Posted May 3rd 2007 7:00PM by Spinner Staff
Filed under: The Hit List

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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 dream.


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 heartbreaker 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.


9.'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.


8.'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.


7.'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.


6.'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.


5.'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.


4.'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").


3.'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.


2.'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.


1.'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

Cool list for once.

I subscribe to the pernice brothers mailing list, and they sent a link to this list when it appeared with Chicken Wire ranked #1. I absolutely love every bloody thing Joe Pernice has made, whether he records solo, as Scud Mountain Boys, Pernice Brothers or Chappaquiddick Skyline. I think he's incapable of recording a song I don't like, and Chicken Wire is one of his finest.

mimi07 said:

These are great choices! I'm shocked Lou Reed's "Sad Song" doesn't make the cut, though. That's what I would have pegged for number 1.

A pretty good and unique list overall, I think, though The George Jones track probably deserved to be ranked #1. The only real quibble I have is that I find Jeff Buckley to be far too vocally hysterical for my tastes, but I know lots of people love him and regard his album as a classic.

Moonbeam said:

I love that song and the album, but I don't find it the least bit sad - if anything, i think it's quite silly
with the grandiose lyrics, bombastic music, over the rainbow quote and all that stuff...

damosuzuki said:

In the context of that album, the song is really aptly named for me. Those woodwinds get me every time.

i love love LOVE 'gloomy sunday'.

i have so many favorite versions of that song: billie, sinead, diamanda...

Anxiety said:

bjork?

Love the list...here's my 25 or so

Sad Eyes - Robert John
"Sad eyes, turn the other way, I don't wanna see, you cry"

Everybody Hurts - R.E.M.

Two Out of Three Ain't Bad - Meatloaf
"I want you, I need you, but there ain't no way I'm ever gonna
love you...now don't be sad, cause two out of three ain't bad"

The Dance - Garth Brooks
"He could have missed the pain, but he'd have had to miss the dance"

Read 'em and Weep - Barry Manilow
"It's there in my eyes, can't you see me tonight, come on and look at
me and read 'em and weep"

Ain't No Sunshine When She's Gone - Bill Withers
"This house just ain't no home, anytime she goes away"

She's Not Cryin' Anymore - Billy Ray Cyrus
"She ain't lonely any longer, there's a smile upon her face, a new love
takes his place, she's not cryin' anymore"

A Total Eclipse of the Heart - Bonnie Tyler
"Turn around bright eyes...every now and then I fall apart, and i need
you now tonight and i need you more than ever"

Rainy Days and Mondays - The Carpenters
"Hanging around, nothing to do but frown"

Water from the Moon - Celine Dion
"What do I gotta do? Do I gotta get water from the Moon to make you love me?"

When You Leave That Way, You Can Never Go Back - Confederate Railroad
"Train won't run on a torn up track...sometimes I wish I'd never roam"

Hello Darlin' - Conway Twitty
"Let me hold you in my arms for old time's sake"

Two Occasions - The Deele
"I only think of you on two occasions, that's day and night"

American Pie - Don McLean
"The day the music died"

Desparado - The Eagles
"Why don't you come to your senses, you've been out ridin' fences for so long now"

How To Save A Life - The Fray
"I'da stayed up with you all night, had i known how to save a life"

If Tomorrow Never Comes - Garth Brooks
"Will she know how much you loved her, if tomorrow never comes?"

She's Every Woman - Garth Brooks
"She'll rage just like a river, then she'll beg you to forgive her"
"She's every woman that I've ever had, and she's every woman that I've never had"

A Different Corner - George Michael
"To lose you would cut like a knife, so I don't dare"

Don't Cry - Guns N'Roses
"I know the things you wanted, they're not what you have...don't you cry tonight, cause i still love you baby"

Take Me Home Country Roads - John Denver
"Take me home, to the place I belong, West Virginia, Mountain Momma, take me home, country roads"

Open Arms - Journey
"Hoping you'll see, what your love means to me...open arms"

Through The Years - Kenny Rogers
"You've never let me down, you turned my life around...the sweetest days I found, i found with you"

Beth - Kiss
"Just a few more hours and I'll be right home to you...Beth what can I do?"

Still - Lionel Ritchie
"I wonder, If you need me now..."

All Cried Out - Lisa Lisa & Cult Jam
"All alone on a sunday morning, outside I see the rain is falling...inside I'm slowing dying, but the rain won't hide my crying"

Which Way Does That Old Pony Run - Lyle Lovett
"How much is that saddle and a straight shooting gun? Which way does that old
pony run?"

She's Out of My Life - Michael Jackson
"I don't know whether to laugh or cry, I don't know whether to live or die. It cuts like a knive, she's out of my life"

I Go Crazy - Paul Davis
"When I look in your eyes, I still go crazy, no my heart can't hide that feelin' inside"

One More Night - Phil Collins
"Gimme just one more night, cause i can't wait forever"

If I Could Turn Back The Hands of Time - R Kelly
"I did you wrong, I admit I did, and now I'm facing the rest of my life alone"

Right Here Waiting For You - Richard Marx
"Whereever you go, whatever you do, I will be right here waiting for you"

Almost Over You - Sheena Easton
"Your such a sly one with your cold cold heart"

Bridge Over Troubled Water - Simon & Garfunkel
"When your down and out and feeling small"

It Might Be You - Stephen Bishop
"It might be you I been waiting for all of my life"

Love Will Lead You Back - Taylor Dayne
"You'll walk out this door, but someday you'll walk back in"

Let Her Down Easy - TTD
"Even though there's nothing I can say, to cheat you and nature anyway, let her down easy "

Un-Break My Heart - Toni Braxton
"don't leave me in all this pain "

Nobody Knows - Tony Rich
"Like a clown I put on a show, but I'm dying inside and nobody knows it but me"

The Night The Lights Went Out in Georgia - Vicki Lawrence
"that's the night they hung an innocent man..."

Whenever You Come Around - Vince Gill
"Face of an angel, pretty eyes that shine...wishing you were mine"
[Edited 5/15/07 20:06pm]

I look at this list, and I wonder how they left out Toni Braxton (Another Sad Love Song, Breathe Again, Seven Whole Days, There's No Me Without You, Un-break My Heart) or Phyllis Hyman. Somehow, I feel like all of Phyllis Hyman's songs, while beautifully sung, made me want to slit my wrists.

728huey said:

Toni made my list!

I don't know if my list fits the title of this thread but I especially 'feel' these sad ones

1. While You Were Here - Eric Benet - ...The song is written to the mother of Benet's daughter. The mother - Benet's girlfriend - was killed in an auto accident.

2. Bitter - MeShell Ndegeocello - Brutally honest.

3. Truth Hurts - Usher - If want to hear a contemporary SOUL song listen to this Jam/Lewis production.

4. Faithful - MeShell Ndegeocello ...no one is faithful, I am weak, I'll go astray.

5. September 29, 1991 - Foley ...This is an instrumental Foley wrote the day Miles Davis passed away.

6. Do What I Gotta Do (and break your heart) - Ralph Tresvant.

7. Tangerine - Prince

8. How Deep is Your Love? - Keith Sweat ...You kiss me but it's not real

9. Crying Overtime - Alexander O'Neal

10. Lonely - Janet Jackson

11. The Life - Wendy & Lisa ...and it only gets harder.

12. The Beautiful Ones - Prince

13. Condition of the Heart - Prince

14. I Can't Get Over You - Gap Band

15. Nothing Compares 2 U - The Family

16. Push & Pull - Nikka Costa

17. Pain - Tony Toni Tone'

18. What Would it Take? - Tony Terry & Flame

19. Without You In My Life - Switch

20. Why Should I Cry for You? - Sting

21. Love TKO - Teddy Pendergrass

22. No Show - Kool & the Gang

23. Distant Lover - Marvin Gaye

24. Promises Can Break - The System

25. Until You're In My Arms Again - NPG
[Edited 5/19/07 22:42pm]

GangstaFam said:

i had no idea.

are there any other bjork covers i should know about? is there a bjorkified version of the dirty mind album floating around out there somewhere?

Tears In Heaven - Eric Clapton

Would you know my name
If I saw you in heaven
Will it be the same
If I saw you in heaven
I must be strong, and carry on
Cause I know I don't belong
Here in heaven

Would you hold my hand
If I saw you in heaven
Would you help me stand
If I saw you in heaven
I'll find my way, through night and day
Cause I know I just can't stay
Here in heaven

Time can bring you down
Time can bend your knee
Time can break your heart
Have you begging please
Begging please

(instrumental)

Beyond the door
There's peace I'm sure.
And I know there'll be no more...
Tears in heaven

Would you know my name
If I saw you in heaven
Will it be the same
If I saw you in heaven
I must be strong, and carry on
Cause I know I don't belong
Here in heaven

Cause I know I don't belong
Here in heaven

I like many of these choices. I'd recommend, in no order:


"Lush Life" -- John Coltrane and Johnny Hartman

"And God Created Woman" -- Prince and the New Power Generation

"Sincerity" -- Me'Shell Ndegeocello

"What A Fool Believes" -- The Doobie Brothers (a deceptively sad tune)

"Deacon Blues" -- Steely Dan

"Everything's All Right" -- Jesus Christ Superstar (orig. Broadway cast), a lullaby sung by Mary Magdelene to Jesus days before His Crucifixion

"Old Friends 4 Sale" -- Prince and the Revolution

"All Blues" -- Miles Davis

"Learnin' The Blues" -- Louis Armstromng and Ella Fitzgerald

"Passion" -- Peter Gabriel

"Mercury Falling" -- Sting

"Lonesome Tears" -- Beck

"time" -- Musiq

"My Life" -- Mary J. Blige

"Green Eyes" -- Erykah Badu

"Can't Explain" -- Jill Scott

"Can't We Be Friends?" -- Frank Sinatra

"Otha Fish" -- The Pharcyde

"I Can't Make You Love Me" -- Bonnie Raitt
[Edited 5/16/07 11:46am]

these two are my top picks:

Love Tried To Welcome Me(this song gets me EVERY TIME i hear it. )
This Used To be My Playground

Artist:Madonna
[Edited 5/16/07 11:44am]

"Failure" - Swans
"Spiritual" - Johnny Cash
"Black Boys on Mopeds" - Sinead O'Connor
"Cold" - Annie Lennox
"Crowds" - Bauhaus
"Untitled" (from the "Disentegration" album) - The Cure
"My World Is Empty Without You" - the Diamanda Galas version is my favorite (of course)
Just about anything by Tammy Wynette


sheesh, can ya tell i'm a reformed goth?

Anxiety said:

good ones.

Anxiety said:

Do you like Meredith Monk? Petula Clark? Burt Bacharach?

If so, I've got some goodies for you.

I think "I can't live without you" which was remade by Mariah Carey in the 90's (sorry can't think of who did the original) has got to be the most sad song ever. Truly depressing. Was it someone named Nilson who did it originally?

GangstaFam said:

i like all that stuff. not passionately, but yeah. all that's good.

I was thinking of "I know it's over" when I clicked on this thread.

Surprised something from Joni Mitchells Blue wasn't there "Little Green", or "Blue" or "The Last Time I Saw Richard" are all killers

early in the morning - gap band

john lennon's "beautiful boy" always made me cry
right around the line "i cant wait to see you come of age"

Michael Jackson

She's out of my life AND Gone to soon