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No_Abbreviations7366

Radiohead - How to Disappear Completely


Xys

Also : True Love Waits (AMSP version)


BoCoPo

Weird fishes


katofearth

I usually don’t think that anyone can cover Radiohead and do it justice, but Lianne La Havas does an amaaaazing cover of Weird Fishes


clozepin

Cats in the Cradle - Harry Chapin. It’s not ugly cry sad, but it’s “life is unintentionally sad” sad.


scott3387

Hits different when you have children as well.


gwaydms

I thought it was sad before I had kids.


floydopedia

I like the Ugly Kid Joe version because it starts off quiet and melodic then gets angrier/resentful in the middle - because that’s how I feel every time I hear it.


justforbru

Lost my Dad recently. Still ugly cried.


clozepin

Sorry, man.


justablueballoon

I can’t make you love me (if you don’t) - Bonnie Raitt


tinyplumb

The Justin Vernon versions are good too, or him Sean Carey in the jagjaguar sessions.


BoomerReid

This.


Willow-girl

I heard she recorded that in one take. Nailed it!


The_Scrabbler

Between the Bars - Elliot Smith


juiceboxheero

*"He said some weird stuff to me earlier. The kind of stuff you'd hear in a sad Creed song. Or a happy Elliott Smith song."*


reamkore

One of many Elliott Smith songs that totally qualify.


Akindmachine

Kings Crossing for me


Grand-wazoo

Also - I Didn't Understand


beast_yard

For sure. And Twilight because it is so eternally sad.


chinstrap

As an alcoholic, I find this song to be terrifying, not sad


MeatTornadoLove

As a recovering dope fiend I gotta revel in it and say thank fuck that ain’t me. Its like watching Drugstore Cowboy or Trainspotting I just sit there and think fucking christ I was boring and gross.


chinstrap

Word. I'd be dead if I had kept drinking. I tell people if they want to know what the last couple of years were like, down a bottle or two of Robitussun, put on a pot of strong coffee, and stay up all night with Either/Or on repeat.


scottyd035ntknow

Same... Quit cold turkey and it's been a year. I'm still sometimes amazed how much better life is. Shit is poison.


chinstrap

It's not so bad, if you are the kind of person who has two or three drinks and truly does not want any more. But that is not me.


Musicguy1982

"Last Call" for me


SameArtichoke8913

Love Will Tear Us Apart by Joy Division.


[deleted]

[удалено]


Miserable_Race6751

Whiskey Lullaby - brad paisley and Allison Krauss Elephant - Jason Isbell 


100YearsAndCounting

>Elephant - Jason Isbell  Always my first thought when this question is posted here. Also: 1952 Vincent Black Lightning - Richard Thompson Napoleon Solo - At the Drive-In


veepeedeepee

Sam Stone - John Prine


Butterbean4lyf

I had to scroll way too far for this. Talk about truly heartbreaking instead of your typical, sappy love heartbreak song.


slayer991

Terry Jacks - Seasons in the Sun Eric Clapton - Tears in Heaven and I'd contend that Pearl Jam's "Black" is one of the most brutal and raw break up songs ever.


bpdmeatbag

Love Of My Life - Queen The Night We Met - Lord Huron Leave Me Alone - Trashcan Sinatras Goodbye Mr. Blue - Father John Misty Baby As You Turn Away - Bee Gees I’m Sorry - John Denver Lover’s Cross - Jim Croce When She Loved Me - Sarah McLachlan I Just Don’t Think I’ll Ever Get Over You - Colin Hay Late For The Sky - Jackson Browne Beloved Wife - Natalie Merchant Only Once - Maria McKee Sam Stone - John Prine Wings For Marie, Pt. 1 / 10,000 Days (Wings For Marie, Pt. 2) - Tool It’s Easier - John Grant Black - Pearl Jam Please Don’t Die - Father John Misty St. Peter’s Autograph - Jason Isbell and the 400 Unit Elephant - Jason Isbell He Stopped Loving Her Today - George Jones For a Dancer - Jackson Browne Songbird - Fleetwood Mac Throw Your Arms Around Me - Mark Seymour / Hunters and Collectors White Wine In The Sun - Tim Minchin (Not really a sad song per se, but I can't get through it without shedding at least a tear or two. It's sentimental and just a simple, yet beautiful tune.) Everybody Hurts - R.E.M.


TraceyTurnblat

Love of my Life got the upvote here


decentlyfair

Night we met is class. Was lucky enough to see LH when they came to uk and incidentally will see them again this summer


sptfire

Wings For Marie, yeah


Rossticles

To add to the Tool listing: "Judith" by Maynard's other band, A Perfect Circle, is an equally great and sad song. It's about the same subject; his mom.


Zoe_Hamm

"Nothing Compares 2U" Sinéad O'Connor


Jappy_toutou

Since his death, Chris Cornell's version also gets to me hard...


[deleted]

I saw him do it live like 3 days after Prince died from an OD. I went to the show with my husband and we both just absolutely bawled ;The entire venue was crying . I’m an atheist but it felt spiritual


GoldenPoncho812

Written by Prince. Miss him dearly.


CarbonTrebles

Sometimes it Snows in April can hit hard for Prince fans.


Last-Juggernaut4664

Landslide - Fleetwood Mac


RunawayPenguin89

Wondered how far down my depression song would be!


cheandbis

Alone Again, Naturally - Gilbert O'Sullivan


predat3d

I don't know of another song of that era with explicit suicidal ideation 


heffel77

Suicide is Painless by Johnny Mandel


ForsakenHelicopter66

Was that used as the MASH theme?


HereAgainWeGoAgain

Yes


kballs

An absolute classic. Love Gilbert.


fishingboatproceeds

Casimir Pulaski Day - Sufjan Stevens Go Home - Julien Baker


palim93

Sufjan feels like cheating on this topic, so many sad songs. Casimir Pulaski Day takes the cake though.


fishingboatproceeds

It really does 😅 thanks for the spelling correction!


palim93

No worries, no one ever accused polish names of being easy to spell lol.


Snoo_73402

Casimir Pulaski day on the way to the office this morning got me.


yepperdrpepper

The Wreck of the Edmond Fitzgerald.


palim93

“Does anyone know where the love of god goes when the waves turn minutes to hours?” That line gets me every time. I live on Lake Superior and this song hits different looking out over the lake to where the Fitz went down.


nicunta

Superior is a wild beast who deserves utmost respect. Living on the lake is different. I miss it.


jasmineandjewel

Please please please take my upvote!


MotherInternet9091

Brand New - Play Crack The Sky


rustys_shackled_ford

Your tounge is the rudder, it steers the whole ship.


nothinqness

God this song gives me goosebumps


porksandrecreation

This Woman’s Work - Kate Bush I Can’t Make You Love Me - Bonnie Raitt


Zestymonserellastick

10,000 days / Wings for Marie part 2 - Tool It's heavy prog rock, but it's about the loss of Maynard's Mother. She was paralyzed for roughly 10,000 days before she died. 10,000 days is long enough, you're going home.


flodge123

You missed all the good ones: Heaven Knows I'm Miserable Now - The Smiths Back to Black - Amy Winehouse Mr Bojangles - Nina Simone Pictures of You - The Cure


KermitTheArgonian

"Gloomy Sunday" - Billie Holiday


superstaticgirl

Also "Strange Fruit". Which is also scary and anger making.


Jumpy_Lettuce_8792

Na versão dos Portishead


Pantaruxada

Nine Inch Nails - Hurt Bats for Lashes - Laura


jpowell180

Johnny Cash‘s cover of Hurt is especially hard-hitting!


Dragonfan_1962

The Band Played Waltzing Matilda - Eric Bogle (covered brilliantly by the Pogues) "So they gathered the crippled, the wounded, the maimed And they shipped us back home to Australia The legless, the armless, the blind, the insane Those proud wounded heroes of Suvla And as our ship pulled into Circular Quay I looked at the place where me legs used to be And thanked Christ there was nobody waiting for me To grieve, to mourn, and to pity But the band played Waltzing Matilda As they carried us down the gangway But nobody cheered, they just stood and stared Then they turned all their faces away"


ikesbutt

Puff the magic dragon lived by the sea........


Frogs4

If it helps, I have the children's picture book based on the song and the last page shows the grown up boy bringing his child to meet the dragon.


momonomino

It does help, I love this.


BennyTX

Thanks, still crying, but it's a little better


gwaydms

I'll remember this the next time I hear it. The real version!


sptfire

Oh my God thank you, that song tore me up as a kid. It's kind of like that book with the apple tree. We were so f*cked up as children. 


umthondoomkhlulu

I have a photo with me about 2 years old sitting on my dad’s lap as he played this on piano and sang so loud. Lost him in 2020. Crying now. Fuck it’s a sad, sad song


Millerdjone

My condolences, stranger.


umthondoomkhlulu

❤️


momonomino

I tried singing it to my kid once. I got a verse in and just started weeping.


DarthNarcissa

Why is that song so fucking sad? I had it on a Fisher Price record as a kid and would just start bawling whenever I heard it. As an adult, I tried to tell myself that it was just a hippie song about weed, but there's no way a song about weed would be that sad. Peter, Paul, and Mary were on to something with that song.


superstaticgirl

Argh! **


ikesbutt

I'm almost 70 and it still makes me cry.


fuggerdug

Jebus Christmas I'd forgotten that song *sobs uncontrollably*


Miserable_Bus2442

One more light - Linkin Park RIP Chester


Strong0toLight1

Nick Cave & the Bad Seeds- I Need You


SordidSplendor

Real Death by Mount Eerie


SaltySaltySultan

This is the answer, if you want to instantly feel sad just listen to this. I for one have listened to it a couple times and probably won’t ever again, too real


taco__night

I bought the vinyl after my brother died. Listened to it once, cried a lot.... Can't come to listen to it again. 5/5 amazing album, but please never come up on random shuffle.


_GETTER_

That album tore me apart. Its rare that emotion is conveyed so raw and real through music like that, you can *feel* the pain in every word.


HiveFiDesigns

Let me in - R.E.M. Mad World - Gary Jules version As Hope and promise fade - Chris Cornell One More Suicide - Marcy Playground Flow - Transister


Smarkysmarkwahlberg

La Dispute - I See Everything 


soggypizza

Most every song on Wildlife would qualify!


Smarkysmarkwahlberg

King Park is incredibly upsetting.


KFCmashedtaters

January 19- we buried our son today. Our youngest child That song destroys me


SWLucidWaker

Nine inch nails - something I can never have (still version)


pepperonipodesta

That entire album is incredible. And All That Could Have Been & Leaving Hope are really emotional too, and The Becoming is such a cool take on the track.


jdavidmcgregor

Hurt - Johnny Cash (particularly when paired with the music video) Seasons in the Sun - Terry Jacks In the Living Years - Mike and the Mechanics Strange Fruit - Nina Simone


sptfire

Yeah Johnny's remake of Hurt, oof. Hits 


Mylsmylsmyls

Strange fruit - Nina Simone


chinstrap

Townes van Zandt, "Marie"; most of the songs suggested here are not even close to it for sadness


GingeAndJuice

Ctrl+F to find "Marie" and happy to see it listed already. Jfc that song rips my heart out through my guts and holds it up for me to ponder. Pure hopeless ache, pure Townes.


w-izzy

Radiohead - true love waits


noahsmybro

She’s Leaving Home - Beatles


GoldenPoncho812

Bye Bye 👋


debaser64

Mount Eerie - [Real Death](https://youtu.be/-1UyUsz0A-A?si=s9qUeXhiMzZ6yYNi) and the rest of A Crow Looked at Me. Sufjan Stevens has a few too, [Casimir Pulaski Day](https://youtu.be/TfEkDqP34xo?si=yeVB0-O4LYGbGOWG) and [4th of July](https://youtu.be/JTeKpWp8Psw?si=XZunzjlnuvKA8zoA) to start with.


Erazzphoto

Pearl Jam’s remake of Last Kiss, absolutely heartbreaking


rustys_shackled_ford

I absolutely love this song.


Dreadzone666

My Dying Bride - Two Winters Only Woods Of Ypres - Finality Portishead - Roads I'd also add Lifelover - Mental Central Dialog, though it is a little harder listening to than the other three


justablueballoon

Roads!!!


Calmak_

With the context of what happened, the whole fifth Woods of Ypres album. Good pick!


chunky_bruister

It makes no difference-the band


csanyk

Gordon Lightfoot, If You Could Read My Mind.


[deleted]

Same Old Lang Syne by Dan Fogelberg. Waterfalls every time.


momonomino

Cancer - My Chemical Romance


Silverbitta

Brick by Ben Folds Five


JoyousDiversion2

Distant Sky by Nick Cave and The Bad Seeds can bring me to tears


[deleted]

The Last Song - Elton John Nutshell - Alice in Chains Wreck of the Edmund Fitzgerald - G.Lightfoot Say Hello to Heaven- Temple of the Dog


majesticgoldblum

Jonny Cash's cover of NiN's Hurt, BUT watch the music video. All the images of Jonny and June in their younger years and the present day, gets me everytime


liltooclinical

Damn straight.


dickysunset

Tears in heaven. Song about a son dying. Does not get anymore sad


MeInMyOwnWords

The only sadder thing than having a son die is being the person who is the sole reason for his death. Eric Clapton is and always has been an absolute moron. Great musician though.


GrouchyBunny

Tears in heaven, is pretty sad.


CottonTop3

Dust in the Wind - Kansas


RealSunglassesGuy

Atmosphere or New Dawn Fades by Joy Division


TheChineseChicken40

Fake Plastic Trees


Squirefromtheshire

What Sarah Said - Death Cab for Cutie


Mmzoso

Father of Mine- Everclear


Lunamoonbeam2011

Bright eyes 😭


Gloomy_Evergreen

The Night We Met - Lord Huron


yourmoms3rdhusband

Broadripple is Burning - Margot and the Nuclear So & So’s Mother I Sober - Kendrick Lamar Not the Same Anymore - The Strokes


SirBung

Luther Vandross - Dance with my Father


SaMSUoM

”The Eternal” and ”Decades” by Joy Division


ChanceSet6152

Apparently everyone is thinking text? Samuel Barber - Adagio for Strings


myriad00

To Forgive - Smashing Pumpkins This one hits me just as hard as Nutshell imo


[deleted]

'Song to the Siren' by this Mortal Coil and 'Can't Go Back' by Rosie Golan I can't listen to either.


MagaretSelf

Let Her Go - Passenger


ultraluxe6330

Do Ri Mi by Kurt Cobain (Considering the you know what) River of Deceit by Mad Season Unlovable by The Smiths


AWizardofEarthSea

Love Hurts- Heart/Nazareth


jacobt478

Famous blue raincoat - Leonard Cohen; The raven that refused to sing - Steven Wilson


lucmwis

Tears in Heaven by Clapton, nothing comes close.


kballs

Gary Jules version of Mad World gets me every time. As for modern, Noah Kahan - call your mom is pretty fuckin sad.


[deleted]

Pearl Jam - Yellow Ledbetter


DeboseChief

A song for you by Leon Russel is very depressing and gets me emotional. I believe he was writing this song for his wife when he thought he was dying. Goodbye my lover- James Blunt. When she loved me- Sarah Mclachlan. This is more of a situation I was going through-emotional based one. The scene in Toy story 2 where Jesse talks about her owner abandoning her resonates with me and my mom’s relationship.


Drew_Lorenzo_zzz

Keaton Henson - You.


Johnny_Minoxidil

Don’t take the girl - Tim McGraw Pretty Angry - Blues Traveler


Ananta_Govinda

Early Sunsets over Monroeville - My Chemical Romance


Ti_Fatality

Brand New - Limousine  My Chemical Romance - Cancer Frightened Rabbit - Floating in the Forth Pearl Jam - Last Goodbye


SouthOfHeaven663

Lorna shore: pain remains, specifically part 1


swurvegp

Rearview mirror -Pearl Jam


loondawg

Fire and Rain – James Taylor


ColdKwok

When I was in sixth grade one of our classmates died in a car wreck. For his memorial they had us learn & perform this song for him. I can handle it now, but for many years just could not. Like…at all.


Key-Scholar-2083

“Red Dirt Girl” - Emmylou Harris


[deleted]

[The Moubtain Goats - Deuteronomy 2:10](https://m.youtube.com/watch?v=oBprRgjmw3Q) It’s a song sung from the perspective of the last individual of their respective species before going totally extinct. The Tasmanian tiger, the dodo, and a Costa Rican tree frog.


Seebeeeseh

Some Devil by Dave Mathews


LeonGwinnett

Holding back the years - simply red


outofdate70shouse

Terrible Things - Mayday Parade


superstaticgirl

'After the Goldrush' by Neil Young gets me every time. 'Baby Mine' from Dumbo as interpreted by many artists including Bonnie Raitt. 'When Ye Go Away' by the Waterboys...


woodsoffeels

Something I can never have - NIN Silver - Woods of Ypres Alternate Ending - Woods of Ypres Finality - Woods of Ypres


erisedeye

Please, please, please let me get what I want - The Dream Academy version Forever Young - Alphaville


RaggedDawn

Hanging on a Star - Nick Drake


Zintack

Slint - Washer one of the most melancholy tracks I've ever heard


possy11

At 17 - Janis Ian


ShadowFlux85

Passenger - Let her go


Mrfixit729

Real Death - Mount Eerie 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 I 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 is bottomless and real It's dumb And I don't want to learn anything from this I love you


Confident-Practice-4

Keep me in your heart for a while. Warren Zevon


reduff

I love that Buckley song. He Stopped Loving Her Today by George Jones.


BombSniffinDog

He Stopped Loving Her Today George Jones


aimhelix

Libertines - I no longer hear the music Birdy and rhoades - let it all go


billjv

Gardenia - Mandy Moore


Elegant_Spot_3486

Goodbye by Air Supply


oreiner

Blank Page - The Smashing Pumpkins Somehow The Wonder of life prevails - Mark Kozelek & Jimmy LaValle Duet for ghosts (instrumental) - Ed Harcourt


myfriendjoel

Betty - Hot Mulligan


Abhir-86

Dave Thomas junior - I can't make you love me. Phosphorescent - song for zula.


SativasaurusRex

High Water by Bishop Briggs. She lost her sister to cancer and wrote that song. She released it just a few weeks before we lost my Dad to cancer. I can't make it through the whole song without sobbing.


budapen

Black and Blue - Louis Armstrong I 2ish I knew how it would feel to be free - Nina Simone


Miserable_Race6751

In hindsight, Rehab by Amy Winehouse makes me really sad when I hear it 


tangcameo

The Cat Carol - Meryn Cadell


amandamaniac

Smahccked my head awf by hot mulligan. Really powerful lyrics if you’ve ever lost someone to dementia, it’s about his grandma.


LastLapPodcast

Lullaby by Low


WishieWashie12

If you are a fan of Hitchhikers Guide to the galaxy, listen to the song Marvin I love you.


liltooclinical

*Scars* \- Papa Roach The people in my life that this song applies to is far too many.


Most_Committee1000

A Song For You - Reprise it's like Karen singing her last song to the world. Hauntingly beautiful.


Renton_Knox

The Micheal Andrews version of "Mad World".


HowBoutAFandango

Where’ve You Been - Kathy Mattea


strongbob25

The Saddest Song by Morphine is objectively the saddest song because it is called “The Saddest Song”


kev_mcallister

Borrowed Tune - Neil Young


da_benster

Routine by Steven Wilson


rustys_shackled_ford

[flirted with you all my life](https://youtu.be/96-flxOd_3w?si=YdZqP7eUMAs-HzRh) Also [first day of my life](https://youtu.be/xUBYzpCNQ1I?si=92CSupiizBM1bfcD) Both these songs make me tear up for exactly opposite reasons.


ThrottleAway

[Symphony No. 3, Op. 36, "Symfonia piesni zalosnych" (Symphony of Sorrowful Songs) - Henryk Górecki](https://www.youtube.com/watch?v=dEgCQhgkE6w)


[deleted]

•I can’t give everything away - David Bowie (his last song before he passed) •A Quick One before the eternal worm devours Connecticut - Have A Nice Life •Sea Swallow Me - Cocteau Twins


radio_esthesia

babe im gonna leave you joan baez


sevenwheel

Angel From Montgomery by John Prine.


Ciordad

Miss Otis Regrets - Ella Fitzgerald


notinsai

Like Suicide - Soundgarden. Last kiss - Pearl Jam. Black - Pearl Jam.


Trust_No_Won

Fiddlers Green - the Tragically Hip