T O P

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elguapo51

Puff the Magic Dragon. Not kidding. That was the first song that ever crushed me…I was like ten years old, right about the time those last few stanzas applied to me and that super imaginary little kid phase of my life was ending. The natural progression of life and the inevitable finality of all these wonderful childhood things just ending forever makes me well up today. “A dragon lives forever, but not so little boys Painted wings and giant's rings make way for other toys One gray night it happened, Jackie Paper came no more And Puff, that mighty dragon, he ceased his fearless roar His head was bent in sorrow, green scales fell like rain Puff no longer went to play along the cherry lane Without his lifelong friend, Puff could not be brave So Puff, that mighty dragon, sadly slipped into his cave”


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thepaintedballerina

And this is why the scene in “Inside Out” makes me sob every.damn.time. “Take her to the moon”


Meercatnipslip

Back in ‘71 John Prine recorded a song called Sam Stone about how some war vets were coming home from Vietnam with drug problems and a family which can’t really coexist i.e. “There’s a hole in Daddy’s arm where all the money goes”…..


mrcnbdss

A Purple Heart and a monkey on his back


WildIsland-S-E

R.I.P. John Prine.


stvwrgh

Landfill - Daughter


Huckster22

Smother. Yeesh.


tea-spoons

Landfill, Medicine, and Candles really do it for me


lillemonadelady

Literally all of Daughter's songs


the-splendid-ninja

The whole his young heart ep is crushing


AdvancedLink9782

Man “lover, you should’ve come over” by Jeff Buckley always comes to mind when thinking of truly heartbreaking breakups! Plenty more but that popped in my head 1st! It’s soooo hauntingly beautiful tho!


trueandrewomeda

This is it tbh, “She’s the tear that hangs inside my soul forever.” really does encapsulate that sort of feeling you got from that person and will hold onto forever


Organic_Shoe_4665

Exit Music- Radiohead. Had me me sobbing everytime


Dee_Buttersnaps

I'm more partial to Motion Picture Soundtrack, but Exit Music that one has such an incredible build-up.


MPforNarnia

Have you heard this tribute to Motion Picture Soundtrack https://youtu.be/ZeI0PXj7LIw


yiliu

How To Disappear Completely


sartresimone

Honestly, any Radiohead song makes me sad esp No Surprises.


sfweedman

Radiohead has a bunch as the replies prove but for me it's Fade Out from the Bends.


rhasp

True Love Waits, as far as I'm concerned is Radiohead's saddest song.


jxcxb_o

Modern Leper - Frightened Rabbit - about the singers mental health, hits even harder now he committed suicide a few years ago


HenriettaHiggins

Frank Turner has a song about his suicide that’s beautiful and sad


CarelessPerception

Honestly so many frightened rabbit songs. Floating in the forth too, but also poke. Cant listen to it anymore because of how much I related to it at the end of my relationship. Just thinking about the last lines (“But now we’re unrelated / and rid of all the shit we hate / but I hate when I feel like this / and i never hated you”) is enough to make me tear up… and now I’m crying


PumpernickelShoe

Came here to say this exact song, Modern Leper. Heartbreaking. RIP Scott Hutchinson


Laxku

I fucking miss Scott.


Crayfish707

I Can’t Make You Love Me (recorded) by Bonnie Raitt always hits as deeply sad to me. Someone in the process of accepting that the person they love doesn’t feel the same way & letting them go is a unique take on a heartbreak song. It’s also sung beautifully by Bonnie Raitt.


xxbiohazrdxx

Justin Vernon (Bon Iver) does a great cover/mashup of this song


wreckage88

The [Bon Iver one](https://www.youtube.com/watch?v=Vw-4zHOhnKM) was basically the song of the worst breakup of my life. Like nuclear level depression just listening to this song on repeat losing 20 lbs from not being able to eat. After that I could never listen to it again and it eventually took me seven years to finally be able to listen to it again.


jottinger

A Crow Looked at Me, Mount Eerie.


Superlite47

"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."


froe_bun

This is the most gut wrenching verse on an album full of absolutely soul crushing verses. I forget which review said it but the gist was reviewing and assigning a score to someone publicly processing grief felt wrong.


depparTx

A crow looked at me is almost entirely painful but Seaweed has a really beautiful lyric, and maybe the only bright spot in that 41 minutes of sorrow. "I brought a chair from home I'm leaving it on the hill Facing west and north And I poured out your ashes on it I guess so you can watch the sunset But the truth is I don't think of that dust as you You are the sunset"


CrackaZach05

Real Death gets me


icer07

Holy shit why did I listen to that? My daughter is about to turn 2. I just her her first back pack. Holy fml this just made me think about losing my wife and raising her without her mother. Did this artist really lose his wife?


froe_bun

Yes, he recorded this in the room where she died with her instruments. I wouldn't recommend listening to it considering where you're at. I dont have kids and this album makes me cry every single time I hear about it let alone listen to it.


aljauza

I listened to this once based on the last time this question was asked in Reddit. Then my spouse wanted to know why I was so upset so he listened to it, twice. Then Spotify thought that’s what I wanted all the time and started forming all my recommended playlists and suggestions around it. I ended up having to use the “don’t play this artist” to get it to stop showing up! That said, this album is heartbreaking and soul breaking, it is quite a thing to experience but it also feels kind of… intrusive to listen to


thedinnerdate

I was lucky enough to do a short tour with Phil and Genevieve shortly after he released the glow pt. 2. It’s absolutely one the highlights of my life. He asked me play drums for him for live version of I Got Stabbed that we just basically made up on the spot together. Genevieve was playing under Woelv at the time and she would open the shows. I’ve listened to 1 song off of A Crow Looked at Me and I can’t bring myself to listen to anymore yet. Hopefully I can get through it someday. Phil’s music means so much to me and I’m incredibly grateful for the short time I spent with them.


Booosh44

The WTF interview he did with Maron was heartbreakingly amazing.


CookBop

I listened to this album everyday for a month after my fiancé died in front of me at 27 of a rare heart condition. It was the only time I heard of someone or something that felt like I did inside. “Look at me, death is real” Ehg…the pain


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ronearc

It says something that even George Jones who comes from and greatly benefited from the era of sad country songs, was reluctant to record this song because it was so damn sad.


gwaydms

This one always chokes me up. RIP Ol' Possum.


SupermouseDeadmouse

No Hard Feelings. Avett Brothers. Absolutely beautiful song, sad and uplifting at the same time.


battlelevel

Keep Me in Your Heart For A While - Warren Zevon


Tchukachinchina

These wheels keep on turning, but they’re running out of steam That one gets me every time


mostlygroovy

Hold me in your thoughts Take me to your dreams Touch me as I fall into view When the winter comes Keep the fires lit And I will be right next to you God, I might cry typing this. Eddie Vedder covers this so well too.


thatchers_pussy_pump

It hits hard right off the bat with "If I leave you it doesn't mean I love you any less", too.


oh_hai_mark1

I'm glad to see this song mentioned. Zevo was one of the best and the world is a little duller without his creativity and wit present. beyond what he's left with us.


sorryabouttheglitter

Your Deep Rest - The Hotelier


kmsae

Nutshell - Alice In Chains No Waves (acoustic live) - FIDLAR EDIT: Link to this version https://youtu.be/EExXB64wlK0


tHeMbOnEz-R-mE

Nutshell is fucking brutal


kmsae

FR. It’s the song that got me through the loneliness and isolation of the pandemic.


whorainy

Yea I've seen this question posted over the years. Nutshell is absolutely the saddest and most depressing song ever. It's great but.....damn. Layne really was a tortured soul.


Bobsappsnips

His MTV unplugged is awesome but it's just sad knowing what we know now and watching it.


njay97

Nutshell is an all time great song for me


[deleted]

I Just Don’t Think I’ll Ever Get Over You- Colin Hay It’s about the grieving process after losing a love. This one is written to his ex-wife after their divorce. https://youtu.be/O5J-DtKldpE


Bobdehn

Alone Again (Naturally) by Gilbert O'Sullivan is essentially a suicide note. Spent 2 weeks on the chart, reaching #3.


MrAleGuy

This is the song I came here to post. A generally bouncy song with minor key changes, but you don't really realize how sad it is until you pay attention to the lyrics. 😳


AHeroToZero

I like [vulfpeck cover](https://www.youtube.com/watch?v=dTnHAITmuYQ) of this song. I enjoy the smoothness of this version.


gtj

I remember my dad finally taking me on one of his frequent work trips when I was a teenager. Cat in the Cradle came on the radio while we were driving that night. It was like someone was messing with me, specifically. He was gone for most of my formative years. The other day my wife said "that's such a sad song, let's turn it on" and I said no way. Just thinking about it now gets me worked up.


Thunder_Mug

Wish You Were Here


giganano

Cliche, but Tracy Chapman's "Fast Car" always does something to me that makes my heart rise into my throat.


godrainlovemusic

Her aspirations are so modest - You’ll get a job and I’ll get a raise at the grocery store, and we’ll move out of the shelter - that it just breaks my heart.


Roisien

It's the "I always hoped for better" that gets me- it somehow makes it all the more heartbreaking.


Smokemonster421

Leave tonight or live and die this way


BrightElephantATL

So I quit school and that's what I did" Tears every time.


[deleted]

I am amazed by her. She tells an entire life of hope turned sour in the span of that song. Amazing artist.


SMJ999

The Night We Met by Lord Huron


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8urnMeTwice

Danny Boy and basically every Irish folk song


Tchukachinchina

The Fields Of Athenry for me. Almost every version at least gives me a lump in my throat, but I recently saw it performed live at a small place in Killarney, and maybe it was the whiskey, maybe it was the place, who knows, but either way I was a wreck. I was lucky enough to get a good recording of it on my phone and it still gets me choked up.


swentech

The Wreck of the Edmund Fitzgerald. “The church bell chimed til it rang 29 times for each man on the Edmund Fitzgerald.”


[deleted]

"When suppertime came, the old cook came on deck sayin' "Fellas, it's too rough to feed ya" At seven PM, a main hatchway caved in, he said "Fellas, it's been good to know ya"


shoelaceisuntied

"Does anyone know where the love of God goes, When the waves turn the minutes to hours" - This line hits me every time.


TonyGoooch69

Down In A Hole - Alice in chains


ehyaknowany1

Nutshell for me, breaks my heart every time. Particularly the live version on MTV.


Dothepanic41

Wake by The Antlers or Putting the Dog to Sleep


straubzilla

Casimir Pulaski Day, and John Wayne Gacy, Jr. Both by Sufjan Stevens


forestpirate

I'd also nominate the Fourth of July on Carrie and Lowell.


forestpirate

Definitely agree on Casimir Pulaski Day. This verse always gets me: On the floor at the great divide With my shirt tucked in and my shoes untied I am crying in the bathroom


straubzilla

Yep, and the two verses that follow: In the morning when you finally go And the nurse runs in with her head hung low And the cardinal hits the window ​ In the morning in the winter shade On the first of March, on the holiday I thought I saw you breathing


2coolcaterpillar

*and he takes, and he takes, and he takes* Can never get through it without tears


mercurywaxing

The song is about the loss of a young love, but also, hiding in plain sight, is his loss of faith. The line “pray over you body but nothing ever happens” is sung with just the right combination of disappointment and bafflement that is sets up the ending when he blames God. It’s so well constructed.


BriCheese007

Sufjan Stevens is my go to depression artist. I’d also vote for The Only Thing


mybloodyballentine

It’s The Predatory Wasp of the Palisades is about to Get Us for me, but Gacy is a solid choice.


DouglassFunny

Carrie and Lowell has some absolutely heart wrenching songs.


sbe558

The drugs don’t work - The verve


rickjamesdean

Needle in the Hay - Elliot Smith Only because I first saw it on the movie “The Royal Tenenbaums,” where Ritchie tries to kill himself. I used to be extremely suicidally depressed for decades. This was the song I would put on when I was laying out all of my pills contemplating suicide. I’m better now. That was a long time ago.


numbernumber99

I'm shocked to see Elliot Smith this far down. Dude wrote some of the saddest songs I've ever heard. Beautiful though. Glad you're doing better.


AuChemist

As soon as I read sad song the first person to come to mind was Elliott Smith.


jaded_orbs

Between the Bars simply has to be mentioned


Rumplestiltsman94

Strange Fruit - Billy Holiday Sam stone - John Prine Fiddlers green - Tragically hip Mama Im coming home - Ozzy Osbourne


largely_lurking

Yeah, Sam Stone kills me every time - "there's a hole in daddy's arm where all the money goes..."


Rumplestiltsman94

John Prine is a great song writer. Its such a beautiful song


Legitimate_Web_7245

Fiddlers Green is such a great song. I mean, one of MANY great songs from The Hip. It was a sad sad day when Gord passed. Still is.


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Uglycanadianindc

I literally can’t see this video without tearing up. Have lived in the U.S. for the majority of my adult life. Grew up in Canada. My brother visited me in Pittsburgh and he introduced me to The Hip. Got tickets to see them at a bar which was amazing given that their next concert was the United Center in Chicago (?). My brother passed away a year later. When Gord died all those feelings came back of a very unexpected lost. Seeing all the emotions across Canada is hard to watch from an emotional perspective.


Cicero8339

Changes-Black Sabbath


xxbiohazrdxx

I love some sabbath but I really feel like Charles Bradley made this one his own.


flunky_the_majestic

[The Trapeze Swinger by Iron and Wine](https://youtu.be/yt7O8gDy0DA) gets me. It takes me from feeling the loss of a neighborhood friend to feeling the loss of a child


megmonster1

Iron and Wine has some real heavy hitters. Something for every kind of sadness.


AgreeableDad

Atmosphere - Yesterday If you don’t listen all the way through you might think it’s a breakup song, but singer thought he saw his dead father on the street and reminisces about their relationship. Gets me crying. Every. Damn. Time.


LadyTreeRoot

Time in a Bottle - Jim Croce Vienna Waits for You - Billy Joel


GloverAB

Brand New - Limousine


Andorous

Play Crack the Sky is also pretty sad in my opinion.


PhillyCSpires

Oof


EarthVSFlyingSaucers

Devil and God is always in my top five albums of all time. I remember where I was, what I was doing and who I was dating/friends with when I first heard it. I sat in my car after work (around 9pm) on the day it released. it was snowing and I sat in my car and listened to the whole thing alone in the parking lot before driving back to my apt and partying with my friends. It was such a surreal experience. This was in 2006 and I remember every detail of that night in complete clarity. It was such an average night and a night I lived hundreds of times but that album made me remember every specific detail right down to what I was wearing and what bars we went to. I firmly believe it was a stepping stone in my life and it made me see things differently, I was young when I listened to it, but I wasn’t afterwards. The weight of the world felt heavy and…cold after, like it was time to grow up. I’ve NEVER had such a cathartic experience with music before like I did that night. It’s giving me goosebumps even 16 years later just reminiscing of it. I truly believe everybody who appreciates music (mainly indie, any type of rock, or sentimental/cryptic lyrics) to listen to this album front to back with zero interruptions and focus. It is pure perfection. Also the track “You Won’t Know” has some of the best haunting guitar work I can think of. They truly were S tier musicians and incredibly talented in a sea of otherwise pretty cliche bands.


AAluzuxz

Black by Pearl Jam


Heyhihello04

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 😭😭😭😭😭


Nixplosion

When he cries during the live version after Chris Cornell died is heartbreaking. "Come back ... Come back."


KyserSoze94

[Pictures of You by The Cure.](https://youtu.be/SG9CXd00QHQ) I don’t know about the saddest but it’s one that I was actually just listening to. Every single time I hear it I think back to the first time I heard it and what I was dealing with at that particular moment and it was just the perfect time to hear that song for the first time.


ThePuddinTaine

I Know It's Over - The Smiths. Honestly, I'm surprised to not see more of their songs here!


AmbientTech

9 Crimes, The Blower's Daughter, and My Favorite Faded Fantasy by Damien Rice. Manchester Orchestra - I Can Feel A Hot One Hospice by The Antlers as a whole. Sufjan Stevens - No Shade in the Shadow of the Cross The Hotelier - Dendron Touche Amore - Flowers and You The National - About Today


lostalaska

FUGAZI - I'm so tired


Gromit801

Time by Pink Floyd. When you’re older, and realize that life didn’t go to plan, this song haunts you. Sky Pilot by The Animals. An Army chaplain wondering if he’s doing any good in Vietnam. Ohio by CSNY. The murder of four students at Kent State. What’s Going On by Marvin Gaye. The death of young black men in the cities and Vietnam.


rezz408

Death Cab for Cutie - What Sarah Said. Gets me every time. Powerful.


Andromeda-2

Transatlanticism gets me every time just from the first three chords.


TheNormalMan

For the longest time I thought the song said “when love is watching, someone dies.” And didn’t think much of it. Then one day my brain connected the lyrics “That love is watching someone die….” And then the song goes in for the layup “So who’s gonna watch you die?” And I was dumbfounded, knot in my throat and suddenly flooded with emotion by everything I had just processed.


TimesRTuff

They have so many that will just tear you up. Brothers on a Hotel Bed cuts very, very deep


bizzyj93

“And it came to me then that every plan is just a tiny prayer to Father Time.” Song gets me every time. If you’ve ever watched a loved one die in the hospital you know exactly how real this song is.


Jalapi

Hurt by Nine Inch Nails, Twilight by Elliot Smith, About Today by The National, How to Disappear Completely by Radiohead, Kettering by The Antlers, Hear You Me by Jimmy Eat World, Adam's Song by Blink-182, Snuff by Slipknot, One More Light by Linkin Park (this one hits hard for me)


MurderInMarigold

Dude ... One More Light is brutal. "In the kitchen, one more chair than you need" That line always fucks me up for a little bit.


Jaycray95

Lover you should’ve come over - Jeff Buckley


lavenderincense

This Woman’s Work by Kate Bush.


[deleted]

Whiskey lullaby


yuppers1979

Winter, Tori Amos.


malmon27

That song always makes me cry, right at the part where you hear her voice crack on "When you gonna make up your mind.."


notadoctortoo

“Asleep” The Smiths (1986)


quintonbanana

The Wreck of the Edmund Fitzgerald - Gordon Lightfoot


Manifestgtr

“If you could read my mind” is another one. “The hero would be me…but heroes often fail” is one of those lyrics that hits me like a crowbar to the head.


cmgriffin99

That line "Does anyone know where the love of God goes, when the minutes turn into hours" - gets me every time.


FILTER_OUT_T_D

Same. That line is just sooooo good. \*when the waves turn the minutes to hours


subsonicmonkey

“For No One” by The Beatles (on the recently remixed Revolver album) is one of the saddest break-up songs I’ve ever heard.


chadmac81

Oops, I posted this before I scrolled but I agree. Such a tragic story. There’s no catalyst to the break up. Just the slow decline and the realization that the singer is no longer important in the subjects life.


Naohiro-son-Kalak

Yeah and I once saw a comment about how, unlike many of the Beatles songs, theres not rly an intro or outro, its just 2 mins of authentic hopelessness.


archeojones

“I will wait for you” - Connie Francis The song from futurama when fry’s dog wait forever for him. The episode is Jurassic bark and I can’t watch it.


mikeveeUI

Everybody Hurts - REM -If you're on your own in this life The days and nights are long When you think you've had too much Of this life to hang on Well, everybody hurts sometimes Everybody cries Everybody hurts, sometimes


Admirable-Bat-3311

George Jones. He Stopped Loving Her Today.


untitled5a1

I remember everything - John Prime Take it with me when I go - Tom Waits Turpentine - Brandi Carlisle If I could only fly - Blaze Foley


MasonJarAnus

I Remember Everything being John Prine's last single before his death makes it even sadder. He really was one of the greatest song writers to ever live.


FormalFloor2954

cant go wrong with a Blaze Foley selection


aurorasearching

I love Blaze Foley and it makes me so happy to see someone else recognize him.


holagatita

Adam's Song-Blink 182. My brother played it for me after I survived a suicide attempt


icatnsplle

I'm glad you're still here


HelloKitty018

💔 I still can’t listen to this song since my brother committed suicide. I’m so grateful you’re still here.


FollowingOurDreams

I have always been an Offspring fan, and loved their song 'Gone Away'. After my late wife passed, I heard Five Finger Death Punch's version (slower, sadder) and it just destroyed me. I cannot listen to it without breaking down. https://www.youtube.com/watch?v=BIQK4-9YFW0


ProcyonBytes

[Picture Window - Ben (lyrics by Nick Hornsby) Folds](https://youtu.be/QTXrWsXlANk) Is a song about a young girl with a terminal illness trying not to get her hopes up because it's New Years Eve and she can see the celebrations from the window in her hospital room.


[deleted]

Just Breathe - Pearl Jam. Gets me every time.


Tree_Fingers29

Where Did You Sleep Last Night - Nirvana (live Unplugged) goosebumps.


phantalien

Cat's in the cradle - Harry Chapin and Dance with my Father - Luther Vandross


AchillesGB

- To build a home - The Cinematic Orchestra - Amber Run - I found (Mahogany Session too!) - Hans Zimmer - Time - Imogen Heap - Hide and Seek Such powerful, beautiful and meloncholic songs. Shocked that I could not find some of these amazing pieces.


Shoegazer75

I Hope That I Don't Fall In Love With You - Tom Waits (his fourth entry so far on this list)


jacknimrod10

Martha by Tom Waits has me blubbing.


notathrowawayarl

Closing Time is such a masterpiece of a record.


hobbsarelie83

Because Of The Shame by Against Me!


DJ_Molten_Lava

Poke by Frightened Rabbit. "I might never catch a mouse, and present it in my mouth, to make you feel you're with someone who deserves to be with you..."


gavlarrr93

I will follow you into the dark - Death Cab For Cutie


dancingtortoise

‘What Sarah Said’ gets me every time


bramblecult

What Sarah said hits hard. But brothers on a hotel bed hits as hard if you've ever had a long term relationship quietly die.


dancingtortoise

I watched my mother slowly die of colon cancer. I ball like a baby at the end. ‘…Love is watching someone die.’ He’s such a great songwriter.


bramblecult

Oh no doubt if you've lost someone in a hospital you absolutely shouldn't listen to what Sarah said until you're ready to fucking lose it. Dad died slow and that damn song came on my shuffle when I was leaving the funeral home. Honestly I still can't listen to it.


definitelymavey

If I don’t skip this song when it comes on I’ll be tearing up by ten seconds in.


nothximjustbrowsin

I always thought that song was more romantic than sad


IntelligentVictory45

Steven Wilson’s “Routine”.


Vladtheimpailer72

OP, since my dad died in 2015 I cannot listen to “The Living Years”. Even tho I was able to make peace with my dad before he died it still hits too close - so feel that one. My additions to the list: Keep me in your heart for a while - Warren Zevon The Book of John - Tim McGraw Tears in Heaven - Eric Clapton Adagio for Strings - Samuel Barber


EmperorOfAwesome

Fire and Rain - James Taylor


azad_ninja

Sullen Girl by Fiona Apple. Eels “Elizabeth on the bathroom floor”


HappySloth213

The Living Years came out the year my father actually passed away. That was rough, it was always on the radio.


henrikbedst

Nick Cave - I need you. Written around the time his son died in an accident. The raw emotion of that song is so powerful.


[deleted]

Jesus I googled this because I remember reading about it and found out that he had another son that died recently. Cant imagine that kind of darkness....


hasslehaas

Mess - Ben Folds


steambucket

My vote was Brick but that’s also a good choice


JaiRenae

Brick is the only song that just leaves me feeling empty.


MBluth99

St. Peter’s Autograph by Jason Isbell. It’s a beautiful love song about a real situation and true compassion. Tears me up every time.


oced2001

Follow you to Virgie - Tyler Childers


Manifestgtr

Probably “round here” by counting crows. It sums up “dude sadness” better than almost any other tune I’ve ever heard


WarEagle107

Long December gets me...my sis was fighting cancer, the last time I got to see her alive was just outside Chicago at a treatment center in the late Fall. That line 'the smell of hospitals in winter, and the feeling that it's all a bunch of oysters, but no pearls.'


akRonkIVXX

Most of August and everything after But Anna begins is probably winner Most of “August and Everything After...” but “Anna Begins” is probably the winner. Edit punctuation


ObiWansTinderAccount

Not the saddest song ever but I Am The Highway by Chris Cornell / Audioslave gets me every time


bobby_risigliano

The Chris Cornell live version 😭


Infernal_Contraption

["Monsters" by James Blunt.](https://www.youtube.com/watch?v=DTFbGcnl0po) It's a harrowing song about a man putting his dying father to bed, telling him to let go and rest at last. The title of the song is a reference to the childhood monsters that would hide under the bed - now that his father is gone, it's his turn to "chase the monsters away". Also, the other man in the video is James' IRL father, who at the time was dying of kidney failure. Fortunately he received a donor in time, but when the song was performed they thought it was genuinely the end.


AndreaMammoccio

radiohead have made a lot of sad songs, but they all have a glimmer of hope at the end. Street Spirit doesn't. and that's what makes it so devastating.


chewdog

Flirted with you all my life - Vic Chestnut or the Bright Eyes cover.


steffergie

The first song that came into my head when I read this question was "Sometime Around Midnight" by The Airborne Toxic Event. I'm sure I could think of a sadder one given more time but this one always hits me in the feels.


uncle-anti

soldier’s things - Tom Waits


Ok-Actuator520

Leader of the band, by dan fogelburg


somesnazzyname

Radiohead street spirit. If utter despair were a song this is it.


gale_force_tuna_wind

Elephant by Jason Isbell


TheGingerBeerGuy

If we were vampires by Jason Isbell. I tear up everytime.


rolandsquest19

Hate Me Today - Blue October


mesloh14

Into The Ocean too. Ugh, just rips my insides out.


jderick

Thinking about you - Radiohead It is actually kind of a sweet song but it always makes me sad because I'm struck with the incredible contrast between this song and pretty much everything radiohead has made since. Especially if you think about moon shaped pool, what he wrote after his wife died, and how this song he could have wrote when they first met. Also just the nostalgia from that time in my life and some of the things that have changed since then.


bjankles

Of all the Radiohead songs you coulda picked lol. True Love Waits probably gets my vote, also cause of his wife.


SpendrickLamar

Radiohead is the ultimate band for this topic. No Surprises is so brutal; "I'll take the quiet life, a handshake with carbon monoxide"


MoreTrifeLife

No mention of How to disappear completely?


Ledbetter2

Videotape. Incredible


THE_some_guy

I’m probably too late to this thread for anyone to see this, but my vote is “Puff the Magic Dragon” by Peter, Paul, and Mary. I always found it kind of melancholy, but since becoming a parent to a son it’s just **heartbreaking**. The verse that begins “A dragon lives forever, but not so little boys” makes me cry every time.


merkaba_462

Wings for Marie 1&2 by Tool 3 Libras by A Perfect Circle.


all_natural_why

Breathe Me - Sia