The 25 Most Exquisitely Sad Songs in the Whole World

[GothicRavenGoddess (3)]

The 25 Most Exquisitely Sad Songs in the Whole World

There's no shortage of sad songs about rainy days and lovers who don't bring flowers. And then there are songs that truly bring the pain -- songs so despairing they can make us wonder why we even bother. Here are 25 little ditties so crushing, they could knock Dick Cheney to his knees.

25:'The River' Bruce Springsteen (1980)

The Breakdown: Premature pregnancy, marriage and a weepy harmonica crush the dreams of a young couple.

The Waterworks: "We went down to the courthouse/And the judge put it all to rest/No wedding day smiles, no walk down the aisle/No flowers, no wedding dress."

Casualty Count: One couple's age of innocence.

24:'Nothing Compares 2 U' Sinead O'Connor (1990)

The Breakdown: In this Prince-penned purple ode to an incomparable ex, there is life after love, but life really sucks.

The Waterworks: "Nothing can stop these lonely tears from falling/Tell me baby, where did I go wrong?"

Casualty Count: One lover, seven hours, fifteen days.

23:'No Surprises' Radiohead (1997)

The Breakdown: A killer even by Thom Yorke's bleak standards, the kiddie chimes can't hide the singer's suicidal depression.

The Waterworks: "I'll take a quiet life/A handshake, some carbon monoxide."

Casualty Count: One heart that's "full up like a landfill."

22:'A Change Is Gonna Come' Sam Cooke (1964)

The Breakdown: Recorded just before his tragic death, the soul great's response to 'Blowin' in the Wind' set the tone for the desperate Civil Rights struggle.

The Waterworks: "It's been too hard living, but I'm afraid to die."

Casualty Count: Countless proud citizens in Jim Crow America.

21:'Space Oddity' David Bowie (1969)

The Breakdown: In the same year as our lunar landing, rock's space alien creates Major Tom, whose remains will travel the galaxy alone forever.

The Waterworks: "Tell my wife I love her very much."

Casualty Count: One astronaut.

20:'That's the Way I've Always Heard It Should Be' Carly Simon (1971)

The Breakdown: Marriage is inevitably dismal in this evocative pop hit, which was recorded a year before Simon's ill-fated marriage to James Taylor.

The Waterworks: "Their children hate them for the things they're not/They hate themselves for what they are."

Casualty Count: All marriages, one American

19:'Lost Cause' Beck (2002)

The Breakdown: The postmodern trickster reaches back to the Romantic era for the most depressing song on his breakup album, 'Sea Change.'

The Waterworks: "I'm tired of fighting/Fighting for a lost cause."

Casualty Count: The one love of your life.

18:'I've Gotta Get a Message to You' Bee Gees (1968)

The Breakdown: Condemned man makes final plea to loved one.

The Waterworks: "One more hour and my life will be through."

Casualty Count: One convicted murderer with a heart of gold.

17:'Back to Black' Amy Winehouse (2006)

The Breakdown: An ominous song of impending misery following infidelity, sung by a woman with her departing lover's name tattooed on her chest.

The Waterworks: "You go back to her/And I go back to black."

Casualty Count: A lover. Sobriety? Sanity?

16:'Shilo' Neil Diamond (1968)

The Breakdown: Lonely kid turns to an imaginary friend.

The Waterworks: "Papa says he'd love to be with you/If he had the time."

Casualty Count: One squandered father-son relationship

15:'My Mom' Chocolate Genius (1998)

The Breakdown: Recent Springsteen sideman cut this heart breaker about a return visit to his childhood home, and the mother he was losing to senility.

The Waterworks: "My mom, my sweet mom/She don't remember my name."

Casualty Count: One Alzheimer's victim (and one dog).

14:'Anyone Who Had a Heart' Dionne Warwick (1963)

The Breakdown: A lover begs her man to see how he's mistreating her. Classic Bacharach/David melodrama, crushing Warwick wails.

The Waterworks: "What am I to do?"

Casualty Count: One lover's sense of pride.

13:'Naked as We Came' Iron & Wine (2004)

The Breakdown: Indie folkie Sam Beam's brutally sweet love song acknowledging that one always has to die before the other, plus a plug for cremation.

The Waterworks: "If I leave before you, darling/Don't you waste me in the ground."

Casualty Count: Your better half.

12:'In the Wee Small Hours of the Morning' Frank Sinatra (1954)

The Breakdown: Ol' Blue Eyes parlayed his painful divorce from movie star Ava Gardner into a career makeover: the lonely guy at the end of the bar.

The Waterworks: "You'd be hers if only she would call."

Casualty Count: One Hollywood marriage, countless nights of sleep.

11:'Brick' Ben Folds Five (1997)

The Breakdown: Singer recalls taking his high-school girlfriend to get an abortion -- on the day after Christmas, no less.

The Waterworks: "Now that I have found someone/I'm feeling more alone/Than I ever have before."

Casualty Count: One pregnancy, one first love, several Christmas presents.

10:'In the Real World' Roy Orbison (1989)

The Breakdown: The master of pop-opera misery ('Crying,' 'It's Over') outdid himself with this quavering answer to his own 'In Dreams.' Posthumously released.

The Waterworks: "I love you and you love me/But sometimes we must let it be."

Casualty Count: All dreams.

09:'Concrete Angel' Martina McBride (2001)

The Breakdown: What's more devastating than a child's headstone?

The Waterworks: "A name is written on a polished rock/A broken heart that the world forgot."

Casualty Count: One victim of child abuse.

08:'Dance With My Father' Luther Vandross (2003)

The Breakdown: Impossibly wrenching lament for the fact that we can't take care of our kids forever.

The Waterworks: "Sometimes I'd listen outside her door/And I'd hear how my mother cried for him/I'd pray for her even more than me."

Casualty Count: One father, one boy's sense of security in his father's arms

07:'Hallelujah' Jeff Buckley (1994)

The Breakdown: Leonard Cohen's existential hymn addressing an old fling becomes a heavenly, if unanswered, prayer in the hands of the ill-fated Buckley.

The Waterworks: "Love is not a victory march/It's a cold and it's a broken Hallelujah."

Casualty Count: One crisis of faith.

*06:'He Stopped Loving Her Today' George Jones (1980)

The Breakdown: Sung by the country star with the most tears in his beer this side of Hank Sr., a jilted lover carries his old flame's memory until his dying day.

The Waterworks: "I went to see him just today/Oh, but I didn't see no tears/All dressed up to go away/First time I'd seen him smile in years."

Casualty Count: One fatally broken heart.

05:'I Know It's Over' The Smiths (1986)

The Breakdown: For Morrissey, the world's loneliest singer, life isn't just over -- it never really began.

The Waterworks: "As I climb into an empty bed/Oh, well, enough said."

Casualty Count: One lonely soul ... any minute now.

04:'Hurt' Johnny Cash (2002)

The Breakdown: In failing health, the great American singer tolls a death knell for the rest of us with this brutal Nine Inch Nails song about addiction and self-destruction.

The Waterworks: "And you could have it all/My empire of dirt/I will let you down/I will make you hurt."

Casualty Count: Everyone he knows ("goes away in the end").

03:'Eleanor Rigby' The Beatles (1966)

The Breakdown: The cute Beatle writes a timeless, devastating ode to the futility of life, set to a grieving string octet.

The Waterworks: "Eleanor Rigby died in the church and was buried along with her name/Nobody came."

Casualty Count: One spinster, one pair of socks.

02:'Gloomy Sunday' Billie Holiday (1941)

The Breakdown: The Queen of Soul-Sapping is haunted about losing a loved one.

The Waterworks: "Angels have no thought of returning you/Would they be angry if I thought of joining you?"

Casualty Count: One woman's will to live.

01:'Chicken Wire' Pernice Brothers (1998)

The Breakdown: Breathy Massachusetts sad sacks offer a lovely ballad about a woman choking to death on exhaust fumes ... and a cloud of minor chords.

The Waterworks: "They found her car/Still running/In the garage."

Casualty Count: One woman, and the drink she was holding.

*This is the saddest of them all, I think.... What song chokes you up, no matter what mood you are, when you listen to it? What songs do you avoid, when you are sad, because you know it will make you cry?

Some on here fit the bill.. There are several other's that aren't on here that always make me cry.

What's your crying shame?

Edited July 28, 2009 by GothicRavenGoddess

[phee]

Sad songs to phee.... hmmm

Not in any order but

- 30kft by Assemblege 23

- Slateman by Godflesh

- Yellowstone by Tangerine Dream

- La petite fille de la mer by Vangelis

- Dail Out by Vangelis

- Precious by Depeche Mode

[jynxxxedangel]

Gloomy Sunday--Billie Holiday

Mary of the Wild Moor--Johnny Cash

Edited July 28, 2009 by jynxxxedangel

[Rev.Reverence]

David Bowie was not "Ziggy Stardust" till AFTER that album, he donned the persona in '71 through '73.

SEE, here's the video (from 1969):

[jynxxxedangel]

[Msterbeau]

No Joy Division's "Love will Tear us Apart???

Fail.

[pomba gira]

No Joy Division's "Love will Tear us Apart???

Fail.

That one's not sad, just depressing.

Johnny Cash "Hurt"... especially if you watch the video.

Metallica "Fade to Black"

Billie Holliday "Strange Fruit"

[jynxxxedangel]

This one has always torn me up. Something about the harmony, and the lyrics combined. I love the Louvin Brothers.

Also, just about any song by Ernest Tubb. His voice, and the songwriters' magic. He can break my heart within three notes.

Yes, I'm an old hillbilly. So shoot me.

P.S. YES, Hille. I was going to post "Strange Fruit." That one gives me the shivers to hear. I can barely stand it.

A small bit of trivia..Billie Holiday and her band were once banned from performing at the Fox Theater, because her band was interracial. Back in those days, it was very frowned upon to have band members of multiple races. How very bigoted things were, back in the 1930s and 1940s

Edited July 28, 2009 by jynxxxedangel

[Simon Bar Sinister]

we have a winner

[jynxxxedangel]

http://www.youtube.com/watch?v=NNre5neZ6QI

This one has a lot of personal meaning for me.

[Rev.Reverence]

Johnny Cash "Hurt"... especially if you watch the video.

Oddest thing about that song is...it's a NIN tune...HE covered Trent

...BUT...near everyone I have heard talkin' about it in the past few months (QUITE A FEW) thought it was Johnny's own stuff

(even some dumb kid I just saw on youtube playing Hurt lists it as a Johnny Cash cover)

...but, knowing what it is about (all to well)...it is a sad happening no matter who sings it.

http://www.youtube.com/watch?v=iFx2TmQfM-o

[TheOsakaKoneko]

No Joy Division's "Love will Tear us Apart???

Fail.

Yep.

Also, VNV Beloved and Wolfsheim Once in a Lifetime...goddamn sad songs being #1 dance floor hits.. >< I don't like it. But I do like dancing to love will tear us apart...

Though Beloved grew on me after the Cleveland concert..

[pomba gira]

P.S. YES, Hille. I was going to post "Strange Fruit." That one gives me the shivers to hear. I can barely stand it.

A small bit of trivia..Billie Holiday and her band were once banned from performing at the Fox Theater, because her band was interracial. Back in those days, it was very frowned upon to have band members of multiple races. How very bigoted things were, back in the 1930s and 1940s

Yup... she very often couldn't stay in the same hotel as the band, either.

Oddest thing about that song is...it's a NIN tune...HE covered Trent

...BUT...near everyone I have heard talkin' about it in the past few months (QUITE A FEW) thought it was Johnny's own stuff

(even some dumb kid I just saw on youtube playing Hurt lists it as a Johnny Cash cover)

Prolly 'cos it's so unusual for a long-established artist to cover a younger one's material. But Johnny Cash did it quite often. NIN, Nick Cave, Soundgarden... I really admired that about the Man in Black.

[Shade Everdark]

Yep.

Also, VNV Beloved and Wolfsheim Once in a Lifetime...goddamn sad songs being #1 dance floor hits.. >< I don't like it. But I do like dancing to love will tear us apart...

Though Beloved grew on me after the Cleveland concert..

Interesting. I always 'hear' Once in a Lifetime as either angry or resolute. The narrator, if you will, sounds angry, and resolute. At least to my ears.

That said, on the subject of Wolfsheim, a song introduced to me by the lovely Nienna--Old Man's Valley. Might has well have a razor on hand when you listen to that one.

And holy crap, 3/4 of Loreena McKennitt's entire body of work.

[TheOsakaKoneko]

Interesting. I always 'hear' Once in a Lifetime as either angry or resolute. The narrator, if you will, sounds angry, and resolute. At least to my ears.

That said, on the subject of Wolfsheim, a song introduced to me by the lovely Nienna--Old Man's Valley. Might has well have a razor on hand when you listen to that one.

And holy crap, 3/4 of Loreena McKennitt's entire body of work.

I love that song by Wolfsheim.

Sure the other is resolute, but it's still about losing his wife and son. Damn. The video is really super sad too.

[MarsDustDoug]

the entire "Spiceworld" album by the spice girls

gets me everytime....

[the eternal]

That one's not sad, just depressing.

Johnny Cash "Hurt"... especially if you watch the video.

Metallica "Fade to Black"

Billie Holliday "Strange Fruit"

GREAT CHOICES!

For me, the mood of the music HAS to match the sadness of the lyrics.

I remember Toad the Wet Sprocket bitching in interviews about the audience reaction when they played "Hold Her Down"

To which I reply "Then don't make a song about rape you can dance to!

Tying both of those subjects together in a bow---

Tori Amos --Me and a Gun

More songs off the top of my head

Joy Division --

--The Eternal

--Atmosphere

Pearl Jam

--Black

Nick Drake

--Way to Blue (Honestly, it's the lush melancholy of the opening that gets me every time)

--Parasite (although anything off Pink Moon would work, this one really gets to me)

Frank Sinatra

--What's New (although anything off his two "suicide albums" In the Wee Small Hours or Only the Lonely would work)

The Cure

--Closedown (although I kinda view the entire Disintegration album as one 'most exquisitely sad song')

Violent Femmes

--There's Nothing Worth Living For

Anytime I hear Michael Bolton sing, I get exquisitely sad and angry at the same time.

[Rev.Reverence]

You WANT sad..?..um, here ya' go!

http://www.youtube.com/watch?v=H2vguoy2aAY

[Rev.Reverence]

...shit...not done cryin' yet...these'll jerk some tears...

Edited July 30, 2009 by Rev.Reverence

[jynxxxedangel]

http://www.youtube.com/watch?v=RDCZCCQVbRs

http://www.youtube.com/watch?v=EOuhrCRfQJA

[jynxxxedangel]

Edited July 30, 2009 by jynxxxedangel

[jynxxxedangel]

http://www.youtube.com/watch?v=jauOlgUZL4A

Great cover of an Alan Parsons Project song.

Edited July 30, 2009 by jynxxxedangel

[Simon Bar Sinister]

we have a winner

...and a strong 2nd-place finisher:

[jynxxxedangel]

http://www.youtube.com/watch?v=aEaIL26dN4c

This one's a killer. If it doesn't make you cry, you have no heart.

[Scales]

Blue, the song from the end of Cowboy Bebop. (Vid is graphic.)

Edited July 31, 2009 by Scales