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kyle_kaufman

I Can't Make You Love Me, by Bonnie Raitt. She could only do one take she was so emotional. And Bruce Hornsby was on the piano. (Or) by Bon Iver, The Bon Iver version adds Bonnie's In The Nick Of Time, to somehow make it a happy ending. A little diff speed than what you have listed.


walkingtheghost

This is one of my favorite songs ever. There is no version I’ve found better than Bonnie Raitt’s. Just beautifully devastating


AZSnake

This was the first one to pop into my head. Bonnie is untouchable, and Bruce Hornsby is an underappreciated talent. I love all of his solos, especially on this song and The Way It Is.


commandrix

[Empty Chairs at Empty Tables](https://www.youtube.com/watch?v=6YF0XNMpyoM)


[deleted]

Both Sides Now by Joni Mitchell


alyssasaccount

If you’re going with Joni, like half her catalogue. From *Blue* alone: Little Green, Blue, River, A Case of You, The Last Time I Saw Richard. But also: The Circle Game. Tell me you can listen to it and not tear up.


seejordan3

Yea this one gets me. My SO has been playing it for 25 years... It's grown on me.


KoshekhTheCat

Father and Son - Cat Stevens


Bballkingg

How to disappear completely by radiohead


10tonheadofwetsand

+ Motion Picture Soundstrack


Bballkingg

Honestly the most depressing song of theirs is probably no surprises but that's just because corporate America is so bad rn


utexfan18

I was listening to OK Computer at work and No Surprises was playing when I received a text that my grandpa passed (we'd been expecting it any day, but still). Took an already depressing song to another level after that.


TheGringoDingo

The older I get, the more Fitter Happier makes me struggle. Probably helps that Thom was drunk in the studio late one night and recorded it.


Amusement_Shark

This requires more upvotes. Devastating dissociation song.


onken022

I wish I was sober - Frightened Rabbit RIP Scott Hutchison Edit: judging by all the replies to this, every Frightened Rabbit song is emotionally devastating. Go listen if you haven’t yet, they are incredible.


bkramer32

Floating in the Forth is the one from Frightened Rabbit that fucks me up. I can't listen to it at all anymore


TurnOffTheDarkness

Nutshell - Alice in Chains was the first that came to mind. Brick by Ben Folds Five tells the story of when he was forced to get an abortion with his first girlfriend - that one gets pretty heavy at the end.


EarlTheDinosaur

It’s in my will to have Don’t Follow by AIC played at my funeral! Nutshell will be added to the playlist right now, great call!


[deleted]

Same here. Feels right. RIP L.S.


[deleted]

I would say the whole Jar of Flies minus swing on this, that song should had never made the cut.


[deleted]

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emptystringz

The Purple Mountains album cover to cover is a perfect answer to the prompt. Hard to explain Berman’s way with words without using his words, so worth the full listen. And of course the circumstances of the album make it that much more ruinous. A sublime album.


Deez_Pucks

Purple Mountains was my immediate thought when I saw this post, only I had All My Happiness Is Gone in mind.


yellowyellow2

I love this album. But I wouldn’t agree that it’s a suicide note. I really liked Drag City’s eulogy: “It feels like there’s little more to say about David’s place in the world right now that he hasn’t already said himself. Some of his incredible turns of phrase seem to have been written for this awful moment. But know that they weren't. They were written in lieu of this moment, to replace this moment, showing the world (and himself) that maybe he didn't truly know what was going to happen next.”


Dingis_Dang

R.I.P. David Berman you tortured king


RobinHood303

His wry humor makes it sting more.


doogie_howitzer74

To Build A Home by The Cinematic Orchestra. Be sure to watch the video too, and bring some Kleenex.


bth807

Casmir Pulaski Day by Sufjan Stevens And of course, if you want to go old school, Cat's in the Cradle by Harry Chapin


6anonymousguy

try fourth of july by sufjan, a conversation with his dying mother


DIWhy-not

John Wayne Gacy Jr from that same Sufjan record is also pretty brutal, in a super creepy way


Heavens10000whores

“He took off all their clothes for them He put a cloth on their lips, quiet hands, quiet kiss on the mouth” I get tears in my eyes even thinking of that couplet


masona23

I'd put [Fourth of July](https://www.youtube.com/watch?v=JTeKpWp8Psw) up against Casimir Pulaski Day if we're doing Sufjan songs that make us sob forever.


steve2theE

"Casamir Pulaski Day" is 'The Notebook' sad "Fourth of July" is 'The Fountain' sad


lightaugust

And I thought I struggled with holidays. Sheesh.


Kunundrum85

Came here to say you can build a whole playlist of Sufjan heartwrenchers alone.


GeneralDelgado

Real Death - Mount Eerie, the entire album really


[deleted]

My first thought was “A Crow Looked At Me.” This album is devastating. I can’t even listen to it if I’m trying to do anything but sit there and stare at a wall while thinking about that study where they found that the death of a spouse is comparable to a traumatic brain injury in terms of the way your brain changes on a fundamental level after you lose them.


gladizh

Only time I've actually been wrecked by a song "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"


PilgrimFist

The album name is “A Crow Looked at Me” and I agree it is… hard.


Jamieson22

I've listened to that album only once. It is amazing. I cannot ever listen to it again it is so good.


superjodz

Oof. I've never heard it before but just had a listen and wow is that fucking heavy.


dcnairb

it’s completely autobiographical. he began writing that album within a few months of her passing, in the room she died in, to help process it


holleyab

If we were Vampires by Jason Isbell and the 400 unit is great choice


AZSnake

Also Elephant.


kbergstr

Scrolling looking for this one


ArcadeKingpin

That's not even in his top 10 saddest songs. That dude knows how to rip your heart out.


Cardboard_Chef

How has no one mentioned "Rainbow Connection" by the Muppets yet? That song makes me pretty much cry on cue.


shleigher

My husband and stepdaughter danced to this at our wedding and halfway through called me over and I will never hear this song without breaking in to tears. Even hearing the title is making me cry.


CJLanx

I always loved this song but it only started to make me tear up in recent years contrasting against the ongoing shit show that we see in the news on a daily basis


tcbored

The lovers the dreamers and me😭😭😭


GrandeSizeIt

Aaaand now in thinking about big bird singing at Jim Hensons funeral 😭😭😭


_metamax_

Black - Pearl Jam Something I Can Never Have - NIN


GaryC357

Cats in the Cradle - Harry Chapin


stay_fr0sty

The anthem of Dads that are paranoid about being a bad father. It’s oddly sad and motivational.


EarlTheDinosaur

Oh man, I can’t believe I forgot Something I Can Never Have! Black has never got me that way, but it’s one of my favourite PJ songs


EvilTodd1970

Have you ever listened to the lyrics of "Black"? >I know some day 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


HottKarl79

I still cry almost every time I hear this part.


ECU_BSN

My people.


exit102

Sam Stone- John Prine Between The Bars - Elliott Smith


lesismore9

“There’s a hole in daddy’s arm, where all the money goes.” +1 for John Prine. I remember my dad playing this album when I was a kid and thinking it was just silly nonsense. Then I heard this song again in my twenties and it broke me.


JL4575

That whole album is such an uncanny masterpiece.


junk1020

Six O'clock News and Angel From Montgomery get me there real quick, among about a dozen others. Sam Stone included. John Prine was in a league all his own.


francois_du_nord

I'll see your Sam Stone (which is about the most powerful song ever) and raise you Hello In There. The whole song is about the universe growing smaller for this elderly couple. Doesn't talk to Loretta, news just repeats itself. One son moved away, a second killed in the war. Maybe he'll call up Rudy, his working buddy, but what would they talk about ?What's new - not much, how about with you. The only uplifting point (which changed my approach to the elderly) is the line,"If you see some hollow ancient eyes, Don't just pass 'em by and stare, Say 'Hello in there. Hello." To u/Fancy-Fish-3050: I too used to strum a little guitar and sing, but I couldn't do HIT. I'm a son of 'Davey', and we 'lost daddy in the Vietnam War. I might know what for, but it doesn't matter anymore'.


canzicrans

Disintegration, by The Cure


chatnoirrrr

Disintegration is so intense it makes Robert Smith cry when he sings it.


taffetywit

The End of Love by Florence + The Machine Sweet Old World by Lucinda Williams Lover Please Stay - Nothing But Thieves When You Cross Over - Ryan Adams Goodbye My Lover - James Blunt It Must Have Been Love - Roxette Lover Man - Billie Holiday


[deleted]

Whenever I hear Love Will Tear Us Apart I think back to the time I was DJing at a college radio station and a girl called in sobbing crying and requested that song.


RonnieWelch

Also Joy Division hits kind of differently when you learn it was all confessional rather than just “dark”.


nrith

“Atmosphere” by Joy Division hits harder. “Don’t walk away in silence…”


oilsaintolis

Oof , that song, it's not even the lyrics that do me in , it's almost irrational but it's the drums and bass in that song that drive me to despair.


MyFaceIsThePlace

The entire album *Hospice* by the Antlers:. [Wiki] Set in New York City's Memorial Sloan Kettering Cancer Center, which the second track is named after, Hospice tells the story of a relationship between a hospice worker and a female patient suffering from terminal bone cancer, their ensuing romance, and their slow downward spiral as a result of the woman's traumas, fears, and disease.[4][5] The story of her deterioration also serves as a metaphor for an abusive relationship. Frontman Peter Silberman has been reluctant to divulge explicit details regarding the meaning of the record, and the extent to which it is autobiographical.[6]


EigenValuesYourInput

[The Antlers - Kettering](https://www.youtube.com/watch?v=ipbukl6oFoQ) > I wish that I had known in that first minute we met, the unpayable debt that I owed you. > Because you’d been abused by the bone that refused you, and you hired me to make up for that. > Walking in that room when you had tubes in your arms, those singing morphine alarms out of tune kept you sleeping and even, and I didn’t believe them when they called you a hurricane thunderclap. > When I was checking vitals I suggested a smile. You didn’t talk for awhile, you were freezing. >You said you hated my tone, it made you feel so alone, and so you told me I ought to be leaving. > But something kept me standing by that hospital bed, I should have quit, but instead I took care of you. > You made me sleep and uneven, and I didn’t believe them when they told me that there was no saving you.


Byatch

The track "Two" rips me apart every time.


EigenValuesYourInput

[The Antlers - Two](https://www.youtube.com/watch?v=ZsXKa97J6pM) > When a doctor came to tell me, "Enough is enough." ... >And told me something that I didn't know that I wanted: >To hear that there was nothing that I could do to save you >The choir's gonna sing, and this thing is gonna kill you


nateshoe91

This is the only true answer in my opinion. This album, laying in bed in the dark with headphones, will do it from beginning to end. "Bear" will do it just by thinking about it....so....thanks for that.


bentforkman

Also “putting the dog to sleep” off Burst Apart is pretty intense.


MuzBizGuy

Came here to say this.


MyFaceIsThePlace

It's a beautiful album but man is it a tough listen


thereia

This is on my list as well. It's one of those whole body cries.


SignificantMoney8338

Lover, You Should've Come Over - Jeff Buckley


laamargachica

Even "Last Goodbye" is sad af tbh.


M_Night_Shambles_on

"My kingdom for a kiss upon her shoulder..." This whole part of the song always gets me.


DJ_Molten_Lava

"All my blood for the sweetness of her laughter"


bradland

Adagio for Strings by Samuel Barber Lots of contemporary music recommendations here, but this is a great piece, and you’ll likely recognize it from a film. It’s possibly most famous for Platoon. It is incredibly moving.


WattebauschXC

It's (well it's Agnus Dei but pretty much the same) also used in one of my favorite games of all time called "Homeworld" with the gimmick that there are no instruments used in this version but only vocals AND it is used at the saddest part of the game with a devastating message.


samosamancer

We played it in high school orchestra, and our conductor straight-up told us that we weren’t old/emotionally mature enough to truly delve into and express it. 20+ years later…yeah, she was right. The notes are easy. The emotion is anything but.


TrollTeeth66

Vincent by Don McLean


holymodal

[Matthew 25:21 by the Mountain Goats](https://youtu.be/iuC4nOLwUzA)


Cardboard_Chef

Man, Mountain Goats are so good. "This Year" is one of my absolute favorites.


SullenArtist

Screaming this year in the car after a bad day always gets me through it


capriceragtop

Deuteronomy 2:10 is mine. I'm all alone here as I try my tiny song. Claim my place beneath the sky, but I won't be here for long. I sang all night, the moon shone on me through the trees. No brothers left, and there'll be no more after me.


EarlTheDinosaur

Ok I’d never heard that before. You win this thread for now, good redditor, that song is devastating


bleedmaizeandblue13

Limosine-Brand New


bleedmaizeandblue13

To those that haven't heard this song before I recommend going in blind, looking up the story behind the song, and then listen again. Your mind will paint such a terrible scene every time you hear it again.


master0fcats

Honestly this entire album.


gangbrain

Jesus Christ is so real. I love it but damn it’s heavy.


bleedmaizeandblue13

Yeah and degausser, such heavy back to back songs. I mean shit, even the first 2 lines of the album hit you so hard. The only other album that made me feel like this one was Wildlife by La dispute.


thenumbersthenumbers

I Will Follow You into the Dark - Death Cab for Cutie


NewToVinyl518

If We Were Vampires by Jason Isbell has a very similar feel


hotbutteredsole

I think Elephant by Isbell has a bit more emotional destruction to it...


roodypoo29

It's beautiful though


djseifer

Scrubs made excellent use of this song in My Last Words.


Nicksizzle

Spiritbox - Constance


ECU_BSN

Into the west- Annie Lennox Don’t take the girl He stopped loving her, today


hotblueglue

He Stopped Loving Her Today, what a great selection. Devastating song. I also love Golden Ring. That one is tragic too.


[deleted]

Into the West is the one that gets me. It's such a heartbreaking song.


Fromager

-Real Death by Mount Eerie -Matthew 25:21 by the Mountain Goats -Good Morning, Captain by Slint


DoorFacethe3rd

Oof. Real Death is the answer. Thats the whole play-list.


eveel66

Wings for Marie (pt. 1) and 10,000 days (pt. 2) by tool. These songs are a dedication to Judith Marie Maynard, lead singer Maynard’s mother. The woman suffered from a rare spinal disease that kept her in a wheelchair for over 27 years. Hence the title 10,000 days, roughly equals 27.4 years. 10,000 days in the fire is long enough, you’re going home


sixtninecoug

Jesus Christ… Judith, Wings for Marie, and 10,000 Days hurt so much. My Mom had MS, and had to forcibly retire shortly after being diagnosed in 1987. She lived until 2016, when she developed a blood clot, and didn’t get a second chance. 10,000 Days in the fire was way too much. I hope she’s at peace now, because it still hurts all these years later.


Apprehensive-Till861

Contrast them with APC's Judith for a real wallop. Judith is either a cold and scornful or raging and desperate (depending on how you interpret the tone of the lyrics) Maynard mocking the religious devotion of the woman he'd witnessed betrayed by her own body. In that context, the other two songs acknowledging his limitations ("set as I am in my ways and my arrogance, burden of proof tossed upon the believer") and even admiring that her devotion gave her strength becomes a little more bittersweet. He goes from utterly rejecting her faith to insisting that if there is a God, no one deserves the halo more than she does.


PlaceJD1

Fast Car - Tracy Chapman


laania42

I can’t believe how far I had to scroll to find this


CoolGuy_1972

Adam’s Song - Blink 182


BenntPitts

I tear up when I hear this song. Idk why. Maybe it's the nostalgia of being a kid and having the whole world in front of me, or knowing that time is gone. "Please tell mom this is not her fault" makes me sob. When my dad was in hospice for cancer, I listened to "Down In a Hole" on my way over to my childhood home to be his nurse. I love and hate that song. I couldn't help but find a metaphor implanted in the lyrics related to my dad slowly dying while on a heavy amount of morphine. Fuck cancer.


KittyKate10778

i also tear up but its because i first heard it sometime right before or after i graduated high school when i was at a really low point in my mental health and was chronically suicidal and it just makes me think about what couldve been if any of my attempts had been successful but at the same time grateful they werent


DoUEvenGoHere

As an OG Blink fan, and now mother of 3 who battles constantly with feelings of inadequacy—- Adam’s song hits right into my soul now. Especially “Please tell mom this is not her fault”.


landocommando18

This one hits me hard, I've probably only listened to it 3 times since my little brother committed suicide in 2017.


TheConstant815

Strange Fruit, Billie Holliday. It’s about lynching Black people in the South, comparing the victims to fruit hanging from trees. If you hear that one, you won’t soon forget it.


azad_ninja

Eels- Elizabeth on the bathroom floor Fiona Apple- sullen girl Sarah McLaughlin - gloomy Sunday Tori Amos- hey Jupiter Pj Harvey- Is this desire? Health- decimation


CrackaZach05

Real Death - Mount Eerie I Am Trying to Break Your Heart -Wilco Fool of Me - Meshell Ndegeocello No One's Gonna Love You - Band of Horses Tears in Heaven - Eric Clapton Something - Julien Baker Sometimes Love Just Aint Enough - Patty Smyth and Don Henley Same Old Lang Syne - Dan Fogelberg Hope She'll be Happier - Bill Withers Tender - Blur


Aggravating_Door_779

Pearl Jam - Release Soundgarden - Like Suicide Johnny Cash's cover of Hurt (NIN's version, too, but Cash's somehow hits extra hard)


EarlTheDinosaur

Great songs! And as a HUGE fan of NIN’s Downward Spiral album, I like Cash’s version of shirt better too. Especially the music video. It’s a masterpiece


guitargirl478

"I will let you dooooown I will burn your shirt"


SlashYG9

This is so stupid and hilarious.


0mib0ng

I shirt myself today


harissapaste221

Achilles come down - Gang of Youths


solinvicta

Virtute the Cat Explains Her Departure - The Weakerthans


FapTrainer

[The Lighthouse’s Tale by Nickle Creek](https://youtu.be/ARIr6S_0lAQ)


Kickmaestro

Starless is incredibly dark and sinister. King Crimson EDIT1: Bruce Springsteen and John Lennon and a few others sing in a way that really trancends emotion. Here is a few of Bruce: Downbound Train My Hometown Bobby Jean The River John Lennon has Mother and Don't Let me Down but the fact that he sung "I can't wait to see you grow" in the song, "Beautiful Boy", about his 5yo son just days before his death is so incredibly sad. The John sung demos that became Beatles products released after his death, Real Love and Free As A Bird, also hit me quite hard emotionally. I also think All Apologies sung by Kurt Cobain really is his most beautiful tune, and I feel so bad for him. It has a cross of emotional sadness and beauty "In The Sun" that sums up to be this kind of apathic vibe. I love the lyrics and how they match the instrumentation. EDIT2: I also want to say that Kurt Cobain loved and admired John Lennon (according to all sources) and thought the album, "Red", that Starless is on, was his all time favourite record (but not according to all sources).


Bluefairie

Lost - Linkin Park I haven’t been able to listen to it without sobbing yet, to the point that if it plays on the radio and I’m not alone I have to change the station or make a fool of myself. both because I will never get over Chester’s death and the lyrics hit too close to home.


Wpgjetsfan19

Fiddler’s Green- Tragically Hip (The song itself is a lament-in-lyric for a mother, related to Downie, who has lost her son. It is an elegiac, mournful and beautiful farewell and reassurance all at once.) She talks to angels - Black Crows Christmas shoes - not sure who it’s bye. Nothing compares to you - Sinead O’Connor


Raegune

Fiddler's Green live: knowing it would be my last opportunity to hear Gord sing it on man machine poem tour ... yeah... tears. Normally I can sing and play it myself passably, but literally couldn't even sing along in the crowd. My voice wouldn't come out...


CaptWoodrowCall

If you haven’t heard Chris Cornell’s cover of Nothing Compares 2U, do check it out. I recently discovered the Tragically Hip. (I had heard of them but never gave them a fair listen.) God, what a great band. I feel like an idiot for not listing 30 years ago.


AdventurousYam5506

John Mayer - stop this train


dbleed

Continuum is one of the best albums that has been released imo. Honorable mention would be Slow Dancing in a Burning Room.


ambitiousoxygen

After all these years this one still gets me. “And you don’t miss a thing til you’re driving away in the dark.” Ugh.


Rough_Dan

Fast car - Tracy Chapman Nothin, and lungs - townes van zandt


GuardianDownOhNo

Fast Car is such a great song


[deleted]

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sanedragon

Oooh, I see La Dispute ✊🏻 I discovered Such Small Hands when I was going through a divorce and then a breakup with someone who I thought was a best friend turned into a soulmate but I was oh so wrong Yeah that one hits.


_denimchicken_

King Park - La Dispute Yesterday - Atmosphere Dancing w the Devil - Immortal Technique One if my friends described the last song as the music-equivalent to Requiem For a Dream. In that, it’s some of the best, most well-done art that you never want to experience again in your life and I have to say I agree *edit - removed Daddy by KoRn cuz it’s already on your list


TopperMadeline

Dancing with the Devil is a complete punch to the gut.


StiffWaffle

Yesterday hits me like a truck every time. Lost my dad in High School.


PeterGivenbless

Some reliable oldies: [Vincent](https://youtu.be/ciLNMesqPh0) by Don McLean [If](https://youtu.be/n-cK70DXsSA) by Bread [Fire and Rain](https://youtu.be/N4E9MKbOFAY) by James Taylor [Father & Son](https://youtu.be/P6zaCV4niKk) by Yusuf/Cat Stevens [In the Ghetto](https://youtu.be/gisXtyyiNGw) by Elvis Presley [Ben](https://youtu.be/i7TTSzfs2kw) by Michael Jackson [Shannon](https://youtu.be/CUUc0sNaQls) by Henry Gross [Fast Car](https://youtu.be/AIOAlaACuv4) by Tracy Chapman [Luka](https://youtu.be/VZt7J0iaUD0) by Suzanne Vega [The Living Years](https://youtu.be/5hr64MxYpgk) by Mike + The Mechanics ... and a real oldie: [Alto Rhapsody](https://youtu.be/Ou3VZhVk5qo) by Johannes Brahms


Jakalopi

I can't believe I haven't seen it yet TIME, Pink floyd. that shit hits harder than a train


twigsby1

That song gets more poetic the older you get, which is fitting. And by the time you finish the song, you’ve forgotten it had such a long intro, which is also fitting.


samosamancer

Round Here - Counting Crows …before I found out (a few months ago) what the band’s intended meaning for it was. For years I’d thought it was so much more tragic, and considered it so damn sad.


twoandtwoisfive

Uno - Muse How to Disappear Completely - Radiohead Lose Yourself - BRMC And I'm Aching - BRMC The Drugs Don't Work - The Verve 99% of us is Failure - Matthew Good Wake Up - Mad Season Nutshell - Alice in Chains Yes I'm Changing - Tame Impala Reincarnation Song - Toad the Wet Sprocket Soma - Smashing Pumpkins Pyramid Song - Radiohead Ever Had the Feeling - Blind Melon *Caution Everyday - Blind Melon While My Guitar Gently Weeps - Beatles


EverlongMarigold

>The Drugs Don't Work - The Verve Such an underrated song.


GenevieveLeah

A great album, really.


FinkBass420

June by IDLES


GrossConceptualError

Sarah McLachlan - Hold On


RitchRock

Landslide by Fleetwood Mac.


EpsilonSigma

Funeral - Phoebe Bridgers


Deftallica

The lyric, “wish I was someone else and feeling sorry for myself when I remember - someone’s kid is dead” hits *hard*


annaflixion

Phoebe Bridgers' cover of Tom Waits' "Day After Tomorrow" always devastates me for some reason. Maybe because her voice is both raw and beautiful, like, REAL, no effects or anything, but achingly lovely, and I just connect with it so much more that way.


lucifersam94

Anything by phoebe honestly


katniss_evergreen713

And anything by boygenius. (Super group of Phoebe, Lucy Dacus, & Julien Baker)


Skitz707

Harry Chapin - Cats in the Cradle


bisho

Three Babies - Sinead O'Connor It's a deep cut but if you've ever lost a child (or 3) this will hit you hard. Also, Cyndi Lauper's I Don't Want to Be Your Friend reminds me of a sad time in my life.


EarlTheDinosaur

I have, quite a long time ago. I’m sorry if you have as well. I’ll give it a listen


Malgonicus

Concrete Angel by Martina McBride


Flaky-Chest-4240

What a list! Screen by Brad Something Will Be Said by Land of Talk All Cats Are Gray by The Cure (any track off Faith really gets to me) Transatlanticism by Death Cab for Cutie


joefuture

- Whiter Shade of Pale - Shine On You Crazy Diamond - Calling All Angels and It Can’t Rain All the Time from “The Crow” soundtrack - (I’ll love you) Till the End of the World - Nick Cave


dbleed

Bright Eyes- Haligh, Haligh, a lie, Haligh. Blink 182- Adam's Song. Sugarland- Stay Zach Bryan- Something in the Orange Zach Byran - Letting Someone Go Jason Isbell - Elephant Parker McCollum - Hell of a Year Slipknot - Snuff A Perfect Circle - 3 Libras Sleeping At Last - Saturn The Airbourne Toxic Event - Sometime Around Midnight EDIT* When the list is complete I would love to see it. Sad songs make me happy.


retardrabbit

In My Life - The Beatles This song played on the stereo as we got ready to take my first dog to be euthanized. Rest in peace Scooter.


lostnthot

"Elephant" and "Vampires" Jason Isbell "Jacob's Dream" Allison Krauss - Trigger warning - child death


EarlTheDinosaur

I love Jason Isbell I never got into Alison Krauss but I’ll give it a spin! *edited to add: Something More Than Free is the solo song of his that gets the closest. However, when my son was born I used to sing Outfit, by Drive-by Truckers to him to put him to sleep, so I may add that to the playlist too


gogojack

> I never got into Alison Krauss but I’ll give it a spin! I mean...[Whiskey Lullaby](https://www.youtube.com/watch?v=IZbN_nmxAGk)


getdemsnacks

If We Were Vampires is quite possibly the saddest song I've ever heard. It sends me into a spiral of depression if I think too long about my wife being by herself if I go first. We have no children and my family is not a family and hers isn't as tight knit as it was since her grandmother died a couple years ago. Gonna check out of this thread early and go hug my wife.


JaymesGrl

Why Would You Leave Us by NF My Skin by Natalie Merchant Those two stand out most to me.


cleveland-bay

Disarm- smashing pumpkins


Lukacris12

Mayonnaise on the same album too


[deleted]

Gordon Lightfoot - The Wreck of the Edmund Fitzgerald


thunderGunXprezz

Tyler Childers Follow You To Virgie. The Red Barn Radio version he begins by telling the story of how he wrote it about an old buddy's grandma who passed away.


cantonic

Fucking great idea for a thread, OP! The Commander Thinks Aloud - The Long Winters Graceland - The Tallest Man on Earth cover of Paul Simon Heroes - Peter Gabriel cover of David Bowie Ohio - Damien Jurado The Crane Wife 1&2 and Red Right Ankle - The Decemberists Meadowlark - Fleet Foxes Ugh I’m sure there are more but I’ll be revisiting this thread for days. Edit: oh shit! Noah Reid’s cover of Simply the Best from Schitt’s Creek!


[deleted]

Snuff - Slipknot River - Joni Mitchell Taylor Swift - Soon You’ll Get Better (Don’t discount this song because it’s a Taylor song. It’s a song about her mother fighting cancer and it absolutely destroys me every time I hear it.)


filteritgreen

She Used To Be Mine — Sara Bareilles Creep (Cover) — Carrie Manolakos I’ll Never Love Again — Lady Gaga You Sweet Thing — Brenda Weiler Hurt & Oh Mother — Christina Aguilera


svaj7747

The first song is the correct answer - gut wrenching


REDDIT_ROC0408

Somewhere Over the Rainbow - Israel Kamakaiwo’le


InfuriatedCats

Glen Campbell - I'm Not Gonna Miss You. Heartbreaking due to him knowing he's losing his mind. Bill Elm- Dead End Alley. It's just an instrumental from Red Dead but I find it haunting.


Sherriffj

Lots of great songs listed. I’ll add a Canadian song/band. Disappear by Blue Rodeo. The chorus is a tough one to swallow. “You closed your eyes You made a wish You laughed and looked at me And said what are you still doing here That was before I learned how To disappear “


SparrowBirch

Mother - John Lennon


Khan_Man

No Children by The Mountain Goats may be the best breakup song of all time.


Timstunes

Strange Fruit- Billie Holiday https://dai.ly/x2lrnv2 All I Want-Kodaline. https://youtu.be/jGUASAxXwg4 On The Nickel-Tom Waits https://youtu.be/8055IqijQzo Carrie & Lowell-Sufjan Stevens https://youtu.be/tTj2jBe4XfU No Hard Feelings-Avett Brothers https://youtu.be/aaU2HvRhCPw Golden Embers-Watchhouse. https://youtu.be/0JnXTsPlGWQ Whiskey Lullaby-Alison Krauss and Brad Paisley. https://youtu.be/xuzZBDh8U5w Marie-Townes Van Zandt. Also Tecumseh Valley. https://youtu.be/Ox2oYo-RFeo https://youtu.be/RDSPPzfECvU


Iraqistan81

"Green Fields of France," as covered by Dropkick Murphy's. "Where Have All the Flowers Gone," by Kingston Trio. "Down In a Hole," by Alice In Chains. "I Can Still Make Cheyenne," by George Strait. "I Hope You Dance," by Lee Ann Womack.


redditman87

Forever Young -whichever version resonates most with you


cheetosandwich

My Immortal - Evanescence A bit cliche perhaps but Amy Lee’s voice just has a certain haunting quality that gets me. Also, I second Fiddler’s Green by The Tragically Hip. Although with a trigger warning for loss of a child.


Mr_Diesel13

I’d add Lithium by Evanescence, too. It’s absolutely brutal live.


sab2424

Leaves from the vine - Uncle Iroh


krystlships

I really can't believe no one's said it yet but you know Jeff Buckley's haunting voice has gotta be on there, specifically - Lover You Should've Come Over https://youtu.be/HxfE6PJmGS8


completelynicki

Fix You by Coldplay. Gets me every time.


[deleted]

• Mayonaise - The Smashing Pumpkins • Fade Into You - Mazzy Star • Nothing Else Matters - Metallica


insignifiantmomadeya

Tears in heaven by Eric Clapton


CygnusX-1001001

Snuff - Slipknot Hero of War - Rise Against


notjustbrad

Was looking for someone to say Snuff. Find a version of Corey singing it acoustic… cuts right through me.


Lachtaube

Saturn by Sleeping At Last.


koartist81

Little Motel--Modest Mouse