed beneath their master's might..."
posted by weston at 11:08 PM on September 21, 2005

Cigarette - Ben Folds Five
Bulletproof... I Wish I Was - Radiohead
My Sundown - Jimmy Eat World
One of These Things First - Nick Drake
posted by I Love Tacos at 11:16 PM on September 21, 2005

The twelve-minute version of "Walk On By" by Isaac Hayes.
"I'm So Lonesome I Could Cry"...Johnny Cash/Nick Cave or Al Green or Hank Williams, depending upon your mood.
"People Ain't No Good", also by Nick Cave
"Nobody Knows You When You're Down And Out", Bessie Smith
"I Wish It Would Rain", The Temptations
"Jesus' Blood Never Failed Me Yet", Gavin Bryars

and because I am a huge cheeseball..."Bright Eyes" by Art Garfunkel. I realize this blows any theoretical cred I might have.
posted by Vervain at 11:18 PM on September 21, 2005

Well, this is my second time in the past 24 hours I've mentioned it on AskMe, but... Twelve O'Clock Whistle by James McMurtry. Other contenders are "Joey" by Concrete Blonde, "Runaway Train" by Soul Asylum, and "Raining in Baltimore" by the Counting Crows (though that entire album - August and Everything After is, according to Adam Duritz himself, "mopey"). Same band but different album (Recovering the satellites); "Miller's Angels." Pretty much everything I've heard by Mark Eitzel has made me want to slit my wrists. "This Perfect World" by Freedy Johnston has the line "And these pills won't even let me cry;" that always gets me. Someone's already mentioned a couple songs off of Rites of Passage but I gotta say that, for me, the saddest song on that album and probably the saddest song the Indigo Girls have ever recorded is their cover of the Dire Straits' "Romeo and Juliet." The DS version does nothing for me, I hear the IG version once and I can't get out of bed for days. Also worth mentioning; The Smithereens' "Blood and Roses."

I'm sure I'm forgetting lots of brutally depressing stuff but this ought to do for now.
posted by Clay201 at 11:18 PM on September 21, 2005

The Taxi Ride - Jane Siberry
Apology for An Accident - American Music Club
Soul In Isolation - Chameleons
He Needs Me - Nina Simone
A House Is Not A Home - Brook Benton
Godamn the Sun - Swans
Alone Again, Naturally - Gilbert O'Sullivan
Too Pure - Sebadoh
The Confidential Agent - American Music Club
Still Too Soon To Know - Elvis Costello & the Attractions
Black Heart - Calexico
posted by black8 at 11:20 PM on September 21, 2005 [1 favorite]

"Silentium", Arvo Pärt—most depressing song-length musical piece ever.

"Into Dust", Mazzy Star.

"Teardrop", Massive Attack.

"Gnossienne #3", Erik Satie

"Slit my Wrists", The Loud Family. Not for amateur saddoes, you might be able to find "Inverness" which is also highly sad in a less over the top way, and there's some Aimee Mann live version of it out there or something.

"All her Favorite Fruit", Camper van Beethoven, perhaps more bittersweet than sad.

23skiddo: hey I know those songs well! For depressing Joy Division, I like "Atmosphere"

"Jizzlobber", Faith No More, if your sadness has a strong element of fucked up self-loathing (and maybe general loathing). A really strong element. Painful but with a great cathartic ending. Along the same vein of rockin' depressed catharsis, the Cranes' "Sixth of May" and Slint's "The Captain".

"Catch the Breeze", Slowdive, why not.

"Wandering Star", Portishead, is more depressing than their "Sour Times" in my opinion but Sour Times tends to attract more of the habitually sad.

As a wee emo I seem to remember Toad the Wet Sprocket's Pale as a sadfest, "I Think About" especially, but then I was of a depressionable age dimly remembered.

Of course something like "Eleanor Rigby" by the Beatles. "Nowhere Man" I guess, etc.

"Last Year", Go Sailor.

"Black Diamond Bay", Bob Dylan

"In Dark Trees", Brian Eno, short instrumental bit, more spooky than sad. Most of the "Another Green World" album is good stuff.

"Tail Lights Fade", Buffalo Tom, sorta.

"Pictures of You", the Cure

Top it all off with "We're Both Confused" by Luna(^2) and you'll be whole again.
posted by fleacircus at 11:23 PM on September 21, 2005

"Last Kiss", J Frank Wilson & The Cavaliers or Pearl Jam
posted by phox at 11:31 PM on September 21, 2005

Autechre - Yulquen
posted by cloeburner at 11:33 PM on September 21, 2005

Adagio for Strings, Op. 11 by Barber. Most people probably know it as "the 'Platoon' song." My wife and I refer to it as "music to commit suicide by."

I also find Ave Maria to be a real downer. Sarah Brightman's version in particular is just the right song to accompany a cold, rainy day. I know that, translated, it isn't too much of a downer, but my Latin isn't good enough to hum along in the translation, so it still gets me.
posted by robhuddles at 11:52 PM on September 21, 2005

Red House Painters - Katy Song
Red House Painters - Revelation Big Sur
Mark Kozelek - Admiral Fell Promises
The Cure - Untitled (Live version on Entreat)
Prefab Sprout - When Love Breaks Down
Autechre - Draun Quarter
Lackluster - The Weakened State
This Mortal Coil - A Single Wish
posted by shortfuse at 11:52 PM on September 21, 2005

Wow, so many good songs there, are we all a bunch of sad-sacks.

My personal suggestion is:

Lonlier Than This - Steve Earle

I never get more than a few bars into the song before tearing up.
posted by Cosine at 11:52 PM on September 21, 2005

Trinity Sessions album by the Cowboy Junkies.
posted by small_ruminant at 12:02 AM on September 22, 2005

I'm assuming sad songs are different than depressing songs. Depressing songs are easier to find.
posted by small_ruminant at 12:05 AM on September 22, 2005

They're doubtless not the saddest, but I used to find Lucky by Radiohead and some of the Manic Street Preachers’s songs, Roses in the Hospital for example, did the cathartic thing for me, as did Sweet Honey in the Rock’s version of Wade in the Water…
posted by misteraitch at 12:09 AM on September 22, 2005

Second kyleg's recommendation: "Transatlanticism," by Death Cab for Cutie.

I suppose it's all invididual, though, what speaks to you, personal circumstances & whatnot. This one gets to me.

Actually that album's full of them. "Tiny Vessels" always makes me sad simply because it's so bleak. Nasty little ditty.
posted by donpedro at 12:10 AM on September 22, 2005

Devin The Dude "Anythang"
Curtis Mayfield "Here But I'm Gone"
Ruby Johnson "I'll Run Your Hurt Away"
Low "Last Night I Dreamt That Somebody Loved Me" (the Smiths original is pretty sad too, of course)
Dusty Springfield "No Easy Way Down" (and several other songs from "Dusty in Memphis"
Dntel "Why I'm So Unhappy"
The Streets "Dry Your Eyes"
The Rolling Stones "I Got The Blues"
Johnny Hartman & John Coltrane "Lush Life"
Rjd2 "Making Days Longer"
Teddy Bears "To Know Him Is To Love Him" (the absolute worst song to listen to when you're missing someone)
Frank Sinatra "Can't We Be Friends"
Neil Young "Old Man"
Blanche "Who's To Say"
The dB's "Moving In Your Sleep"
Magnetic Fields "Come Back From San Francisco"
Charlie Rich "Life's Little Ups And Downs"
posted by TayBridge at 12:13 AM on September 22, 2005

Also: "The Distance Between You and Me," by Dwight Yoakam.

On preview, TayBridge: I always picture "Come Back From San Francisco" as having a happy ending. Funny, different reactions.
posted by donpedro at 12:18 AM on September 22, 2005

plastic ono band - 'god'
posted by Satapher at 12:20 AM on September 22, 2005

by john lennon ;)
posted by Satapher at 12:21 AM on September 22, 2005

"Evie's Tears" and "Western Sky", both from Freedy Johnston
"In The Wee Small Hours of the Morning" - Frank Sinatra
"Your Dictionary" - XTC
"Trafalger Square" - Chris Difford

Every one of the above gets me choked up.
posted by gfrobe at 12:22 AM on September 22, 2005

One of These Things First - Nick Drake

I admit I'm bad at lyrics, but musically I always found this one of his happier pieces. I'd go with "Day is Done" from him.

Some other suggestions..

Fiona Apple - Sullen Girl
Elliott Smith - almost his whole back catalog
Smashing Pumpkins - Galapagos or Blank Page
ABBA - The Winner Takes It All (ultimate breakup song?)

I can't really back these suggestions of things like Death Cab for Cutie.. they're way too upbeat and cheery. Again, it's the music that does it for me, not the lyrics, so I might be missing something. Supposedly The Cardigans have really depressing lyrics behind their pop facade, too.
posted by wackybrit at 12:23 AM on September 22, 2005

It's totally 80's but
Nothing Compares 2 U - Sinead O'Connor

Brings me right back to high school everytime.
posted by madajb at 12:30 AM on September 22, 2005

Top o' the head:

'Holding Back The Years', Simply Red (no, really)
'Revelator', Gillian Welch
'I Want You', Elvis Costello (yes for cathartic)
'If You Have To Ask', Mark Eitzel (one among many)
'Ne Me Quitte Pas', Jacques Brel
'Don't Make Me Over', the Petula Clark version
'So Far Away', Carole King
'Low', R.E.M.
'History', The Verve

Lots by Richard Thompson, especially on Shoot Out The Lights, but also 'When The Spell Is Broken' from Across A Crowded Room.
posted by holgate at 12:31 AM on September 22, 2005

Here's some by a few of my favorite bands, YMMV, of course, but these songs have always struck a chord with me, in a sad sort of way:

Radiohead:
-Exit Music (For a Film)
-Fake Plastic Trees
-Let Down
-No Surprises
-Bullet Proof...I Wish I was Dead.

Barenaked Ladies:
-War on Drugs
-Brian Wilson
-What a Good Boy
They're more popular for their sillier songs, but these songs just manage to wrench my gut. They're a weirdly bipolar band

Travis:
-Paperclips
-Falling Down
-Funny Thing
-The Humpty Dumpty Love Song

Christ, we're a bunch of sad sacks, aren't we? Someone needs to start a happy cheerful love songs thread after this one's over.
posted by kosher_jenny at 12:31 AM on September 22, 2005

Symphony of sorrowful songs, Gorecki.

I'll second that. I tend to listen to it when I'm really down precisely for the cathartic effect the original poster was talking about. It's simple but incredibly powerful.

"Silentium", Arvo Pärt—most depressing song-length musical piece ever.

Haven't heard that one, but Pärt's Cantus in Memory of Benjamin Britten (on the Tabula Rasa CD) certainly fits the bill as well.

Adagio for Strings, Op. 11 by Barber.

I can second that one as well. There's a reason it has a dense history of being performed in times of mourning.

Shostakovich's string quartets can be pretty wrenching, especially the last ones and especially #15.

A few months ago I heard the end of Puccini's La Bohème on the radio for the first time. Great music frequently gives me chills, but from some combination of that particular day, the music, the performance, the time and place... it's the only time music has ever moved me to tears.
posted by musicinmybrain at 12:37 AM on September 22, 2005

"Silentium", Arvo Pärt—most depressing song-length musical piece ever.

Oh, if we're going into classical music, then 'Cantus In Memory of Benjamin Britten'. Not depressing, just heartbreaking. And much of Pärt fits the 'cathartic' mode.
posted by holgate at 12:39 AM on September 22, 2005

Sacrifice - Lisa Gerrard/Pieter Bourke (from the soundtrack of The Insider)
posted by Skyanth at 12:57 AM on September 22, 2005

Shannon – Henry Gross
Fairytale of New York – The Pogues
Brother, Can You Spare a Dime? – Bing Crosby
posted by timeistight at 1:09 AM on September 22, 2005

Lambchop - Catapillar
Jesse Sykes - You Are Not Gotten Here
The Cure - Faith
Jim White - Christmas Day
Low - That's How You Sing Amazing Grace
Beck - Guess I'm Doing Fine
The Handsome Family - Last Night I Went Out Walking
Pedro The Lion - The Poison
posted by cali at 1:13 AM on September 22, 2005

Tom Waits, More than Rain.


Lyrics here
posted by Meatbomb at 1:26 AM on September 22, 2005

I'm late to the party, but I had to add my all-time favourite for lonely late nights:

One World by John Martyn (from the album One World)

The lyrics are simple and beautiful and the music haunting.
posted by chrismear at 1:30 AM on September 22, 2005

Curtis Mayfield - We People Who Are Darker Than Blue
Nitty Gritty Dirt Band - Mr Bojangles (just for the bit where his dog dies... **sniff**)
Isaac Hayes' 12 minute version of By The Time I Get To Phoenix (yo Vervain!)
posted by bifter at 2:14 AM on September 22, 2005

Cat Power - Colors And The Kids
Heavens To Betsy - Complicated
Cadallaca - Winter Storm '98
Delta Dart - Story Of My Life
Dilute - Sold
Gillian Welch - I Made A Lover's Prayer

To be honest, most of Cat Power's music is extremely sad.
posted by pollystark at 2:17 AM on September 22, 2005

Last Goodbye by Jeff Buckley, maybe anything from his Grace album...love his music.
posted by Chimp at 2:35 AM on September 22, 2005

"Alone again, naturally" - Gilbert O'sullivan. Though sometimes too cheesy to be sad..
posted by lemonpillows at 2:35 AM on September 22, 2005

Lots of Low tracks (but not from the last 2 albums) and "Stargazer" by The Zephyrs.
posted by NinjaPirate at 2:38 AM on September 22, 2005

Beach Boys - God Only Knows (played at a friend's funeral almost a year ago. On a miserable rainy day the song transformed the bleak municipal crematorium and there wasn't a dry eye in the house)

Jeff Buckley/Leonard Cohen/Kathryn Williams - Hallelujah
posted by patricio at 2:41 AM on September 22, 2005

Not a lot I can add here, but here's a couple.

You Never Know by Immortal Technique is very poignant.

Changes hits me kinda hard every time I hear it, mostly because the material is so old, and it sounds like it could've been written yesterday.

Civil War, too.
posted by Yelling At Nothing at 3:29 AM on September 22, 2005

"Is That All There Is?" - Peggy Lee
"While My Guitar Gently Weeps" - George Harrison
"Am I The Only One?" - Marc Anthony
"Una furtiva lagrima" - L'Elisir d'Amore, Donizetti (preferably sung by Pavarotti)
"Soave sia il vento" - trio from Cosí fan tutte, Mozart
posted by rob511 at 3:32 AM on September 22, 2005

eh, late to the party again, and TayBridge has already beaten me to Low's cover of 'Last Night I Dreamt...'

I'll throw in Sebadoh's 'Too Pure' which works as far as self-pitying sadness...
posted by anagrama at 3:32 AM on September 22, 2005

Easy's Getting Harder Every Day - Iris Dement
Hain't It Funny - k.d. lang
posted by phhht at 4:02 AM on September 22, 2005

"The saddest song" - Morphine
posted by springload at 4:03 AM on September 22, 2005

My brother recommends:

* Arvo Part - Festina Lente and Lamentate
* Theme from Twin Peaks (Fire Walk With Me) - Angelo Badalamenti
* Communication - The Cardigans
* Flair - Josh Rouse
* Theme from Schindler's List - John Williams
* My Curse - Afghan Whigs
* I Will Be There When You Die - My Morning Jacket
* Blackbird on the Wire - The Beautiful South
* Screen - Brad
* Curbside - Damien Jurado
* Timewatching - The Divine Comedy
*I See A Darkness - Bonnie 'Prince' Billy
posted by TheDonF at 4:06 AM on September 22, 2005

"This Woman's Work" by Kate Bush is guaranteed to make you cry.
posted by MsVader at 4:14 AM on September 22, 2005

Billy Bragg and Wilco- One By One
Palace- There Is No One What Will Take Care Of You
Kristen Hersh- Your Ghost

Second the Cat Power- almost everything by Cat Power is super depressing. I must be weird, because I find all the Sebadoh songs mentioned kind of uplifting and happy.
posted by banjo_and_the_pork at 4:20 AM on September 22, 2005

Greensleeves. (seriously)
posted by klarck at 4:41 AM on September 22, 2005

"Smoke" by ben Folds Five ... someone already listed "Cigarette" which is from the same album "whatever and ever amen."
posted by Makebusy7 at 4:53 AM on September 22, 2005

"Tiny Tears" - The Tindersticks.

And pretty much any Leonard Cohen song. I happen to think that "Hallelujah" is one of his more uplifting ones.
posted by blag at 4:55 AM on September 22, 2005

Gary Jules' remake of the Tears for Fears song Mad World on the Donnie Darko soundtrack is mighty sad.
Lyrics here.
posted by JuliaKM at 4:57 AM on September 22, 2005

How about an entire album: Blood on the Tracks by Bob Dylan.

Best breakup album ever
posted by poppo at 5:07 AM on September 22, 2005

Many by Merle Haggard. Two in particular: Footlights and Kern River.

Many by the Cowboy Junkies. These are the albums that you play while writing your suicide note.
posted by megatherium at 5:13 AM on September 22, 2005

He Stopped Loving Her Today by George Jones.
posted by uncleozzy at 5:16 AM on September 22, 2005

Sheila Behman's version of "Desperado" on the Langley Schools Music Project CD.
posted by MegoSteve at 5:24 AM on September 22, 2005

This has been asked before.
posted by amarynth at 5:27 AM on September 22, 2005

Joni Mitchell - Both sides now (new version)
Vince Gill - Hey God (written for golfer Payne Stewarts funeral)
Josh Groban - To where you are
Jane Siberry - Calling all angels
posted by adamfunman at 5:33 AM on September 22, 2005

And the start of autumn is just such a good time to ask this question.

"Lover, You Should Have Come Over", by Jeff Buckley.
"Little Triggers", by Elvis Costello
"I've Been Let Down," by Mazzy Star
"I Want You To Know" by Masha Qrella
"Helpless" by Neil Young
"Fruit Tree", by Nick Drake. Was going to say "Black Dog", but that's not sad, just unremittingly grim.
"Someone Who Cares", by The Only Ones.
"Plain Sailing," by Tracey Thorne
"Ella", by M.Ward
"This Is The Day," by TheThe.
"Eephus Pitch" by Willard Grant Conspiracy
"So Tired Of Being Alone", by Al Green
Any of the Arvo Part stuff mentioned so far, but I find Spiegel im Spiegel very melancholy. Beautiful, but achingly sad.
"Faith" by the Cure.
"Alone Again Or," by Love.

Think I might go and listen to some ska now to cheer myself up.
posted by reynir at 5:57 AM on September 22, 2005

"Eligy for Amy" by the Pat McGee Band
posted by NotMyselfRightNow at 6:00 AM on September 22, 2005

Pretend it's summer - Freedy Johnston
posted by any major dude at 6:13 AM on September 22, 2005

Niamh Parsons - "Clohinne Winds"
Moby - "My Weakness"
posted by fuzzbean at 6:28 AM on September 22, 2005

I'm way too late in here but, reading above, I can't believe no one mentioned Elvis Costello. There's inevitably an extremely sad song on pretty much all of his records. Jumping to mind:
Alison (of course) - My Aim is True
I Want You - Blood and Chocolate
After the Fall - Mighty Like a Rose
posted by leecifer at 6:33 AM on September 22, 2005

When I Was a Boy - Dar Williams
posted by amber_dale at 6:34 AM on September 22, 2005

A few I haven't seen here yet are:

"Pyramid Song" by Radiohead
"Bankrupt on Selling" by Modest Mouse
"A Man Needs a Maid" by Neil Young
"Strange Fruit" by Billie Holiday
"Oh Comely" by Neutral Milk Hotel is brutally sad.

Most of Chopin's Nocturnes are pretty sad, I find.
posted by saladin at 6:44 AM on September 22, 2005

Lighthouse Tale - Nickel Creek (?)
Vertebrae - Christine Fellows
posted by odinsdream at 6:44 AM on September 22, 2005

"Green and Grey" - New Model Army

... Like a lot of responders, I know a lot of sad songs, but not a lot of cathartic ones, unless reliving the grief that they bring is what you have in mind... in which case, I'm all over that.
posted by ChrisR at 6:47 AM on September 22, 2005

"You Were Always On My Mind" and "Blue Eyes Crying in the Rain" by Willie Nelson;
"One Step Up" by Bruce Springsteen;
"Blame It On My Youth" and the instrumental yet absolutely heartbreaking "Cinny's Waltz" by Holly Cole;

"Wrap Your Arms Around Me," by the Barenaked Ladies. Also I second their "What a Good Boy" - it was mentioned above;

"House of Dreams" by Blue Rodeo;

"Beautiful Goodbye", by Amanda Marshall.
posted by orange swan at 6:49 AM on September 22, 2005

"10:15 Saturday Night"-The Cure
posted by brujita at 6:52 AM on September 22, 2005

Thirty Years of Farming - Fred Eaglesmith - "thirty years of farming, thirty years of heartache, thirty years of day to day / Oh, my daddy stopped talking, the day the farm was auctioned / There was nothing left to say"

Hallelujah - Leonard Cohen or Jeff Buckley or Rufus Wainwright

Bells On - Sloan "If I had a funeral / would you even care?"

Anchorage - Michelle Shocked. Not *precisely* sad, but it definitely features a profound sense of "what if".

Long Black Veil - The Band (and others). An affair, murder, false conviction, lifelong mourning. What more could you want?

Heart Like a Wheel - Kate and Anna McGarrigle (and Billy Bragg did it very well too).

Take me down to the Infirmary - Cracker. A sad song from the least likely source. Awesome guitar too.

Jolie Louise - Daniel Lanois. Man gets married, man gets fired, man drinks a lot, man batters wife, loses wife, loses kids.

Long Gone Lonesome Blues - Hank Williams. "I'm going to find me a river / one that's cold as ice / and when I find me that river / Lord I'm going to pay the price / I'm going down in it three times / but lord I'm only coming up twice." Awesome yodeling too.

Down in the Tube Station at Midnight - The Jam. East Indian (?) man gets beaten (and killed?) by racists in a tube station while his wife waits at home for the takeaway curry.
posted by mikel at 6:54 AM on September 22, 2005

End of the Rainbow - Richard Thompson

"I feel for you, you little horror
Safe at your mother’s breast
No lucky break for you around the corner
‘Cos your father is a bully
And he thinks that you’re a pest
And your sister, she’s no better than a whore

Life seems so rosy in the cradle
but I’ll be a friend, I’ll tell you what’s in store
There’s nothing at the end of the rainbow
There’s nothing to grow up for anymore"
posted by omnidrew at 7:06 AM on September 22, 2005

"Street Car" by Hayden.
"Beach Music" by the Watchmen.
"Nautical Disaster" by the Tragically Hip.
"Left and Leaving" by the Weakerthans.
"Nothing Gets Crossed Out" by Bright Eyes.
"The Chalet Lines" and "Take Your Carriage Clock and Shove It" by Belle & Sebastian.
posted by Johnny Assay at 7:06 AM on September 22, 2005

"We All Fall in Love Sometimes" by Jeff Buckley
"Best of Me" by American Football
"Lonelily" by Damien Rice
"Non-Believer" by Joel Plaskett (local maritime singer/songwriter)
"Can't You See" by The Marshall Tucker Band
"Carry Me Ohio" by Sun Kil Moon
posted by dflemingdotorg at 7:06 AM on September 22, 2005

Alkaline Trio - Sorry About That
posted by cheerleaders_to_your_funeral at 7:17 AM on September 22, 2005

I second "I'm So Lonesome, I Could Cry," though one version that hurts for me--laugh if you must--is a live cut by Elvis Presley. There's a lot of pain in the singing of it due probably to his feeling isolated and alone. This, of course, would've been after he divorced Priscilla and lost custody of Lisa Marie. Look for it on say, "An Afternoon in the Garden," or another live 70's era recording.
posted by TN_Tanuki at 7:26 AM on September 22, 2005

Back to the Old House -- the Smiths.
posted by chunking express at 7:31 AM on September 22, 2005

"Ruby's Arms" by Tom Waits.
posted by transient at 7:33 AM on September 22, 2005

Adagio for Strings, Op. 11 by Barber.
While I agree that this is very, very sad, it's so exquisite that I almost can't be sad while listening to it. Also, there's a bit of...hope, toward the end.

"Lover, You Should Have Come Over", by Jeff Buckley.
Oh, yes. I agree with so many of the above, so I tried to only mention those songs/versions that haven't yet been posted:

“We’re Just Friends”—Wilco
“A Song For You”—Donny Hathaway
“Ne Me Quitte Pas”—esp. the Nina Simone version
“Dangling Conversations”—Simon & Garfunkle
“Sweeter For Me”—Joan Baez
“I Never Dreamed You’d Leave In Summer”—I think the Joan Baez cover has the edge here, but the Stevie Wonder original is great, too.
“Lately”—Stevie Wonder
“My Old Flame”—John Vanderslice
“The First Time Ever I Saw Your Face”—Robert Flack
“Ain’t No Way”—Aretha Franklin
“I’ve Been Loving You Too Long”—Otis Redding? Aretha? Too hard to say which is sadder.
posted by CiaoMela at 7:37 AM on September 22, 2005

"Inncoent When You Dream" Tom Waits (someone already mentioned another song from this Album, Frank's Wild Years; it veers bewteen mania and melancholy throughout.
“Here Comes the Flood” by Peter Gabriel
"Carmelita" by Warren Zevon. Also, "Don't Let Us Get Sick"
"Atlantic City" by Bruce Springsteen.
"Home on the Range" by Tori Amos
"Bury Me" by Dwight Yokham (nor intended to be sad, yet it always causes tears to well up for me.
"The Last Time I Saw Richard" and "Little Green" by Joni Mitchell
"I see a Darkness" as covered by Johnny Cash
"Helpless" Neil Young (and a recent cover by kd Lang)
"Minor Incident" - Badly Drawn Boy
posted by Verdant at 7:38 AM on September 22, 2005

Townes Van Zandt -- "Tecumseh Valley", "Waiting Around to Die", "Lungs", "Rex's Blues" and many, many others.
posted by barjo at 7:44 AM on September 22, 2005

'Walking in the Sun,' Percy Sledge
'Dead Homiez,' Ice Cube
'Mary Don't You Weep,' Aretha Franklin
'Patches,' Clarence Carter
posted by box at 7:44 AM on September 22, 2005

Eric Bogle's "The Band Played 'Waltzing Matilda'" (I like the Pogues version)
Otis Redding's "Fa-Fa-Fa-Fa-Fa (Sad Song)"
posted by kirkaracha at 7:45 AM on September 22, 2005

Beck - The Golden Age.
Billy Bragg - Tank Park Salute
posted by docpops at 7:48 AM on September 22, 2005

"Nobody knows me (like my baby)" by Lyle Lovett, although it's soulful till the last verse when it becomes heartbreaking.

Amusingly I once saw it on the "wedding album" of a couple who clearly didn't listen past the first verse. Or perhaps it was a warning from the bride to the groom that if he succumbed to temptation and banged some Mexican whore she's leave him too.
posted by phearlez at 7:50 AM on September 22, 2005

A lot of stuff by John Prine, but particularly "Sam Stone" and "Hello in There"; can't believe nearly a hundred replies into this, I'm the first to mention John Prine...
posted by paulsc at 7:51 AM on September 22, 2005

"Oh My Sweet Carolina" by Ryan Adams
"Brick" or "Don't Change Your Plans" by Ryan Adams
"Leaving on a Jet Plane" by Peter Paul and Mary (yes really)
"Lost My Driving Wheel" by Cowboy Junkies

And the following by Tom Waits:
"Alice," "Come on Up to the House," "Shiver Me Timbers," and "Fish and Bird."
posted by hamster at 7:52 AM on September 22, 2005

"Knockin' on Heaven's Door", from Warren Zevon's last album.
posted by SteveInMaine at 7:59 AM on September 22, 2005

"Nobody knows me (like my baby)" by Lyle Lovett, although it's soulful till the last verse when it becomes heartbreaking.

Amusingly I once saw it on the "wedding album" of a couple who clearly didn't listen past the first verse. Or perhaps it was a warning from the bride to the groom that if he succumbed to temptation and banged some Mexican whore she's leave him too.
posted by phearlez

My S.O. and I are looking at including several of Lyle's songs on a wedding disc, precisely because his gallows humor and irony nicely highlight the frailties and the possible consequences of the endeavor. Kind of a downer, but we both enjoy songs that exorcise emotions of pity and terror.
posted by Verdant at 7:59 AM on September 22, 2005

"Half a World Away", REM (actually, that whole album just kills me)
"Blood and Fire", Indigo Girls
"She Says", Ani Difranco
"Jezebel", 10,000 Maniacs

And the one song I absolutely cannot ever listen to without dissolving into a puddle of goo (and which has already been mentioned) is Eric Clapton's "Tears in Heaven".

On the other hand, Smiths and Morrissey songs cheer me right up.
posted by eilatan at 8:18 AM on September 22, 2005

"Oh Comely" by Neutral Milk Hotel is brutally sad.

Indeed. That or perhaps Two Headed Boy Pt. II. Both have been known to make me cry.

Also:

"Nobody Loves You When You're Down and Out" - John Lennon
(Not to be confused with the old blues song, "Nobody Knows You When You're Down and Out")
"Thirteen Months in Six Minutes" - The Wrens
"Dead Slate Pacific" - John Vanderslice
posted by ludwig_van at 8:18 AM on September 22, 2005

"Me and Your Sister" by This Mortal Coil. Sung by Kim Deal and Tanya Donnelly.
posted by erebora at 8:29 AM on September 22, 2005

"The Jeweler" - Pearls Before Swine
"This One's Gonna Bruise" - Beth Orton
"Stay With Me" - Lorraine Ellison
"The Sound Of Someone You Love Who's Going Away And It Doesn't Matter" - Penguin Cafe Orchestra
"(On Tuesdays She Used To Do) Yoga" - Peter Hammill (from the deliberately cathartic "Over" album)
"Time In The Son" - Eliza Carthy
"Watching You Without Me" - Kate Bush
"I Am The Cosmos" - Chris Bell
"Gloomy Sunday" - lots of people, but I kinda like Heather Nova's version
"John Wayne Gacy" - Sufjan Stevens
"As You Turn To Go" - the 6ths
posted by Captain Swing at 8:48 AM on September 22, 2005

Dirty Three - I Really Should Have Gone Out Last Night
posted by shinji_ikari at 8:48 AM on September 22, 2005 [1 favorite]

Bob Dylan-Spanish Boots of Spanish Leather
Barber-Addagio for Strings
posted by chrismc at 9:05 AM on September 22, 2005

"I am a Rock" S & G (and lots more by them)
posted by artifarce at 9:11 AM on September 22, 2005

Louise by Leo Kottke and Bonnie Raitt

It's about a hooker who commits suicide.

Well they all said Louise was not half bad
It was written on the walls and window shades
And how she'd act the little girl
A deceiver, don't believe her that's her trade
Sometimes a bottle of perfume,
Flowers and maybe some lace
Men brought Louise ten cent trinkets
Their intentions were easily traced
Yes and everybody knew at times she cried
But women like Louise they get by

Well everybody thought it kind of sad
When they found Louise in her room
They'd always put her down below their kind
Still some cried when she died this afternoon
Louise rode home on the mail train
Somewhere to the south I heard it said
Too bad it ended so ugly,
Too bad she had to go this way
Ah but the wind is blowing cold tonight
So good night Louise, good night
posted by wsg at 9:11 AM on September 22, 2005

Pale Shelter - Tears for Fears
posted by black8 at 9:23 AM on September 22, 2005

"Down to Seeds and Stems Again Blues" -- Commander Cody
posted by maurice at 10:06 AM on September 22, 2005

For driving and crying:
* Carmelita / Dwight Yoakam
* Red Dirt Girl / Emmylou Harris
* Orphan Girl / Gillian Welch
* Tecumsah Valley / Steve Earle's version
* Almost Blue / Elvis Costello
* In My Life / Johnny Cash's version
* Landslide / Dixie Chicks
* This Shirt / Mary Chapin Carpenter
* Goodbye / Steve Earle
* Jackson / Lucinda Williams
* Wild Horses / Rolling Stones
* Dead Flowers / Townes Van Zandt

My DH calls it the "Holy shit, why not just slit your wrists now?" mix.
posted by MonkeyToes at 10:12 AM on September 22, 2005

I'd have to second "I really should have gone out last nigh", even though an instumental, it always cuts me up.

I almost always get dead sad listening to Nick Drake, for fairly obvious reasons.

Cure's "Disintegration" is an incredibly sad album.
posted by doozer_ex_machina at 10:24 AM on September 22, 2005

Versus "Crazymaker" and "Morning Glory"
Elliot Smith "Pitselah"
Bright Eyes "At The Bottom of Everything"
Violent Femmes "Country Death Song"
Radiohead "Creep"
posted by Sara Anne at 10:25 AM on September 22, 2005

R.E.M.'s instrumental version of "Last Date" is very sad and pretty.
posted by kirkaracha at 10:39 AM on September 22, 2005

The saddest songs, for me are where my time and place connect to the lyrics, which is not to say that particular chord progressions, or kinds of progressions, and tempos don't encourage it all, of course. A couple of these selections are here because just part of the song is the saddest ever, but so sad that they must be included.

Consider any repeats a hearty second, I only quickly scrolled through the other answers:

Joy Division: Love will Tear Us Apart, Atmosphere, She's Lost Control
Tom Waits: Hope I Don't Fall In Love With You [and many other songs off of The Early Years Vol. 2: In between love, I want you, etc.]
Gillian Welch: Elvis Presley Blues
Cat Stevens: I can't even listen to Cat Stevens anymore to the point where I've blocked the song titles from memory. I think it's me more than him.
Slint: Good Morning, Captain
Cat Power: I Don't Blame You, and more Good Woman, etc. from You are Free.
Nina Simone: Wild is the Wind, Four Women [MY NAME IS PEACHES!!! -- amazing]
Can: Thief
Low: Time is the Diamond
Neil Young: Tonight's the Night, Round & Round, The Needle and the Damage Done.
Silkworm: Raised by Tigers [especially the acoustic version]
Joel R. L. Phelps: All We Want, Warm Springs, Night, There is Not Enough -- all from the consistently heartbreaking Warms Springs Night.
Built to Spill: Nowhere Nothin' F*ckup
The Afghan Whigs: Let Me Lie To You. My Curse
Elliott Smith: 2:45am For different reasons than Cat Stevens, I can barely listen to any Elliot Smith anymore.
Buffalo Tom: Taillights Fade, I'm Not There, Saving Grace [all from: Let me come Over -- though these songs are a little less affecting than they used to be.]
Cadallaca: Your One Wish, O Chenilla
Carol King: So far Away it just slays me now that I live far away from so many loved ones.
Fugazi: Rend It from In on the Killtaker
Chappaquiddick Skyline: Everyone Else is Evolving, The Two of You Sleep, Solitary Swedish Houses.
Codiene: Loss Leader, Vacancy
Elvis Costello: Alison
Minutemen: History Lesson - Part II
Pinebender: simp twister
Mountain Goats: The Best Ever Death Metal Band In Denton, Color in Your Cheeks, Going to Georgia
Minor Threat: Salad Days. Seriously.
Rights of Spring: End On End.
Sebadoh: Everybody's Been Burned
Steve Earle: Christmas In Washington
Sufjan Stevens: John Wayne Gacy, Jr. -- perhaps this is just depressing.
Sunny Day Real Estate: Seven. In Circles
Giant Sand: (Well) Dusted (For The Millennium). A slight return...
posted by safetyfork at 10:40 AM on September 22, 2005 [1 favorite]

"Dearly Departed" by Devotchka.
posted by exceptinsects at 10:44 AM on September 22, 2005

Stella Blue - Grateful Dead
posted by gnz2001 at 10:45 AM on September 22, 2005

Tom Waits, live version of "Cold, Cold Ground."
posted by robocop is bleeding at 10:52 AM on September 22, 2005

How Much I Feel - Ambrosia

I don't know how this whole business started
Of you thinking that I have been untrue
But if you think that we'd be better parted
It's gonna hurt me but I'd break away from you
Well just give me the sign and I will be gone

That's how much I feel for you baby
How much well I need your touch
How much I live I live for your loving
That's how much that's how much that's how much

Sleep alone and late at night I am dreaming
Of the togetherness that seems to leaving me oh no
It ain't long then I kiss some more
If you'll only love me like you have before
Ahh take hold of my hand I will be forgiven

That's how much I feel feel for you baby
How much I need your touch
How much I live for your loving
That's how much that's how much that's how much

So you try to stay in the middle
And then cry - cry just a little
Then we both realize how foolish you been
I've been trying to make amends
But your pulling all the strings
'Cause that's how much - that's how much
That's how much

How's your life been going on
I got a wife now years we been going strong
Oh no there's just something I got to say
Sometimes when we make love I still see your face
Just try to recall when we were as one yeah

That's how much I feel for you baby
How much I need I need your touch
How much I live I live for your loving
posted by terrier319 at 11:03 AM on September 22, 2005

"Sharp Cutting Wings" by Lucinda Williams.
posted by Verdant at 11:08 AM on September 22, 2005

Tori Amos - Mother
Van Morrison - Into the Mystic
Israel Kamakawiwo'ole - Somewhere Over the Rainbow/Wonderful World
posted by peep at 11:41 AM on September 22, 2005

"Sara" -- Bob Dylan. Saddest. Breakup Song. Ever. (after you find out it was his last-ditch, failed effort to salvage a not-that-short marriage with his then-estranged wife.)

"Long Black Veil"--Johnny Cash.
"Hurt"--Johnny Cash version.
posted by availablelight at 11:46 AM on September 22, 2005

I don't do lyrics so well, so some of these suggestions may be off base. (I hear Cadallaca's "Winter Storm '98" and I don't think "sad," for example.)

I'm surprised there isn't more Dirty Three on this list; they've always done melancholy well. "Lullabye for Christie," off the same album as "I Really Should've Gone Out Last Night" (Whatever You Love, You Are) is my favourite; one of my friends called it a funeral dirge, and that seems about right. All of Ocean Songs fits this category as well.

Sarah Harmer has a couple that seem to fit the bill: "Capsized," "Lodestar," "Tether," "Coffee Stain." Neko Case's Canadian Amp EP is hard to find but full of little gems like "In California" (originally by Lisa Marr) and "Knock Loud" (originally by Sook-Yin Lee). Then there's "I Wish I Was The Moon" off Blacklisted.
posted by chrominance at 11:47 AM on September 22, 2005

Calexico and Iron&Wine : Dead Man's Will
posted by u2604ab at 11:47 AM on September 22, 2005

Oh, one more: "Feel To Believe," Beth Orton.
posted by chrominance at 11:48 AM on September 22, 2005

Oh yeah; I second Dar William's "When I was a boy"
posted by u2604ab at 11:48 AM on September 22, 2005

on preview: a second for Dylan's "Boots of Spanish Leather" too, as suggested by chrismc.
posted by availablelight at 11:49 AM on September 22, 2005

'Sara'
Bob Dylan

I laid on a dune, I looked at the sky,
When the children were babies and played on the beach.
You came up behind me, I saw you go by,
You were always so close and still within reach.

Sara, Sara,
Whatever made you want to change your mind?
Sara, Sara,
So easy to look at, so hard to define.

I can still see them playin' with their pails in the sand,
They run to the water their buckets to fill.
I can still see the shells fallin' out of their hands
As they follow each other back up the hill.

Sara, Sara,
Sweet virgin angel, sweet love of my life,
Sara, Sara,
Radiant jewel, mystical wife.

Sleepin' in the woods by a fire in the night,
Drinkin' white rum in a Portugal bar,
Them playin' leapfrog and hearin' about Snow White,
You in the marketplace in Savanna-la-Mar.

Sara, Sara,
It's all so clear, I could never forget,
Sara, Sara,
Lovin' you is the one thing I'll never regret.

I can still hear the sounds of those Methodist bells,
I'd taken the cure and had just gotten through,
Stayin' up for days in the Chelsea Hotel,
Writin' "Sad-Eyed Lady of the Lowlands" for you.

Sara, Sara,
Wherever we travel we're never apart.
Sara, oh Sara,
Beautiful lady, so dear to my heart.

How did I meet you? I don't know.
A messenger sent me in a tropical storm.
You were there in the winter, moonlight on the snow
And on Lily Pond Lane when the weather was warm.

Sara, oh Sara,
Scorpio Sphinx in a calico dress,
Sara, Sara,
You must forgive me my unworthiness.

Now the beach is deserted except for some kelp
And a piece of an old ship that lies on the shore.
You always responded when I needed your help,
You gimme a map and a key to your door.

Sara, oh Sara,
Glamorous nymph with an arrow and bow,
Sara, oh Sara,
Don't ever leave me, don't ever go.


Copyright © 1975 Ram's Horn Music
posted by availablelight at 11:55 AM on September 22, 2005

Molly Malone
posted by Human Flesh at 12:02 PM on September 22, 2005

Did anyone mention "Fast Car" by Tracy Chapman yet?
posted by availablelight at 12:14 PM on September 22, 2005

Dvorak's New World Symphony. Beautiful and heartbreaking.
posted by cptnrandy at 12:22 PM on September 22, 2005

I second John Prine:
There's a hole in Daddy's arm where all the money goes
Jesus died for nothing, I suppose
posted by sonofsamiam at 12:31 PM on September 22, 2005

these are the saddest songs i can think of:

bright eyes - padraic my prince
pedro the lion - the longest winter
posted by mayfly wake at 12:49 PM on September 22, 2005

Billie Holliday - Gloomy Sunday (was once known as the suicide song and radio stations were not allowed to play it excpet at certain times of day)

Nina Simone - Several I can think of, but they've already been covered here.

Julie London (or anyone else) - Cry Me a River

Hoagy Carmichael or Allison Eastwood's recordings of Skylark.
posted by monopas at 1:45 PM on September 22, 2005

Coat of Many Colors - Dolly Parton

Upward Over the Mountain - Iron & Wine
"Mother remember that night that the dog had her pups in the pantry
Blood on the floor, fleas on their paws and you cried 'til the morning"

Same Old Lang Syne - Dan Fogelberg
Just for a moment I was back at school
And felt that old familiar pain
And as I turned to make my way back home
The snow turned into rain --

also, perhaps for purely personal reasons since it makes me homesick:

Hills of West Virginia - Phil Ochs
posted by macinchik at 2:37 PM on September 22, 2005

"two of us"- the beatles (from let it be)
posted by martinX's bellbottoms at 5:24 PM on September 22, 2005

"Something I Can Never Have", Nine Inch Nails, from CRC Sessions or Still (voice and piano version)
"Lover's Spit", Broken Social Scene, especially the alternate version from Bee Hives
"Hey Man (Now You're Really Living)", Eels -- which is a deceptively happy song, until you really listen to it
"When the Night Comes Falling From the Sky", Bob Dylan, Empire Burlesque -- the best song off a so-so album
"Divorce Song" and "Shatter", Liz Phair
"Maps", Yeah Yeah Yeahs (p.s. good cover by Arcade Fire)
"The Fall of the World's Own Optimist", "Nothing Is Good Enough", "It's Not", "Real Bad News", etc. by Aimee Mann (who does a decent cover of "The Scientist", but you're probably thinking more of her cover of "One (Is the Loneliest Number)")
"Missed Me", Dresden Dolls
"Rebellion (Lies)", Arcade Fire, or "Neighborhood #1 (Tunnels)" or "In the Back Seat"
"Here Comes the Rain Again", Eurythmics, or "Would I Lie to You?"

Now for some obscurities:
"Someday We'll Understand", Animal Logic
"Twist in My Sobriety" and "World Outside Your Window", Tanita Tikaram (who has many even sadder songs, but these are better known and accessible)
"Are You Gonna Miss Me", Anna Fermin's Trigger Gospel
"Dead Road 7", The Kills (or several others)

But what do I know? Once upon a time, "Careless Whisper" got to me ....
posted by dhartung at 9:19 PM on September 22, 2005 [1 favorite]

One more, for posterity (if posterity still reads AskMe):

"The Perfect Fit" by The Dresden Dolls. Knocks me down every time.
posted by dhartung at 1:06 PM on September 24, 2005

Did anyone mention "Fast Car" by Tracy Chapman yet?

No, but they should. Excellent entry.
posted by weston at 1:39 AM on September 26, 2005

"Casimir Pulaski Day" by Sufjan Stevens.
"Winter" by John Radin
"Photographs and Memories" by Jim Croce
"Pinstripe (acoustic)" by Something for Kate (a good example of cathartically sad, this one)

A few songs that I've got to second are "Here Comes the Flood" by Peter Gabriel, "E Lucevan Le Stelle" from Puccini's Tosca, and "Last Goodbye" by Jeff Buckley.

"Day After Tomorrow" by Tom Waits is absolutely unbearable when you're missing someone. In fact, there are a lot of songs that become tragically sad when you're missing someone.
posted by teem at 9:26 AM on September 30, 2005

"Hallelujah" by Nick Cave (completely different song to the Leonard Cohen song)
posted by slightlybewildered at 11:27 PM on September 30, 2005

I have to mention David Byrne's Last Emporer Theme and pretty much all of Emmylou Harris' masterpiece Wrecking Ball album, especially Where Will I Be?, Going Back to Harlan, All My Tears, and This Sweet Old World. Some of Patsy Cline's songs, such as Walking After Midnight and I Fall To Pieces are pretty sad too.
posted by blue shadows at 4:32 PM on October 1, 2005

"Two Beds And A Coffee Machine" - Savage Garden

"Where You Wanted To Be" - Darren Hayes

They get to me everytime.
posted by divabat at 6:04 AM on October 7, 2005

Deceptively depressing title, "Beautiful" - James Blunt.

Always tear up at "Fire and Rain" - James Taylor.

And along the same lines, "One Moment More" - Mindy Smith.

And Lucinda Williams, "World Without Tears" but especially "Words Fell". Longing for the love that you cannot touch but is remembered from another ancient time.
posted by Kusum at 1:13 PM on October 16, 2005

PJ Harvey and Thom Yorke - This Mess We're In
posted by dazed_one at 9:43 PM on March 19, 2006

Yo La Tengo - "Tears Are in Your Eyes"

Phew...
posted by AwkwardPause at 10:29 AM on March 20, 2006

What teem said... missing someone makes a whole mess of songs sad.

I second 'Shannon' by Henry Gross... and staying in the losing-a-pet-vein, I'll add Alan Parsons' 'The Very Last Time,' written by Ian Bairnson about his dog Gemma, sung by Beverley Craven.

and I'll say that Ambrosia's contribution to sad, that surpasses 'How Much I Feel,' listed above, is 'Holdin' On To Yesterday.'

But I'll add:

'Diary' - Bread Yep, Bread. Can't even get through the song without tears. Even when I was 12.

But then, I'm a basketcase these days...
posted by OneOliveShort at 8:17 PM on March 21, 2006