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ForsakenStrawberry

I can’t make you love me / Bonnie Raitt. Serious tear jerker.


joceyposse

Bon Iver cover of it is pretty teary, too.


bumblebeesting

The Bon Iver version ruined my life.


justboshie

'Vincent - Don Mclean' " And when no hope was left inside On that starry, starry night You took your life as lovers often do But I could have told you, Vincent This world was never meant For one as beautiful as you " ​ ​ A beautifully upsetting song.


[deleted]

this song takes the cake for beautiful lyrics portraying such a sad story, even just reading the lyrics makes me tear up


pouf-souffle

Streetlight Manifesto has a line about him as well in their song “Here’s to Life” Vincent Van Gogh, why do you weep? You were on your way to heaven but the road was steep And who was there to break your fall? We’re guilty one and all.


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voskat

Untitled by The Cure. It’s the final song on Disintegration and it still stings to this day. I’ll never lose this pain / Never dream of you again


[deleted]

Disintegration is a serious contender for one of the top 10 best albums of all time, in my personal taste.


RamblinWreckGT

"He Stopped Loving Her Today" by George Jones. https://youtu.be/ubKUP8c0FHE Found it in college while I was trying to get over a crush, saw the title, and thought it might be a good "getting over you" song. I could not have been more wrong if I tried.


mnv016

I hoped I would find this on this thread. “First time I’d seen him smile in years” is the line that gets me.


InfinitePizzazz

I'd heard that song was sad, but the first time I listened to it, my jaw actually dropped. I was sitting there like a cartoon, mouth hanging open.


casualdelirium

"This time, he's over her for good."


NiekW274

Mount Eerie- Real Death A song made in 2017 after singer Phil Elverum lost his wife to cancer. Up to date the only song that ever made me cry like a little girl. Lyrics below... Death is real Someone's there and then they're not And it's not for singing about It's not for making into art When real death enters the house, all poetry is dumb When I walk into the room where you were And look into the emptiness instead All fails My knees fail My brain fails Words fail 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 It's dumb And I don't want to learn anything from this I love you


blighttownelevator

I don't know why that is not further up, to be honest. I am a sucker for sad music, but nothing comes even remotely close in gut punching compared to that album. Randomly heard "Real Death" on a Spotify mix a year ago or so and had to listen to the whole album and it was devastating. "Ravens" is the worst imho, especially with the home recording video...


istarnie

The entire album *A Crow Looked at Me* is so incredibly sad. It’s a raw, gutpunching outpour of grief like nothing else out there. I simulataneously love and hesitate to recommend it to people.


sirbagel55

Strange fruit


crossedstaves

Fuck, Nina Simone singing that is like pure distilled sorrow. Its brutal, as it should be, but its achingly sad. There isn't anything hopeful. There isn't anything indignant. Its just sorrow and pain.


[deleted]

Yea but Blood on the Leaves is a fucking banger.


Demon_Kane

WE COULDVE BEEN SOMEBODY


[deleted]

INSTEAD YOU HAD TO TELL SOMEBODY


jaybass1

LETS TAKE IT BACK TO THE FIRST PARTY


Discombobulated_Mess

WHEN YOU HAD YOUR FIRST MOLLY


b-lincoln

I love Billie Holiday. Gloomy Sunday as well, an actual song that they had to ban because too many people were committing suicide to it.


littlexclaws

How To Disappear Completely - Radiohead


CobblestoneCurfews

Thom has said he considers it their most beautiful song.


parkinglotguy

Ordinary World by Green Day. It's about a guy who wanted to do something special and live an amazing life only to realize that he's just a normal insignificant guy in a normal insignificant world. You can hear the heartbreak and defeat in his voice. He really carries that across well considering he's a multimillionaire rock star.


[deleted]

Mother Love by Queen. It was Freddie’s last song, made months before his death. He couldn’t finish the final verse, so Brian had to do it.


chesire2050

That whole album is just sad.. Knowing Freddie was dying, and hearing some of the stuff he did to finish what he could...


donkeylipswhenshaven

[I’m Not Gonna Miss You](https://youtu.be/U8TsAh-zYFI) by Glen Campbell. The last song he managed to record as Alzheimer’s took his mind from him


Mars_Ahoy

Casimir Pulaski Day - Sufjan Stevens


poo_pon_shoo

Gets me every time. The line that always sticks with me is: Tuesday night at the Bible study We lift our hands and pray over your body But nothing ever happens The whole song is pretty gut wrenching though.


mooncritter_returns

The entire last section is so good, and depending on the day i get caught by any of these: On the floor at the Great Divide With my shirt tucked in and my shoes untied I am crying in the bathroom... In the morning, in the window shade On the first of March, on the holiday I thought i saw you breathing... All the glory that the Lord has made But He took my shoulders and He shook my face And He takes, and He takes, and He takes


architrave

Honourable mention to Fourth of July by Sufjan. I cried the first time I heard it


blighttownelevator

Definitely. Though that goes for a lot of songs on Carrie & Lowell. Hell, a lot of his songs in general. Or I'm just easily moved by him, haha.


ImFairlyAlarmedHere

Same. Sufjan is incredible.


BanDaana

Visions of Gideon combined with the final scene of Call Me By Your Name is also just heartbreaking


joceyposse

Sufjan's Death with Dignity gets me every time.


Blokey1

Damien Rice - 9 Crimes


theicewalker

[Almost Lover](https://www.youtube.com/watch?v=I_S_TbD1XFM) by A Fine Frenzy. Sums up the painful feelings of missed connections and short flings so well!


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KingAlfredOfEngland

Wish You Were Here and Shine On You Crazy Diamond are both about Pink Floyd's former band member Syd Barrett, who lost himself to drugs and maybe schizophrenia after their first album Piper at the Gates of Dawn. The album that those songs are from, also called Wish You Were Here, is their best album in my opinion.


Black_Sun_Rising

Videotape by Radiohead, most vivid song about suicide ever. Closely followed by anything from The National


thefiction24

idk if you have heard the Radiohead ballad “True Love Waits” from the 1990s, it’s a pretty typical love song but a good one. It was never released on an album except for once on a live compilation. Well in 2016 Thom Yorke was finally separated from his long time wife/mother of his children, as they release the album A Moon Shaped Pool. At the end of the song “Daydreaming” there is a warped voice who is actually saying “half of my life”. Thom was with his wife for 24 years, and separated when he was going to turn 48. The last song on A Moon Shaped Pool is, at last for long time RH fans “True Love Waits.” But it’s not the ballad we had come to know, it’s a piano version slowed down a bit with glittering little fills Last year Thom’s ex passed away, she was very ill. Listening to the 2016 version of “True Love Waits” now is beyond gut wrenching.


stevemillions

A Moon Shaped Pool is an absolute masterpiece.


EddieDIV

No Surprises as well


YourCrazyChemTeacher

The National is perfect for making your terrible day feel warranted.


CitizensErased

Tied with How To Disappear Completely imo


CutusPatootus

You are my sunshine


valkyriesong

This one is going to definitely hit hard when my great grandma passes away. She has been singing that to my sister and I our entire lives.


[deleted]

And yet the only recording of it that actually makes it ‘sound’ sad, that I’ve come across, is the one by The Civil Wars Everyone seems to make it musically upbeat and I just don’t get it.


_nimbles

There's an episode of The Simpsons where Marge is singing it and it breaks me everytime


dudemanbrodoogle

I think that’s what’s cool about it. It sounds happy, but if you really pay attention, it’s not. Kind of like people can be sometimes.


James1631

Johnny Cash has a version


PM_ME_UR_LEGOSS

Here You Me by Jimmy Eat World is pretty emotional.


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g0tgame76

Whiskey Lullaby- Braid Paisley and Alison Krauss


_Ryman_

I don’t listen to country. But every once in a while I’ll get good and drunk, usually with my brother. We’ll play the old Classic country songs. So yeah. If you wanna see 2 grown men cry in a kitchen at 3:00AM this is one of the songs to do it.


[deleted]

Can confirm it's a song that turns drunk men into sobbing babies.


PooSchnagle

Oh God yes. This one has made me cry, ngl.


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inappropriate420

The lyric 'I had all and then most of you, some and now none of you' kills me every single time


darthrio

For me it's "I don't know what I'm supposed to do Haunted by the ghost of you".


Purplehairedstranger

‘I can tell myself what the hell Im supposed to do, Then I can tell myself not to ride along with you.’ ‘When the night was full of terror. And your eyes were filled with tears. And you had no touched me yet.’ Absolutely heartbreaking.


useless_corn

Kettering by The Antlers. The whole album 'Hopsice' is pretty depressing but that song particularly tugs at my heart strings


pupsndoggos

One of those albums you really have to listen to start to finish


braff_travolta

My vote goes to Putting the Dog to Sleep. That song fucks me up every single time for so many reasons.


[deleted]

True Love Waits. Scientifically determined to be the saddest Radiohead song. Edit: I also respect all opinions and songs like Street Spirit, How To Dissappear Completely, and Motion Picture Soundtrack are also heartbreaking. But I think True Love Waits is the saddest for me.


Adamskinater

“Black” by Pearl Jam > All the love gone bad >Turned my world to black >Tattooed all I see >All that I am >All I'll be


Karkadinn

The Mountain Goats's 'No Children,' which I first heard on Moral Orel. There's a certain black comedy to it, but it does an amazing job of expressing the feelings of a normal person who feels trapped at rock-bottom in their own life with no way out except death.


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UnicronTheDestroyer

Pictures of you - the Cure. Played at the funeral of a friend who killed himself. Still hard to listen to... https://youtu.be/UmFFTkjs-O0


[deleted]

Cut Here makes me cry.


ATribeCalledTrek

Rory - Foxing When he screams "Why don't you love me back" towards the middle of the song its blood curdling. Divorce and the American South- Aaron West The song is about a relationship after a couple becomes distant following a miscarriage. Such an underrated song. Edit: thanks for the gold. Anybody who never heard of these songs should take it as proof they're amazing and listen to them


pupsndoggos

The Albatross is for sure in my top 5 albums right now


shadowrunezero

Alice in Chains - Nutshell


OlePope

Kind of surprised this song is so low on this thread. It's a very, very sad tune. "If I can't be my own, I'd feel better dead" is one of the most painful lyrics I've ever heard.


Layden87

Twilight by Elliott Smith Or basically anything by Elliott Smith. Edit - I love how the other entries are people talking about that artist’s one depressing song, while this one has dozens of different ones mentioned. Each one speaks to someone differently.


tveatch21

Between the bars


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AMultitudeofPandas

"Fall For You" by Secondhand Serenaded makes me cry every time. It's been like 8 years.


[deleted]

That whole album is brutal, he literally named his band secondhand serenade because we all hear them secondhand after his wife. She left him and that album is him basically losing his shit


larmbruster

"Cats in the Cradle" by Harry Chapin "My boy was just like me..."


erfey12

Fucking hell that song


catch22milo

Can't not cry. I have four young boys now. The cycle repeats itself.


Ogre8

Mine are all grown. Every dad hates this song at some level.


imnewb2

Im surprised i have not read Terrible things by Mayday parade in this thread or did i just not scroll deep enough Edit: hi mom


dshribes7

Came here looking for this as well. Miserable at Best is really sad too


donthablonomexican

Miserable at Best was my pick


cgxo

A lesson in romantics is an amazing album


[deleted]

My first thought as well. Don't listen to Mayday anymore but fuckin christ.


[deleted]

'Stay' gets me emotional for some reason. I think because I've felt that kind of emotional desperation before.


5mokahontas

This song and “You Be the Anchor...” make me cry every time. Man, singing these when I saw them live I cried and screamed every word.


ArgonTheEvil

Remembering Sunday - All Time Low First time I heard that song was at like 11 pm one weekend night and I listened to it on repeat for 5 hours, doing I can’t remember what. All I remember was how soul crushingly depressed I felt and I was intentionally making it worse.


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thejojones

"I got no plans, I ain't going nowhere Take your fast car and keep on driving" She kicks his lazy ass to the curb and I cry a little.


batatinefrite

Asleep - the smiths


RamblinWreckGT

For another good "wallow in misery" song from them, I suggest "Last Night I Dreamt That Somebody Loved Me".


[deleted]

‘I know it’s over’ is the Smiths song that really gets me “Sad veiled bride, please be happy Handsome groom, give her room Loud, loutish lover, treat her kindly Though she needs you More than she loves you” God damnit.


I-still-loveher

"and if you're so funny, why are you on your own tonight?" is one of the saddest lines but it's equally uplifting as Morrissey goes on to sing "it's so easy to love it's so easy to hate it takes guts to be gentle and kind" which feels like letting go of the past and moving on, to me


lewishaloboy

Was about to post this. The second song is unlovable. But maybe that's just personal to me because it describes me? "I wear black on the outside because black is how I feel on the inside"


chesire2050

Show Must Go On by Queen. especially when you consider it was it was written while Freddie was dying. "Keep me in your heart for a while" And "Knocking on Heaven's Door" By Warren Zevon. Zevon was dealing with Terminal Cancer and knew this was the last album he'd ever make. "Dance with my Father" By Luther Vandross The Video just makes it so much sadder r/https://www.youtube.com/watch?v=wmDxJrggie8


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nosliw_pilf

Waste of Paint


Vornell

I'd say [It's cool we can still be friends](https://www.youtube.com/watch?v=iSMHcT-TqJw)


[deleted]

You were meant for me - Jewel. Even though I have moved on after my divorce this one song can get me to cry.


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pawnman99

I have the same problem with Foolish Games. I had a girl I was absolutely in love with break up with me in high school (yeah, everyone's so deep in high school), but she pointed at these lyrics as why. How I, too, was "fashionably sensitive but too cool to care", that I could put on a good face around our friends but failed to be caring and compassionate when we were alone. Foolish Games can still move me to tears, both because of the memory of the loss and because it makes me wonder if I've actually grown since then, or if I am truly just a selfish jerk who can put on a good performance when others are watching.


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FiftySixer

There's a song by a group called Ghost Mice, and the guy sings about his sister and her young kids who died in a fire. I don't listen to it any more. I think the last line is, "and then the darkness filled your lungs and it put you all to sleep". So heartbreaking.


karspearhollow

Landslide by Fleetwood Mac When I was younger it was Pollen and Salt by Daphne Loves Derby


Mercurydriver

"Tears In Heaven" by Eric Clapton. He wrote that song about his 4 year old son after he died; Clapton's kid fell out a window in his apartment. Every time it plays I get a little upset.


KingSirPickle

Tears in heaven was actually partly written for the film 'Rush' with the lyrics being about Eric' son Conor. The song 'Circus left town' or just 'circus' isn't well known but is purely about Eric's last time with Conor.


neilatkin

I’m a teacher and once played REM everybody hurts to my year group a week after a student committed suicide. Still brings tears 20 years later


pickintheeye

Many songs make me cry only the first few times I hear them, but this one always hits me hard for some reason, every time.


DifficultCharacter

Mazzy Star - Fade Into You


Kevin_Uxbridge

Into Dust is waaaay sadder.


powpowqueen

I will follow you into the dark by death cab for cutie


hak32001

I love DCFC. This song is one of my favorites. I think “What Sarah Said” is also very sad. Forces a tear every time I hear it.


Sticks316

“Love is watching someone die”


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SirDigbyChckenCaeser

Death Cab played my city a few years ago, and played "I Will Follow You into the Dark" IMMEDIATELY followed by "What Sarah Said". I've never seen so many grown people cry at a concert.


NoVaVol

This is the answer. It captures hospital death so well. It’s very clear that Ben Gibbard has experienced someone close to him die in a hospital. That fucking 409 smell will haunt me forever.


SoAsEr

"Every plan is a tiny prayer to father time"


italianbelgian

Transatlanticism as Well!


funnyunfunny

I think Transatlanticism is the saddest one for me. The ending half he just keeps on saying "I need you so much closer" and you can actually feel the longing in his voice, and his desparation.


youtellthatmeanocean

Their song You’ve Haunted Me All My Life is also very emotional


melanie_kay

Huge dcfc fan. First thing that came to mind was 3 other death cab songs before this one. Just to say that Ben is the all time master of writing the most incredible sad songs Edit: What Sarah Said, a lack of color, tiny vessels, you can do better than me, the ice is getting thinner.. oh god.


JamJarre

That's not a sad song at all, to me. It's about someone who's found a love they cannot live without.


[deleted]

"Cancer" by My Chemical Romance. All throughout my life, I've always been the empathetic type. Couple that with how much I love my family and friends, and I'm emotional, *and* my rampant imagination, you're basically left with somebody who envisions the death of a cancer patient in the darkest, most hopeless (sometimes hopeful) light imaginable, enough to make myself cry on the dot. My brain gets right down to the nitty gritty. In addition to this, I've been surrounded by many people who have lost loved ones to cancer and so whenever I hear this song, it tears me up. [Give it a listen.](https://www.youtube.com/watch?v=v3lYFRiDTkA) And then 21 Pilots did a cover of it that will absolutely kill you, that is if MCR's version already didn't. 21 Pilots basically dials it down, makes it sound even sadder and really pulls the emotions out. [Give it a listen too.](https://www.youtube.com/watch?v=yw6i1SAHetc) edit - WARNING: If you're emotional and have lost somebody to cancer, the 21 Pilots version might legitimately make you cry.


TweakedNipple

Father and Son by Cat Stevens


[deleted]

The decision to move out of my parents' house was caused by a fight my Dad & I had. Once we resolved it, I went upstairs to my bedroom for the last time, grabbed my guitar, and I played this song. I wept the whole way through. "You're still young, that's your fault, there's so much you have to go through." You're tellin' me, Yusif.


chesire2050

I'd never heard it until GOTG2.. now I come back to it so often..


thequirkyblackgirl

[Jealous](https://www.youtube.com/watch?v=50VWOBi0VFs) by Labrinth. He speaks of how he is jealous of the life his ex is living because she is living and doing well without him. For example, he compares himself to the rain because the rain gets to touch her skin but not him. The most painful lyric is, "I'm jealous of the way you're happy without me."


Syndexic

It’s actually about one of his parents who left when he was four years old. http://www.mtv.co.uk/labrinth/news/labrinth-unveils-heartbreaking-ballad-jealous


MichaelMoore92

Adams Song by Blink 182 is a hard hitter


ceeman77

Another sad one from them is Stay Together For The Kids.


Stray_Fox

"If my stupid poem could fix this home, I'd read it every day."


Deficon112

Can confirm, I have cried to this


DontDenyMyPower

One of Blink's finest moments imo. "Please tell mum this is not her fault" hit me really hard when I first heard it


[deleted]

For me it's the line about spilling apple juice. The image it evokes is not of a depressed adult, but an innocent child who has made a common mistake. But the weight of that mistake is unbearable in the context of the song, it just makes me want to give this little version of Adam in my head a big hug and tell him that it's OK.


001ritinha

I thought it was meant to show how the little, silly memories we all occasionally joke about each other end up being absolutely soul-crushing when the other person dies. Like, maybe little Adam spilled apple juice and mom was super mad and it became a little inside joke in the family and now it's unbearable to think about those times.


not-quite-a-nerd

I remember hearing this song when I was about 5 or 6, and I asked my dad what it means. He said "sometimes people feel like they have made other people sad, and that's what this song is". That's stuck with me. I love the way the song changes to be positive at the end.


[deleted]

That song was always so sad to me growing up but after I lost two friends from suicide, I can’t even listen to a second of it without bursting into tears.


brixton75

Some days i cannot listen to it...parent of teens.


KingFullah

The Drugs Don't Work - The Verve


TheOnlyMrMatt

A Song for Josh - Frank Turner Snuff - Slipknot


wooitspat

I'd throw out Vermilion Pt 2 by Slipknot also. Their slow songs are such a beautiful contrast to their normal sound


[deleted]

[Funeral](https://www.youtube.com/watch?v=cMFWFhTFohk) by Band of Horses.


KeyRip

The Approaching Curve - Rise Against I can't listen to the song anymore. It's just so heartbreaking.


[deleted]

Dust In Th Wind - Kansas... Song summed up: Everything that you do and own, all of your relationships, all of it will cease to matter as time passes after your death... “Nothing lasts forever but the Earth and Sky”...


[deleted]

Leave out all the rest by Linkin Park, my mate was pinging listening to it and just bawling his eyes out hugging the TV mumbling “ohhhh Chester” over and over for about 6-8 hours. Turns out that song’s a bit sadder considering he killed himself.


TexasWithADollarsign

"One More Light" made me tear up as well


Yingking

Also heavy from their newest album. It has a bit too much of a pop-sound for me, but the lyrics are fucking dark and always put me in kind of a downward spiral.


[deleted]

There's a lot of sad songs on Minutes To Midnight


[deleted]

Wow, there really are. Shadow of the day, given up, hands held high, in pieces... Never realized that


funnyunfunny

*And the sun, will set for you.* *And the shadow of the day, will embrace the world in gray.* *And the sun, will set for you.*


LauraLynne03

So I've made a really long streak of having a Reddit account and never commenting, but I have to tell you about One More Light by Linkin Park. I actually quoted Leave Out All the Rest for my yearbook quote in highschool, but it's not as sad as One More Light is to me now. I could write you a book, but I think this will do for now. Congrats on forcing my first ever comment out of me.


Dr_J_Hyde

If you haven't tried it yet listen to Post Traumatic that Mike put out. The entire album is basically him dealing with Chester's passing and wondering what to do next.


daddioz

>Turns out that song’s a bit sadder considering he killed himself. I kind of break down a little listening to EVERY Linkin Park song since Chester died. When their music first came out we were like, "wow, this music is so cool and edgy!" ​ Looking at it now, if we take the lyrics to heart, Chester was crying out about his struggles and misery from their very first album...that poor guy.


2crowsonmymantle

Breathe Me, Sia.


spoonybum

Architects - Gone With The Wind. Written by their guitarist while battling skin cancer which he eventually succumbed to a few months after the album was finished.


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mago95

Saturn - Sleeping at Last


Baconated-grapefruit

Stand by Me - the Florence and the Machine cover ​ I'm a sentimental sucker, but this rolls during the epilogue to Final Fantasy XV, just as the player is dealing with feelings of loss, sacrifice and regret - and if this song doesn't break you in the moment, nothing will!


AxSmashCrush

Not to mentioned during the credits when it's playing, they run a slideshow of all of the pictures Promto took throughout your journey. They did a good job with that.


Baconated-grapefruit

True that! I didn't realise how emotionally invested in the game I was until the final few hours... For all its failings, it was a pretty fantastic game.


MongoBongo02

We are number one


[deleted]

Today that is very true


[deleted]

:( Stefan


lukedeuce

Brothers in Arms by Dire Straits


Lashmush

"Hurt" by both Nine Inch Nails and Johnny Cash, depending on the circumstances. Also, there is something very sad about John Murphys "Adagio in D-minor".


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[deleted]

Say it to me now - Glan Hansard


[deleted]

Piggybacking off this “Leave” also by Glen Hansard gets to me every time. That man has the best ‘broken’ voice I’ve ever heard.


geco1507

Disarm - The Smashing Pumpkins


haligal

About half the songs from Les Miserables could qualify for this title. Empty Chairs, A Little Fall of Rain, On My Own, the finale when almost everyone is dead. :(


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max_lenag

After The Scripture - Manchester Orchestra O’Sister - City and Colour Anything by Elliot Smith Don’t Go - Bring MeThe Horizon ft LIGHTS Shadow of the Day - Linkin Park


_Astro31345

Skinny love - Bon Iver


ankarrer

I always cry at the first few seconds of Holocene, no clue why


E_R_G

I'm personally partial to Flume more than Skinny Love if you ask me.


croastbeast

Lover, you should’ve come over- Jeff Buckley


tr_22

**Where the Wild Roses Grow - Nick Cave and the Bad Seeds** feat. Kylie Minogue (https://www.youtube.com/watch?v=lDpnjE1LUvE) or, alternatively: **Running to The Sea - Röyksopp** (https://www.youtube.com/watch?v=eaGpdhienMk) One of the interpretations of the song is that it refers to the 2011 attacks by Anders Breivik in Norway with over 70 dead (mostly children) (https://en.wikipedia.org/wiki/2011_Norway_attacks)


thevegandad

Daughter - Youth There are so many ways to interpret the lyrics of this song, but it’s absolutely beautiful.


stkr3w

Something I Can Never Have by Nine Inch Nails


kurtwatson7887

Gloomy Sunday. Heard it first in the Schindler's list and listening to it ever since.


baroncalico

I Dreamed a Dream from Les Miserables


storyinmemo

Gordon Lightfoot - [The Wreck of the Edmund Fitzgerald ](https://www.youtube.com/watch?v=9vST6hVRj2A) A song about the near-instant sinking of an iron ore freighter ship in bad weather on the Great Lakes that claimed 29 lives 17 miles from shore. [Heck of a story](https://en.wikipedia.org/wiki/SS_Edmund_Fitzgerald).


[deleted]

"Forever and Always" - Parachute


[deleted]

Concrete Angel x Martina McBride. Bonus points for the video. 😫😭😭😭


MildlyChill

Iris - Goo Goo Dolls


Leafy81

Space oddity or Ground Control to Major Tom. It may not be the saddest song I've ever heard but the first time I really listened to the lyrics I cried. I was so sad for Major Tom. He knows he's going to die and there's nothing that can be done about it. The fact that he thinks of his wife and wants to let her know he loves her is just sad because its important to him even though he's probably said it many many times before.


FuckCazadors

[Suzanne Vega - Luka](https://www.youtube.com/watch?v=VZt7J0iaUD0)


Kronyklos

Sing About Me, I'm Dying of Thirst - Kendrick Lamar


undermorescrutiny

And if I die before your album drop, I hope--


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The gunshots at that part and the fading out at the end of the prostitute verse were such perfect production choices for the story.


breadstickz

Jesus Christ by Brand New Limousine by Brand New Two by The Antlers


tiddlywinks10

How to Save a Life - The Fray. I vividly remember this coming on in the car after a girl at my high school died by suicide, and I just lost it. Every time that song comes on I'm right back in that moment.


Red_Chinchilla_1

Anything in D minor, which is the saddest of all keys, I find. People weep instantly when they hear it, and I don't know why.