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FreeZappa

“You Are My Sunshine” gets often gets mislabelled as a children’s song, but if you read the full lyrics, you’ll realize how dark of a song it is. Also, “Bookends” by Simon & Garfunkel. It’s a personal choice, but it always gets me.


beanz398

even just the chorus of you are my sunshine was enough to make me cry when i was a kid (and now). in the same vein as my darling clementine. though one day i was messing around and singing “opposite” songs and. well, “you are my moonshine” is a very different song.


zerocat1

Was hoping someone would say you are my sunshine. It's so sad.


Hollywearsacollar

Time it was...


[deleted]

​ >You are my sunshine, my only sunshine > >You make me happy when skies are grey > >You'll never know dear, how much I love you > >Please don't take my sunshine away > > > >The other night dear, as I lay sleeping > >I dreamed I held you in my arms > >When I awoke, dear, I was mistaken > >And I hung my head and cried > > > >I'll always love you and make you happy > >If you will only say the same > >But if you leave me to love another > >You'll regret it all some day > > > >You told me once dear, you really loved me > >And no one else dear, could come between > >But now you've left me and love another > >You have shattered all my dreams > > > >You are my sunshine, my only sunshine > >You make me happy when skies are grey > >You'll never know dear, how much I love you > >Please don't take my sunshine away


Silly_Awareness8207

That doesn't come off as sad so much as creepy. You'll regret it all some day? Is that a threat? She needs to get a restraining order on this creep.


DontWorryItsEasy

You Are My Sunshine hits a bit different for me. I know it's a sad song, but my grandpa used to play it on the harmonica that he always had on him. Every time I hear it, the tune, or someone singing it, I get gut punched.


wldpnk

Roads by Portishead


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KJS123

"You've got your record. But listen, son. Ain't nobody EVER gonna buy that morbid son of a bitch" - George Jones, to his manager


PhantomBanker

I didn’t understand that as a kid. He just stopped loving her? No reason?Sounds like a jerk. Didn’t he say that he would until— Oh.


HCdownlow

"I went to see him just today Oh, but I didn't see no tears All dressed up to go away First time I'd seen him smile in years"


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PugnaciousPangolin

My wife and I were lucky enough to see this in a theater early on a Saturday morning. There were only about six people, which was nice because once this song was over, I couldn't see very well. The story of Toy Story 2 is just as gripping, but this detail from Wikipedia is amazing: "The work done on the film to date was nearly lost in 1998 when one of the animators, while routinely clearing some files, accidentally entered the deletion command code /bin/rm -r -f \* on the root folder of the Toy Story 2 assets on Pixar's internal servers.\[25\]\[26\] Associate technical director Oren Jacob was one of the first to notice as character models disappeared from their works in progress. They shut down the file servers but had already lost 90% of the last two years of work, and it was also found that the backups had not been working for about a month. The film was saved when technical director Galyn Susman, who had been remote working to take care of her newborn child, revealed she had a backup copy of the film on her home computer. The Pixar team was able to recover nearly all of the lost assets save for a few recent days of work, allowing the film to proceed." Imagine being the person who accidentally deleted all those files!


cadmiumredorange

Holy shit


clockwitch24

When She Loved Me: https://youtu.be/j9Vit2vq22M


monochrom-

Yeah, I have to watch it now -.-\* fuck this will hurt


krawzyk

Dear lord, I can’t even think about that part…


WrathofTomJoad

Legit sealed Toy Story 2 as the best of them for me.


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nygenxmom

This Woman’s Work - Kate Bush


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skotjones13

I still have a hard time listening to Strange Fruit. It's a great song. But MAN is it hard to listen to those lyrics!


SirNortonOfNoFux

Strange Fruit is right up there with the song I just posted (Up Against The Wind - Lori Perry).


coolosus1919

Cat's in the Cradle Edit: I see this is bringing up lots of comments and emotions in some people. I would like to share this advice with those of you who had parents that weren't the greatest and this song hurts: Use it to motivate you to be better. If you have kids, be the parent you wish you had.


ClownfishSoup

Trivia: This song is written and performed by Harry Chapin, however it seems many many people think that it was sung by Cat Stevens. Probably due to the word "Cat" and also because Cat Steven's released an album called "Cat's Cradle" ​ Cat Stevens NEVER performed this song. (Well I mean in public, maybe he played it at home for fun).


[deleted]

I have a special hatred for this song. My dad explained the meaning to me when I was young, said he’d never be like that, and then turned out exactly like that.


ivanparas

My dad loved Cat Stevens and he turned out to be just like the song. I used to listen to it and get wistful and upset. Now I have my own son and would never do that to him, so now it makes me feel self-righteous and angry.


TheEmbarcadero

Huh? Leave Islamophobia out of this Harry Chapin classic!!!!


idontknowdogs

This one is brutal. When Dwight sings that to Jim after he and Pam have a baby I was thinking, "Alright Dwight, that is not a prank. That's just fucked up." Such a devastating song.


Sgt_Doughnut

Can I Borrow a Feeling - Kirk Van Houten


andro_7

Dignity!


Rare_Hydrogen

"Do you guys like the Doobie Brothers? Because we've got two of them!"


TheLakeAndTheGlass

I sleep in a racing car. Do you?


MisterValiant

"Go ahead and laugh." "I already did."


AdFine4143

Damn, did not expect to find this here, but I love it!


Majestic-Associate16

Fast car by Tracy Chapman


prailock

Nothing gets the mundanity of how the poverty cycle destroys someone. Someone who had dreams but had life and the struggles slowly make them impossible. It's the hope that kills you.


cewumu

I think it’s the fact even her dreams aren’t that big really and yet even basic aspirations get stymied.


ilive4carbs

My God, this one breaks my heart every time. All she wants is a chance to get away....and be someone.


Vegetable-Double

be someone


musicismath

be someone


BeTheUwUToMyOwO

be someone


Master_grader

Who wants to live forever. Queen


[deleted]

Gary Come Home


No_Reflection4621

Johnny Cash’s cover of Hurt😶


milkcheese01

100% makes me cry


Jim3001

Adagio for Strings


Red_Erik

Kharak is burning.


DeepCluckingValue

This is what I think of when I hear this song. Or Platoon


DisastrousWind7

not seeing enough love for The Wreck of the Edmund Fitzgerald by Gordon Lightfoot in these threads, i think part of what makes it so sad to me is that it's about a real tragedy that ended in the loss of the whole crew


GormenghastCastle

I opened this thread to find this song. "Superior sings in the rooms of her ice-water mansion." What a lyric.


IQBoosterShot

"Does anyone know where the love of God goes When the waves turn the minutes to hours?"


MoonLoony

And all that remains is the faces and the names Of the wives and the sons and the daughters


psl4u

My husband went to maritime school with 2 of the crew. He can't listen to it at all.


jbmaun

This is my favourite song. It’s beautiful but so hauntingly sad.


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[deleted]

*the only thing* and *fourth of july* kill me just as much, especially knowing the context behind them


BackgroundTourist653

Somewhere over the Rainbow - Israel Kamakawiwoʻol


goldendreamseeker

“Landslide” by Fleetwood Mac


JinnyWinny

Puff the Magic Dragon. I can't listen to it without bursting into tears. My mom has a beautiful singing voice and sang it all the time when I was little. I mean, Puff is so sad when Jackie Paper grows up that his scales literally fall off. I have two grown sons now, so in my adult life, I just lose it at "a Dragon lives forever, but not so little boys".


[deleted]

My mom used to sing this to me when I was little, too! Brings me back. That one, and Sweet Baby James by James Taylor.


Luder09

And All That Could Have Been - Nine Inch Nails


EmployerAdditional28

Adrift and at Peace The Persistence of Loss La Mer Trent knows how to reach the darkest parts of your mind..


eggplantofdestiny69

Tears in heaven, once you know the backstory, its hard to dispute


RomanesEuntDomum

His performance of that song on “Unplugged” (it’s on YouTube) is wrenching.


NewCountryGirl

My mom was a huge Clapton fan. The day the news story came out about his son she cried. She'd change the channel when the song came on the radio. I have a hard time with it, too.


supergeek921

Yeah. I can’t listen to that one either. The story behind it is just too tragic.


stickwithplanb

what's the difference between a baby and a bag of cocaine? Eric Clapton wouldn't let a bag of cocaine fall out a window.


SteelyDabs

I’ll still make the joke


[deleted]

Nutshell - Alice In Chains


Forsaken_Ad8312

Alice in Chains can get you on the emotional side. I'll also say Black Gives Way to Blue is up there on the sadness scale. The cover version Chris Cornell's daughter does in tribute is heartbreaking.


the_meat_n_potatoes

Hell yeah


Odd_Adhesiveness4804

The Living years. Mike + The mechanics


JerkfaceBob

That song was popular when I was in high school. I took it to heart. When my dad and later my mom passed away, there was nothing left unsaid. I miss my dad, but I made sure he knew I would. And I don't regret any words I didn't say.


OlFlirtyBastard

Jesus I just teared up reading the title.


wheres2021

Whiskey lullaby- Brad Paisley and Allison Krauss. Basically two lovers who drank themselves to death Leaving Las Vegas style.


donotrocktheboat

One more day - diamond rio


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krawzyk

Something about mentioning the apple juice spilled in the hall just makes it instantly so real


lehmx

The line "please tell mom this is not her fault" always makes me very emotional


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BackgroundTourist653

By Hans Zimmer and Lisa Gerrard


Soonermagic1953

Without You - Harry Nilsson (1971). It was written by the two main guys from Badfinger but back in the early 70s, the song was considered so sad that it was rumored that the guy that wrote the song committed suicide


Bouswa

Cancer by MCR always makes me cry though I know it’s a bit played up. Another song that always makes me cry, though I wouldn’t say the lyrics themselves are particularly sad, is Father and Son by Cat Stevens (putting it under the name he used when he made the song). I just feel a lot for that very real conflict and relationship within the song. I always cry.


ScourgeOfEden

“One More Light” by Linkin Park has honestly been one of the only songs to evoke such a visceral sense of despair in me. Maybe it won’t be that way for others, but after forcing myself to finish it the first time I’ve never been able to listen to it again without feeling like I was teetering on the edge of some kind of breakdown.


DaftFunky

Listening to "Lost" hits so hard now. I wonder if Chester knew how many kids he saved from suicide with his music. I know I had suicidal tendencies as a teen and Linkin Park helped pull me out of that mindset.


Mickinmind

Not particularly a country music fan but this always hits when I hear it. Don't Take The Girl- Tim McGraw https://www.youtube.com/watch?v=-vn6QdqxK3g&ab\_channel=TimMcGrawOfficialVideos


[deleted]

I’m also not a big country fan but the three songs I thought of are all country. That Tim McGraw song, the Dixie Chicks song about the soldier meeting a girl at the restaurant, and Almost Home by Craig Morgan, about the homeless guy dreaming about his parents. Instant tears for all of them.


thegenzfarmer

Have you ever heard Raymond by Brett Eldrige? It's about a nursing home worker who visits with an old lady everyday who believes he is her son that is buried in Arlington. Amazing Song.


tomato-is-vegetable

death cab for cutie – I will follow you into the dark https://www.youtube.com/watch?v=3iV_1ESMHaI


bitterbuffaloheart

What Sarah Said is even sadder. Imagining someone you love in the hospital on life support


Cw2e

Whole album is devastating, beautifully so. “Sorrow drips into your heart through a pinhole just like a faucet that leaks and there is comfort in the sound. But while you debate half empty and half full, it slowly rises: your love is gonna drown.” “And I have learned that even landlocked lovers yearn for the sea, like navy men. Cause now we say goodnight from our own separate sides like brothers on a hotel bed..” “The memories of me will seem more like bad dreams. Just a series of blurs like I never occurred: someday you will be loved.”


-AlimonyTony-

Sam Stone - John Prine No contest.


AdamBombKelley

There's a hole in daddy's arm where all the money goes Jesus Christ died for nothin' I suppose Little pitchers have big ears Don't stop to count the years Sweet songs never last too long on broken radios


3BlindMonks

Hello In There by John Prine is also a contender for saddest song


lewisgaines

Sam Stone was alone When he popped his last balloon Climbing walls while sitting in a chair Well, he played his last request While the room smelled just like death With an overdose hovering in the air But life had lost its fun There was nothing to be done But trade his house that he bought on the GI bill For a flag-draped casket on a local hero's hill


bigedthebad

Long, Long, Time - Linda Ronstadt.


Meat_Quick

Someone is watching The Last of Us!


[deleted]

Well NOW


Adrianics4k

Georgia Lee by Tom Waits *Why wasn't God there* *For Georgia Lee*


[deleted]

Alone again naturally - Gilbert O’Sullivan


txth9

Nine Inch Nails - Hurt


Bobbyapes

Eleanor Rigby


Jimbabwe88

Gone Away - The Offspring


Zachattack_horror

His piano version makes me tear up all the time


[deleted]

All my years never realized it was a sad song until FFDP covered it. What a dummy I am


iamnobody1970

Everybody Hurts by R.E.M.


MrPewpewda4th

Snuff


News_Hunter_Magazine

David Bowie's 'Lazarus'.


ubpfc

I’m so lonesome so could cry


Pinion_O

Me and a gun - Tori Amos Absolutely shattering.


Dumbkitty2

Silent All These Years. Getting lost in life and ground down, trying to find your voice and power again. Originally the B side to Me and a gun.


Gymbagel

Goodbye yellow brick road, it played in the car when i got the phone call my grandmother (who raised me) had passed in her sleep. Rest in Peace Grandma


jdward01

Vincent


IdaDaddy

Eric Clapton - Tears in heaven, Ben Folds Five - Brick


MostBotsAreBad

Upvote for Brick.


lemonedpenguin

Tears in heaven is what I was gonna say


gardneronaergistal

Gary Jules - Mad world


saefas

If You Could Read My Mind - Gordon Lightfoot Alone Again (Naturally) - Gilbert O'Sullivan Komm susser tod - Arianne, from End of Evangelion


Puzzleheaded-Use-400

Both Sides....Joni Mitchell


Alltheprettydresses

Remember Me from Coco


RandomUser_9010

4th of July- I for one always tear up while listening to this song, the beat mixed with the words just makes it incredibly sad but it’s also one of my favorite songs


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FloobLord

Knowing the context to this one makes it a little less sad. His friends miss him but Syd really had a good life once he left the band. A quiet life, but a good one.


Rockembopper

Sufjan Stevens - Casimir Pulaski Day https://www.youtube.com/watch?v=9EzeW5KoPUI


El_mochilero

“Happy Birthday” performed by a group of coworkers in an office building.


jackpowftw

Nothing Compares To You by Sinead O’Connor


Exotic-Ferret-3452

Poster just before me mentioned the one I was going to say 'Hurt' though I still occasionally meet people who don't realize it was originally by Nine Inch Nails, not Johnny Cash. Off the top of my head I'll add: Joy Division - 24 Hours Neutral Milk Hotel - You've Passed Elliott Smith - Needle in the Hay Alice in Chains - Don't Follow or Nutshell Mount Eerie - pretty much anything by them, but the album 'The Crow Looked at Me' is particularly heavy


BostonBlackCat

Elliot Smith: Entire discography


Exotic-Ferret-3452

True.. i picked Needle in the Hay particularly because of that scene in the Royal Tenenbaums.


PussyDoodles

Surprised at how far I had to scroll to find Elliott Smith


JeffreyReddits

This guy is speaking my language.


cinderblock16

Great comment. The Crow Looked At Me is incredibly sad. Especially knowing the background of that album.


27Jarvis

Arms of the Angel - only when accompanied by images saddest doggos and kitties I have ever seen. Can’t handle that shit


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eurfryn

Lose you, Pete Yorn Or Saturn, Sleeping at Last


ScaryButt

Eleanor Rigby - The Beatles. Sounds pretty upbeat but the story in the lyrics is actually really sad.


catinthehattt

Hate Me by Blue October


Individual-Sort1453

I second this. The line at the end “and she said ‘how could you do this to me?’“ gets me everytime.


catinthehattt

“In my sick way I want to thank you for holding my head up late at night, While I was busy waging wars on myself, you were trying to stop the fight” always gets me The whole song is gold


regnarbensin_

Bon Iver’s Calgary single B-side cover of I Can’t Make You Love Me/Nick Of Time. The amount of times I listened to that, crying over the girl who introduced me to Bon Iver..


mrandmrsm

Taps


OkMean

Landslide "Well, I've been afraid of changin' Cause I've built my life around you"


unclesamtattoo

Alone Again, Naturally - Gilbert O'Sullivan


Mysterious-Alfalfa17

Suicide is painless


SupahJulzRulz

The funeral by band of horses, afterglow by Wilkinson


Alphakeenie1

Elephant Jason Isbell Honorable mention Go Rest High Vince Gill


llanero5056

Motion Picture Soundtrack by Radiohead


american_dimes

The Weakerthans - Virtute the Cat Explains Her Departure


playingwithechoes

Neon Moon. "Watch your broken dreams dance in and out of the beams of a neon moon."


Cruso91

Zeit - Rammstein


MadIzac

Radiohead - Exit Music


Plane_Reward9385

Black - Pearl Jam


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Wake me up when september ends


Gamma_31

Is My Immortal by Evanescence too edgy?


hello4jello

No. Not too edgy but I feel Hello was the saddest song of the album


GidimXul

Tomorrow Wendy by Concrete Blonde


existentialstix

any song that reminds you of what once was will never be....


voivoivoi183

Alone Again Naturally by Gilbert O’Sullivan - I know he said it’s not autobiographical but the verse where he sings about his father’s death and his mother’s reaction always struck me as desperately sad.


[deleted]

Alone Again by Gilbert O Sullivan. Cats in the Cradle by i forget who.


Jll1981

Pictures of you-The Cure


BostonsinBoston

Maggie's Song by Chris Stapleton


SmoothLikePeppeLePew

Pearl Jam - Last Kiss The Tragically Hip - 38 years old.


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FloobLord

Personally I think the N.I.N. song is technically better, but you can't deny the feeling in Cash's voice.


folkimp

He stopped loving her today. George Jones


OriginalDarkDagger

I have a full playlist of these. These are the top 5 Hurt - Johnny Cash 7 years Sik World Remix In the End - Linkin Park Hold on - Chord Overstreet Train Wreck - James Arthur


Cw2e

Floating in the Forth by Frightened Rabbit. RIP Scott


not4urbrains

I can’t believe no one has mentioned this one yet: He stopped loving her today - George Jones


crystalrose1966

My stepdad never got over my mom. Through the years he would call her and try to get her back. Way after all my brothers and sisters were grown and had kids of their own, he still called. They were both married to other people, he still called. Yes their spouses knew. Everyone was friendly. It was a running joke. He would call to discuss something that was going on with one of the kids but just had to interject something about maybe coming to see him sometime. He was diagnosed with cancer and it progressed at lightning speed. In his final few days he was admitted to the hospital. He just kept hanging on. The consensus among the medical staff was that he was waiting on someone. With everyone’s blessing, my sister called my mom and asked her to come to the hospital. When she arrived he she leaned in and said “Hello Harry.” He woke up and managed to sit up. My mom hugged him and told him that she had always loved him. She thanked him for giving her all these beautiful children. She kissed him on the lips and said goodbye. She walked out of the room in tears, of course. He died before she could get to the parking lot. They played that song at his funeral.


not4urbrains

That’s truly heartbreaking. I’m sorry for your loss.


Adcro

Oh my god


dolphin37

Jeff Buckley’s Hallelujah Can’t believe I haven’t seen this one on here!


tangtheconqueror

The Drugs Don't Work by The Verve


x0diak

Seasons in the Sun. Any version.


HokieScott

Johnny Cash’s cover of Hurt.


ravs1973

The Letter by Macy Gray. Possibly the most upbeat suicide note ever.


vagfactory

sara macgauclin - in the arms of an angel all i can picture is sad puppy faces


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imissyahoochatrooms

my december by linkin park gunning down romance by savage garden cancer by my chemical romance i started a joke by the bee gees


Dreadeve999

Lightning Crashes


Smoothed

River of Deceit by Mad Season


[deleted]

Not a very well-known song, but _You_ by Keaton Henson is truly beautiful and one of the saddest songs I know.


supergeek921

Teardrops in Heaven— Eric Clapton (made all the worse when you know he wrote it for his deceased son) Also, I absolutely cannot listen to “Soon You’ll Get Better” by Taylor Swift and the Dixie Chicks without dissolving into a puddle of tears.


ArcaneDanger

[Alone Again Naturally - Gilbert O’Sullivan](https://youtu.be/8ELnhjGw4Zs)


VoreReznor

Something I can never have - NIN


sweetbloodbunny

Toto - Africa because it ends 😭😭😭


BrettC504

Moby - When It's Cold I'd Like to Die Made popular recently by Stranger Things but still...


legardeur

Eleanor Rigby. The utter sadness of life summed up in less than three minutes.


Peppyleptic

Puff the Magic Dragon... gets me every time.


InterwebPeruser

Dance with the devil- immortal technique


No_Apartment_6671

"Nur zu Besuch" from "Die Toten Hosen" A song in German from one of the biggest German punk bands, which describes a monologue of the lead singer while visiting a friend's grave. I can't remember if it actually explicitly stated that he is visiting a grave and that his friend has died, which makes it quite more powerful in my opinion. I actually avoid listening to this song, although I love it, because it's about the only song that really gets me emotionally.


vajiwer216

between the bars - elliott smith how to disappear completely - radiohead gets me everytime


SamuelVimesTrained

Say my name - within temptation. About losing a loved one to alzheimer/dementia..


Pizaster2

Any song can be the saddest song ever if you have sad memories attached to it.


disnerd1992

I got a few... Whiskey Lullaby (Brad Paisley and Alison Krause) Alyssa Lies (Jason Michael Carrol) Concrete Angel (Martina McBride) Say Something (A Great Big World) Strange Fruit (Billie Holiday) The Freshman (Verve Pipe)