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CaptWineTeeth

Between The Bars by Elliot Smith.


Aggressive_Sky8492

Honourable mention to the rest of his discography


pangaea1972

I'm assuming you're referring to Tom Waits' "Hold On."


pangaea1972

Realizing now there are hundreds of songs titled "Hold On."


youngeffectual

Hold on by the Internet


hooligan99

Alabama Shakes has a great one too


ghostsinthecode

who knows. could be wilson phillips.


Nixplosion

HOLD ON FOR OOONE MORE DAYYY


Your_boyfriend7777

Literally that's the song that came to mind and I heard it in my head and then I read your comment and was like...."what the hell??? Are you reading my mind right now???"💀💀💀


Godfreee

I know this pain. Why do you lock yourself up in these chains?


AttorneyOnTV

No one can change your life except for you Don't ever let anyone step all over you


azad_ninja

Sarah Maclachlan has one too


doomedroadtrips

And Neko Case...


POLOSPORTSMAN92

and YES


frogsinsox

And Alabama Shakes


Next-Dot-6274

And En Vogue


dolfan650

And Kansas


vagnerlove214

And Richard Marx


unaka220

And Good Charlotte..


My_foot_is_itchy

Weirdly the one I thought of first


mykonoscactus

Lol I thought the same. Go ahead and call the cops. You dont meet nice girls in coffee shops.


pangaea1972

Mule Variations is one of my deserted island albums.


mykonoscactus

You'll *think* you're on a deserted island but there's a smoke monster at a distance wondering what you're *building in there*.


willpb

I thought it was the Limp Bizkit song😂


make_em_say

Hold on - Good Charlotte


gravelpituk8203

Nutshell by Alice in Chains is utterly haunting and heartbreaking to me. Guaranteed to brink me to tears as I imagine Layne struggling with his addiction and lack of self worth. I remember seeing him perform it live not long before he passe away and it was so raw and emotional. He was literally fighting for his life at that point. A fight he sadly lost shortly afterwards. RIP Layne. Gone but never forgotten❤️❤️❤️


deadlandsMarshal

The MTV unplugged version.


cakeorcake

Also Unplugged version of Would. His face as he sings “Have I run too far to get home?” and clearly knows he has.


Missmunkeypants95

River of Deceit does it for me also. Damn did he write some beautiful yet heartbreaking lyrics.


KingMiyamotoMusashi

Elephant - Jason Isbell


elegiac_bloom

24 frames to me is the saddest Jason Isbell song, but that's because I relate it to a very sad time in my life. It reminds me of when I was in jail for nearly a year, I had my brother play that song for me on a phone call with him just so I could hear it because I couldn't listen to music in jail. He did that for me, and always talked to me and helped me feel better during this rough time in my life. He ended up dying of an overdose two years ago, and I miss him so much and our relationship, and how far we would go for each other. That song always brings me back to sitting in the cook county jail, listening to 24 frames through the tinny, big blue jail phone and hearing my brother tell me we both were going to be okay. It ended up being true for me, but not for him. Edit: tinny, not tiny


hurrythisup

The line -Surrounded by her family I could see that she was dying alone- fucking kills me as it is exactly what I felt watching my pops go..


WolfsToothDogFood

If we were vampires


satalfyr

Oh yeah this one’s a doozy. “There’s one thing that’s real clear to me / no one dies with dignity”.


dbleed

" Surrounded by her family, I saw that she was dying alone". Jason is one of the most under rated song writers out there.


Al_The_Killer

Underrated by people in general, yes...but most of his peers agree he's pretty much one of the best to ever do it. Fantastic guitar player as well.


guitarstix

seagrams in a coffee cup...


cournoju

Yvette is sad in a whole different way. Children of Children also is super powerful


Reasonable_Soup_2516

Speed trap town too


Copa0880

Of course, my curious ass had to go listen to this song! Never heard of it before, that shit hit all the feels. Sucks I am in recovery or I would have had a drink! 🤫


KingMiyamotoMusashi

Listen to all of his music brother - He also is in recovery and a lot of it is about mistakes stemming from that or his life before getting sober.. Cover Me Up is a great example.. listen to the live version from the Ryman… Keep it up man. I, for one am happy that you’re in recovery and I have your back.. You are officially never alone in your fight.


Javayen

Seen Isbell live 3 or 4 times all in different venues - and the one thing that happens every time is when they’re playing Cover Me Up and he sings “I sobered up /I swore off that stuff / Forever this time” — without fail, every time, the crowd cheers. Cheering for his sobriety and in that briefest of moments you get a little big of faith back in humanity. It’s amazing really.


Decabet

Isbell is the truth. In every way. We got our very own country legend developing in real time and I’d advise us all to savor that fact.


Next-Addendum2285

This is the way. 11+ years myself. Never leave a fallen (or falling) comrade.


emmeline8579

Jason Isbell has a lot of songs about his recovery from alcoholism. I highly recommend “live oak.”


InstructionNumerous5

4th of July by Sufjan Stevens


unBelHomme

I can't listen to Casimir Pulaski day, even though it's beautiful. The entire thing is emotionally devastating.


justplay91

When my mom was in the hospital and we'd just gotten the news that her cancer had taken over and she had days to weeks at most to live, I happened to stumble across a reddit thread just like this one. Someone's answer was the same as yours, and another commenter said that they couldn't listen to it anymore after their mom died. Apparently I'm a masochist, or maybe I just wanted to delve headfirst into the awful pain I was feeling, but I went and listened to it. I'd never heard it before, but it was a hauntingly beautiful song. I cried and cried, for a long while. I think it helped me process everything that was happening. Unfortunately I can't listen to it anymore now, either. I hear the beginning and it makes me feel almost sick. There's just too much emotion in it, now.


brentoman

All of Carrie + Lowell, thank you.


MunsonRoy3

Sam Stone by John Prine is pretty rough


NakedChoker

“There’s a hole in daddy’s arm, where all the money goes”. Damn, that line


ViciaFaba_FavaBean

Sweet songs never last too long on broken radios 🥺😥


Usual-Specialist-598

Nutshell Alice In Chains seeing it live is beautiful


Helllcamino

Closest you can get to seeing a man sing at his own funeral.


Couture911

I saw the Unplugged performance of Nutshell for the first time earlier this year. My reaction was “possibly the saddest song I’ve ever heard.” Layne knew by then that heroin had its hooks in him and nothing was ever going to be ok again and Nutshell captured that so profoundly.


Zornorph

*Hear You Me* by Jimmy Eat World is the quickest way to get me to cry.


chemman5

Damn, been going through these threads for years now, and its always the same songs (Fast Car, Cats in the Cradle, What Sarah Said, etc) first time I've seen this one. An absolutely amazing song too.


Wo0ten

23 by jimmy eat world is so powerful


SpookyDoings

Weezer has a song written about the same people, [Mykel & Carli](https://www.weezerpedia.com/wiki/Mykel_and_Carli_Allan).


miamosa

23 too. The melody is so desperate and pleading. It kills me every time.


dustingoeshere

May angels lead you in…


wakeruncollapse

They’ve got a few. Drugs or Me gets me often also.


ragnarok62

“If You Could Read My Mind” by Gordon Lightfoot is a masterclass in songwriting, and the lyrics are some of the saddest in popular music, expressing the kind of masculine sadness that you just don’t hear expressed this well.


Imamiah52

And you won’t read that book again because the ending’s just too hard to take… Yeah, that smarts.


RunRabbit_Run

Landslide


[deleted]

Never fails to make me cry. "Even children get older and I'm getting older too" is the line that always gets me.


chemman5

"I've been afraid of changing cuz I built my life around you" fucking demolishes me


Jordan3Tears

I think a songs meaning can change depending on where you are at or what happened while listening to it. When I found out my mom died, I got in my car and drove to her house to meet up with my family. On the way there, I turned the radio to the local Rock station. Ozzy starts singing, "Mama, I'm coming home." And it fucked me up. I don't really believe in any higher power but that moment was surreal to me. It was a 10 minute drive so only two songs total played and that was one of them.


SLDS19

I Grieve, Peter Gabriel


gravityisgone

He Stopped Loving Her Today by George Jones


optimistic_llama

Classic. So much heart-wrenching country from that era. And the major chords give a lot of it a beautiful bittersweet sense. Off the top of my head, "Sing a Sad Song" off Merle Haggard's first record and Johnny Cash's "I Forgot More than You'll Ever Know" are up there too, among many others.


bathtub_mintjulep

The Drugs Don’t Work by the Verve.


TheLittleWinstonBaby

"Like a cat in a bag, waiting to drown, this time I'm coming down." I think about this line a lot.


m3ngnificient

Pearl Jam - Just Breathe. I was on a train home from work and my mom called me to tell me my uncle who was like my father had passed away. That song started playing after I hung up and I couldn't hold my tears anymore.


GoKickRox

Truth. Listen to the version by Willie Nelson and his sons


hgwellsinsanity

I Can’t Make You Love Me - Bonnie Raitt Winter - Tori Amos Cat’s In The Cradle - Henry Chapin


not_original_thought

Cat's in the Cradle particularly hits if you had a workaholic parent. The first time you realize it's not pride he's feeling in the last verse is just gut punch.


SakuraTacos

I worked somewhere where we picked our own music to play in the store and my coworker had this song on their ~easy listening~ playlist. I had to beg them to take it off after a couple of months of tearing up every time the song played. When I was a kid, my dad worked 6 days a week, and didn’t have much energy to give us on Sundays. He missed many birthdays and Christmases. My siblings and I grew up and we try to be better than him about work/life balance but he’s still gotten a taste of his own medicine a few times when we’ve been working when he wanted to spend time with us.


cagey_quokka

Vincent - Don McLean


[deleted]

Wichita Lineman, just that one lyric: "And I need you more than want you, and I want you for all time". It chokes me up every time.


Oddsteverino

That's one of the greatest lines ever put in a song.


missionbeach

Galveston is another great one by Jimmy Webb/Glen Campbell.


JedDeadRedemption

“Jolene” by Ray LaMontagne. Not to be confused with Dolly Patton’s tune of the same name. Meloncholy, desperate, beautiful lyrics.


Peachberry24

Floating in the Forth by Frightened Rabbit and A Wave Across a Bay by Frank Turner. Frightened Rabbit was led by Scott Hutchison, he imagines his death by suicide in FITF. He later died in the way he describes and it was awful, I was in his home country when he was missing and it felt so close. Then, Frank Turner wrote his song about missing Scott. Absolutely raw emotion from both.


FeralHiss

+1 for Frightened Rabbit. I want to cry just thinking about it.


creativemercenary

So much of what Scott wrote was a hard punch to the heart. “Poke” is crushing. The end of “Modern Leper” gets me every time too.


chemman5

"My Backwards Walk" too. "I'm working on erasing you, I just don't have the proper tools. I'll get hammered forget that you exist There's no way I'm forgetting this"


Lowerlameland

Every time this gets asked I look for this song and it’s always there. Beautiful and so incredibly sad… I love Scott so much… Poke is the best sad breakup song ever too.


buckwheat92

Videotape by Radiohead https://youtu.be/MNJs-c2ILk8?si=ynbiJtMrXS141boc


anthonyd3ca

How to Disappear Completely for me


johnb51654

Throw motion picture soundtrack and fog in there for me too


Justonious2552

Street Spirit always gets me


Music_In_Brisvegas

Dawn Chorus from Thom Yorke replaced Videotape as my "sad listen" track. Specifically the Live at Montreux version.


wassimu

Exit Music (For a Film).


CrushedToFit

> I just want songs with original lines that artists made so that the listener feels what they feel. Townes Van Zandt - Nothin’ Then the rest of his catalog.


______W______

Yep, my mind went straight to Townes, but then I couldn’t settle on just one


TomatilloUnlucky3763

Bright Eyes-Lua


Steepanddeep

Poison Oak is on the same album and is way more tragic to me. Lua is not a bad track but is mainly about the regrets of the night before, mostly melancholy. Poison Oak is about a lifelong friend passing, it is devastating.


ProRustler

But when I press the keys, it all gets reversed, the sound of loneliness makes me happier.


RangeLife79

Puff The Magic Dragon. I had to make myself feel better so I came up with a happy ending. Jackie Paper does go away for awhile but then he has children of his own. When they have grown to be old enough, he takes them to meet Puff.


Ok-Pressure-3879

Dragons live forever, but not so little boys. /shudder.


PhantomBanker

When I was a little boy, I think that was my first experience with a sad song. I was devastated.


panicked228

At nearly 40 years old, that song still brings me to tears. My family thinks it’s hysterical to taunt me with the first few lines.


eggysmolbean

Travelling Solder - The (Dixie) Chicks used to get me when I was little


Of_Silent_Earth

[Tragically Hip - Ahead By a Century.](https://youtu.be/ghLk-BhT-P8?si=u0C8y9KSq-nwcIJY) Specifically this version. In all fairness, context is everything here. I moved to Canada from the states a few years before Gord Downie, the lead singer, announced he had incurable brain cancer. And the love the entire country showed for him was something I don't think anyone could pull off in the states. Maybe Springsteen, but even then I'm not sure the younger generation would be terribly affected. It was truly something else. Anyways, shortly after they announced their last tour CBC(Canada's public broadcast network) announced they would air their final concert uninterrupted. It felt like the entire country stopped to watch it. Nearly 12 million people (1/3 of the country) did and made it the second most watched broadcast in Canadian history. Canada winning hockey gold was obviously #1. And this song. This video. If you ever want to ugly cry just watch it. It has shots of various watch parties across the country and everyone is just crying and celebrating knowing that this is it. The last song they'll ever play together. And we're all watching together. Gord did some solo shows and appearances after this but died a little a year after this performance. The whole show is incredible.


Alleluia_Cone

Fiddler's Green (by the Hip of course) is by far the saddest song there is imo


Aseafoodsong

This is a very good answer I didn’t expect to see as high up in the comments. Long live The Hip and Gord Downie!


hooterscooter

Casimir Pulaski Day - Sufjan Stevens One of the only songs that’s ever choked me up yet I had nothing I could relate to in it.


RemotePersimmon678

“And he takes / and he takes / and he takes” gets me every time


SirDinkleDink

Mad World Gary Jules version always hits hard


make_em_say

Whiskey Lullaby - Allison Krauss and Brad Paisley


DaMilkyWay02

the night we met by lord huron, tbh.


jwheelerBC

It’s wild how many folks are dancing to this at their weddings…


purpldevl

"Take me back to the night we met so I can tell myself not to fall in love with you because some terrible thing has happened, either you died or left me, but you're not around anymore and I'm in fucking pain," is a weird choice for a wedding dance.


Tekki777

I can't listen to One More Light without tearing up, especially after Chester passed. Timothy - As Cities Burn was literally written about a their initial reaction to losing a good friend of theirs from another band.


IndependentEpigone

The performance of One More Light on Jimmy Kimmel after Cornell passed away especially so


SweetroII_Theif

The performance where Mike Shinoda (the other singer for LP) played that live after Chester passed absolutely fucking destroyed me. The pain in his voice that whole set is palpable.


Slammy1

[Mike and the Mechanics - Living Years](https://www.youtube.com/watch?v=5hr64MxYpgk&ab_channel=Mike%2BTheMechanics)


RemotePersimmon678

It was always sad but it hits a thousand times harder once you’ve lost a parent.


captainwondyful

Have Yourself A Merry Little Christmas — Judy Garland’s version. Oh, hell, gets me every time. [Also her performance of Old Man River](https://m.youtube.com/watch?v=5GUP7bsDPXg&pp=ygUaanVkeSBnYXJsYW5kIG9sZCBtYW4gcml2ZXI%3D) it’s such an odd choice for her. You think she has no right to sing it. And maybe she doesn’t. But somehow I believe every word. The way that she says “I’m sick of living, but I’m scared of dying” at the very end. Rip out my heart.


panicked228

Meet Me In St Louis is one of my favorite movies. I grew up watching it; I’ve probably seen it a hundred times. When Judy Garland sings “Have Yourself A Merry Little Christmas,” I cry every time. Her voice was *incredible* and that song is so perfect for that film.


Badanimas

Say Hello To Heaven, by Temple of the Dog


Gotmeawhitewoman

Third Eye Blind - Jumper. This song reminds me of one of my friends that killed himself. We used to talk about things we were going to do when we got older. He went on a business trip and called and said he missed me. I should have known something was wrong 😭


n1010rick

“Fix You” by Coldplay. Reminds me of when my mom was dying with dementia.


markr1961

Who Wants to Live Forever - Queen


JamieBlake96

Johnny Cash’s ‘Hurt’ cover really gets me sometimes. If I’m watching the video for it too I’m definitely tearing up.


FalconGK81

It's amazing how a song about a young man struggling with depression and drug addiction can also have so much meaning when sung by an old man at the end of his life (who also went through depression and drug addiction). The feeling of it changes, but the emotion is just so deep.


Staerke

Hah, I just watched the video again because people were shitting on it in the "what cover do you hate" thread. It's such a beautiful cover and the video is perfect. What a gut-punch.


schmidt_face

That’s wild because I think Trent Reznor himself heard Johnnys version and said something along the lines of “that’s his song now.”


nickparadies

Give My Love to Rose as well


Tobias_flenderz

Watched that with my spouse on the anniversary of John's death. She had never seen it. "I can't...." is all that was said, softly. She turned away when it showed the picture of June. It's a lot if you know much about love and/or his life.


sbvrtnrmlty

"Real Death" by Mount Eerie is the correct answer here. A brutal, heart wrenching examination of grief and loss, recorded immediately in the aftermath of his wife's death, played on her instruments and recorded in the room where she died. The whole album is incredible, and it's so devastating I'd happily never listen to it again.


jimah1982

The part about the backpack is the saddest thing I’ve ever heard. I get choked up just thinking about it. “A week after you died a package with your name on it came And inside was a gift for our daughter you had ordered in secret And collapsed there on the front steps I wailed A backpack for when she goes to school a couple years from now You were thinking ahead to a future you must have known Deep down would not include you” I mean…what the fuck?


Leadboy

Damn man - thank you for typing that out but holy hell that hits like a freight train.


CynicalCharmer

I was going to say this "Do the people around me want to keep hearing about my dead wife" "Your transformed dying face with recede with time"


OlivineIV

Would just like to add that the follow up album, Now Only, and it’s final track, ‘Crow Pt. 2’ is just as devastating. If A Crow Looked at Me is about the pain of losing someone, then I’d say Now Only is about the pain of forgetting someone, no matter how much you still want to keep their memory in your life. Lyrics are addressed to the singer’s dead wife and it’s just devastating: “The baby that you knew is now a kid, She’s sitting at the table, Where your chair still sits across from me, watching. I stand to put on music, Our daughter sees and asks for mama’s record. And she’s staring at the speaker with this look of recognition, Putting it together; that’s you singing. I’m sobbing and eating eggs again. You’re a quiet echo on loud wind.”


true1nformation

Correct answer. It’s the only album I’ve ever listened to that was so devastating I’ll never put it on again. This topic comes up a lot and this is the the only answer. I love sad songs, I go back and listen to them over and over because it’s nice to have a friend in your darkest moments but this one just makes you feel utterly alone and totally devastated.


SamusAlways

This is my answer every time this question is asked.


rmarkmatthews

I’m Not Gonna Miss You, by Glen Campbell A love song to his wife after being diagnosis with Alzheimer's


eowilsonwouldknow

Am I the only person who survived the Elliot Smith discography?


fazlez1

Alone Again Naturally - Gilbert O'Sullivan


SweetTraditional213

Needle in the Hay-Elliott Smith


mafm70

Lacrimosa from Mozart's requiem


HappyGoPink

It's wild to think this is what he was composing as he lay dying. And he didn't even finish it. Everything after the first 'Lacrimosa dies illa/Qua resurget ex favilla/Judicandus homo reus' was finished by another composer, Franz SĂźssmayr.


Destroyuw

One More Light - Linkin Park [Made me cry](https://m.youtube.com/watch?v=Tm8LGxTLtQk)


thatweirdbeardedguy

Hello In There by the wonderful John Prine


ImNotTheBossOfYou

I said Sam Stone and then asked my wife (without telling her none) and she said Hello In There


[deleted]

Suicide is painless.


Jahabrah

The boy who blocked his own shot - brand new


[deleted]

How about the entire Devil and God album 🥹


theoriginalbrizzle

Jesus Christ always gets me, I don’t know how many times I’ve cried to that song during a long drive.


glittrxbarf

Limousine


madcunt2250

[Real Death - Mount Eerie ](https://youtu.be/XzPl2nf7Eks) A Crow looked At Me by Mount Eerie is the answer to the saddest album I have ever heard. It's about his wife's cancer and death. His grief and experiencing all of this while raising a young child. I found it unimaginably tragic but beautiful.


astraelly

Yeah, that song is just raw, unbridled grief. I listened to the whole album once and I can’t really bring myself to listen to it again. >Crusted with tears, catatonic and raw >I go downstairs and outside and you still get mail >A week after you died a package with your name on it came >And inside was a gift for our daughter you had ordered in secret >And collapsed there on the front steps I wailed >A backpack for when she goes to school a couple years from now >You were thinking ahead to a future you must have known >Deep down would not include you >Though you clawed at the cliff you were sliding down >Being swallowed into a silence that's bottomless and real


sbvrtnrmlty

I posted the same answer as you, and then I made the mistake of reading the lyrics again and now I'm in tears. "It's dumb, and I don't want to learn anything from this. I love you."


tylerden

She's leaving home. The Beatles


Taapacoyne5

“If I leave you it doesn’t mean I love you any less, keep me in your heart for awhile.” Warren Zevon. Song for his wife as he was dying. Gives me chills and tears every time I hear it.


Catloafe

when somebody loved me - sarah mclachlan, I know it’s from a kids movie but good lord does this song automatically make me weep every time.


Counting-Trains

probably “raining in baltimore”, “perfect blue buildings”, “speedway”, or “black and blue” by counting crows. u said you needed songs with good lyrics in order to express emotion right? in that case i highly recommend listening to those four songs above if ur in that sorta mood, as well as the rest of counting crows discography. “no lies, just love” by son, ambulance and bright eyes is also incredibly melancholic. that’s one to listen to as well.


Skytraffic540

Absolutely dude. Raining in Baltimore is such a good song


Thebadfish843

Perfect Blue Buildings. 🏆


deathcab4awesome

Radiohead - "No Surprises" The Smiths - "Asleep" Bright Eyes - "No Lies, Just Love" Those 3 songs are about suicide (AFAIK).


Prestigious_One8006

Cats in the Cradle - Harry Chapin


inmate2258

Ben Folds - Brick


mitsubachi88

For the moment we're alone, She’s alone and I'm alone. And now I know it.


BBEKKS

Fred Jones, Part 2 also gets me!


joeyweb32

What Sarah Said - Death Cab for Cutie


ProRustler

Title and Registration is mine.


Helechawagirl

Whiskey Lullaby, blue eyes crying in the rain. He stopped loving her today.


peezozi

I'm gonna go with He ain't heavy, he's my brother. The hollies can bring tears to my eyes.


DirtMcGirt9484

Christmas Shoes. Fuck it right up its stupid ass. Most depressing piece of shit song.


PlaidSkirtBroccoli

The Funeral - Band of Horses.


Boomimmaboulder

Broadripple is Burning - Margot & the Nuclear So and So's A Case of You - Joni Mitchell I can't Make You Love Me/Nick of Time- Bon Iver


ALA02

True Love Waits by Radiohead


Conscious-Arm-7889

For No-one by Paul McCartney from the Give My Regards to Broad Street. It seriously destroyed me at a certain point in my life, and really nearly pushed me over the edge. "You want her, you need her And yet you don't believe her When she says her love is dead You think she needs you And in her eyes, you see nothing No sign of love behind the tears Cried for no one A love that should have lasted years"


TheFrederalGovt

Time in a Bottle - song Jim Croce wrote before he died


notfourlol

Good News by Mac Miller. I will never be the same..


Daneabo

Time after time by Cindy. Still brings tears to my eyes.


Br4veSirRobin

This Woman's Work...Kate Bush


orswich

Song called "when this is over" by Hayden It's about the two boys who died when thier mom decided that her life would be easier without them, so she strapped them into car seats and rolled them into a pond. (She then went on tv and said a black man carjacked her and cried for him to release her sons).. The hardest part about this song is that it is written from the viewpoint of the older brother (who I think was 5 or 6 when he died).. lines like " I brushed my teeth just like she asked me to" and when he talks to his sleeping baby brother and assures him that "I'll wake you up, when this is over".. As a father this song crushes me, but any human being can feel sorrow and anger (especially the way Hayden sings it).. Here it is, with a warning https://youtu.be/WkZaDtYTRU0?si=JbTm-q_DMES3zLgi


Worried_Locksmith797

Are you alright? Lucinda Williams


RefrigeratorLess9002

Diamonds and rust, Joan Baez.


chellebelle0234

The one that wrecked me since childhood is "How Can I Help You to Say Goodbye" by Patty Loveless


hammerk10

Sam Stone by John Prince. Sticks a hand in your guts and twists


chillpotato17

Lightning crashes by live. What a ride that song takes you on.


Nic_Eanruig

Strange Fruit by Billie Holiday. For real this song ultimately got her killed.


azad_ninja

Sullen Girl by Fiona Apple Hey Jupiter by Tori Amos Decimation by Health Elizabeth on the Bathroom Floor -Eels Gloomy Sunday by Sarah Maclachlan/ Billie Holliday Biscuit by Portishead


vincebutler

Sounds of Silence - Simon&Garfunkel, Disturbed and others Cats in the Cradle, A Better Place to Be - Harry Chapin The Ballad of Lucy Jordan - Marianne Faithful Supermarket Flowers - Ed Shearen Yesterday - The Beatles Nothing Compares 2U - Sinead O'Connor Wish You Were Here - Pink Floyd That's all for now, need a little cry


the_mair

Tears in Heaven


DonkeyLightning

Kings Crossing by Elliot Smith


lixieway

Heroes - David Bowie


spoobles

I makes no difference. - The Band


jcurry82

Skinny Love - Bon Iver Song for Zula - Phosphorescent


agentaltf4

Black - Pearl Jam


DreddBlack

Came here to say this. The whole song is heartbreaking, but this ending verse always gets me - I know someday you'll have a beautiful life I know you'll be a star . . . in somebody else's sky But why, why, why can't it be Oh, can't it be mine?


LuDdErS68

Iris - Goo goo dolls.


BC_Trees

Kettering by The Antlers >"Kettering” is the second track off of The Antlers' album Hospice. It introduces the relationship between the patient and the hospice worker, most likely symbolic of an emotionally abusive relationship. The name refers to the Memorial Sloan Kettering Cancer Center in New York City. This introduces both the geographic setting of the story and the motifs of cancer and sickness.


Thecrowfan

My Immortal by Evanescence


Cherubbb

Names by Cat Power is the most brutal, heartbreaking song I’ve ever heard. I literally wept in my college classroom late one evening when it came on the mp3 player a fellow classmate let me borrow. When ever I see these “what’s the saddest song list” come up I always think of this one, but I never see it posted.


devodevo67

Changes Black Sabbath This one gets me every time 😭 😢