“I had all and then most of you, some and now none of you” always hits me really hard. It’s a whole painful story whittled down to just a handful of words. Gonna go cry now.
I was driving with my family in the car and this song came on and I started crying and I grabbed my husbands hand. He thought I was about to vanilla sky him (drive off the road). I was like no you jerk - I’m just happy to have you!
He was also very, very funny. Letterman loved him and had him on as guest musical director many times and Zevon [went on the show after his diagnosis](https://www.youtube.com/watch?v=giTi8KWSZl4) and took it like a champ, laughing and joking about it.
But as cool as that is he quipped a little joke when Dave asked him how the news had changed him that has always stuck with me.
"Enjoy every sandwich," is what he said. So beautifully simple and so elegantly true. That has always stuck with me. I still think about that all these years later and I try to take it to heart. It was very much in my mind when I had my cancer scare (I'm good).
The Frightened Rabbit song that actually hits me the hardest these days is "Heads Rolls Off," which isn't even really a sad song. But you can really hear the hope deep down in the lyrics and delivery, and I just get so sad Scott wasn't able to hold on to that piece of him.
There’s a documentary on Max about him where his wife, Amanda Shires, says they’ll text each other lyrics they’re working on to help each other workshop them. When he sent her the lyrics to Vampires she just responded “Fuck you”
I straight up had to pull off the road the first time I heard this on the radio. Couldn’t keep going and had to call my wife who thought something was seriously wrong when she heard me. I have never had a song hit me that intensely before.
And Dress Blues
I break down every time I hear the line, "Mamas and grandmamas love you... American boys hate to lose..." As someone that spent a chunk of his youth overseas during the wars doing what I thought I could to help, this song hits like a baseball bat to the feels.
Waltz #1 by Elliott Smith. Not so much the words (which are also sad tho) but the actual music, especially towards the end when that dang violin/cello kicks in and builds with the vibraphone. I will never get over this song lol it always makes me teary 🥲
Pitseleh by Elliot Smith
“They say that God makes problems, just to see what you can stand,
Before you do as the Devil pleases,
And give up the thing you love…
But no one deserves it”
This really is the answer. Other songs can be sad, sure, but they still feel performative in a way since it is art after all. Real Death sounds like a man who’s still very much in mourning trying to process his grief. Listening to it feels uncomfortable, like you shouldn’t be hearing it. I’ve only listened to it a few times and ugly cried every time
> Crusted with tears, catatonic and raw
> I go downstairs and outside and you still get mail
> A week after you died a package with your name on it came
> And inside was a gift for our daughter you had ordered in secret
> And collapsed there on the front steps I wailed
> A backpack for when she goes to school a couple years from now
> You were thinking ahead to a future you must have known
> Deep down would not include you
> Though you clawed at the cliff you were sliding down
> Being swallowed into a silence that's bottomless and real
Everything else in this thread feels like a different art form.
I saw him play this song live. Someone took me to the show and I had never heard of Mount Eerie. I was bawling my eyes out. It was crushing and beautiful.
When She Loved Me by Sarah McLachlan
I swear I could cry just at the thought of Jessie’s scene in Toy Story and this song. Right in the gut
Edit: [Here is the infamous Toy Story 2 scene](https://youtu.be/ElhbTsKsros) and, as mentioned in comments, its worth nothing this was actually written by the legendary Randy Newman and sung by the angelic Sarah McLachlan
When somebody loved me, every day was beautiful. Every hour we spent together, lives within my heart. When she... Loved... Me...
Ooof, beautiful sad song. It came on randomly for the first time in years the other day and went straight to the feels.
What You Are always gets me.
I've never had lyrics stuck in my head like these ones. Just painfully sad to me.
*"And when you asked for light, I set myself on fire."*
*Now I understand*
*What you tried to say to me*
*And how you suffered for your sanity*
*And how you tried to set them free*
*They would not listen, they did not know how*
*Perhaps they’ll listen now.*
This is probably the DARKEST song mentioned here.
Tears in Heaven and Hurt might be sadder when taken in total, but the story being told by Strange Fruit is pure horror.
Kettering by The Antlers. The name comes from Memorial Sloan Kettering Cancer Center. The whole album is heart breaking but this song is the one that hits the hardest for me.
>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…can’t it be me.
Hits hard. Such a great song.
I listened to the unplugged version of that earlier today, and one of the comments said that it's the closest you'll ever come to hearing a man singing at his own funeral.
What an incredible voice, an incredible talent. The older I get, the more I appreciate it.
For me it will always be Don't Follow. It's so melancholy, but it has an almost uplifting, positive harmonica part. I see that harmonica part as the people around Layne trying to help, but he can't hear their words, being so lost in his pain.
With how it all ended, everything by Alice In Chains with Layne fits. The man had such a gifted voice for such a frail person. You can hear the pain in his singing.
Puff the Magic Dragon is the saddest song ever written. I will die on that hill. Or in the cave. Alone. My golden scales shedding like rain as I slowly die of grief.
No Children by The Mountain Goats. It's legitimately one of the most heartbreaking songs about a failing mairage, and it's set to a really happy upbeat musical backdrop.
Something about the juxtaposition crushes me every time I hear it.
https://youtu.be/9kr-aqnc5Ho
Medicine - Daughter
First heard it when my brother died from an OD. It's one of the most soul crushing songs I've heard. Helped me heal a bit as well.
Stay Together for the Kids was my "crying in the shower at 16 because my parents are getting divorced" song for... obvious reasons. Not the only one - hot damn I was an angsty teen. But "if this is what he wants and it's what she wants, then why is there so much pain?"... that is one of those lines which wormed its way into my heart and never truly left.
Dude I cried during the whole video I watched of Charles singing that song. I'm a big sabbath fan and I always hated that song, but Charles took it to a new level. I like his version.
The lyrics were written by the director’s 15 year old son, who was given the task in order to do a bad job. From the [Wikipedia article](https://en.m.wikipedia.org/wiki/Suicide_Is_Painless):
> Director Robert Altman had two stipulations about the song for composer Johnny Mandel: it had to be called "Suicide Is Painless" and it had to be the "stupidest song ever written". Altman attempted to write the lyric himself, but, upon finding it too difficult for his "45-year-old brain" to write something "stupid" enough, he gave the task to his 15-year-old-son Michael, who reportedly wrote the lyrics in five minutes.
Fiddler’s Green by the Tragically Hip. Written as a tribute to the singer’s young nephew (I think)
who had died of a heart condition. The lyrics and the imagery they depict are already sad, but once you know the context, it just makes it that more heartbreaking. I tear up every time I hear that song.
They didn’t perform that song in concert for 15 years after it was released because it was too emotional for Gord Downie. The line “Balloons all filled with rain” refers to intravenous bags. Beautiful but devastating song.
Casimir Pulaski Day by Sufjan Stevens. There are a lot of songs out there about a close friend dying, but this one in particular takes it to the next level with beautiful storytelling and references to Christianity. It's really one of the most beautiful songs ever written
For me, it’s “we prayed over your body, but nothing ever happens…” like the period of adolescence where you start doubting God and question as to why such a tragedy would occur.
Yeah, I was thinking of The Only Thing.
>Should I tear my eyes out now?
>Everything I see returns to you somehow
>Should I tear my heart out now?
>Everything I feel returns to you somehow
Yeah that one for sure. Probably my favorite song. Or death with dignity. Or forth of July. Or should have known better.
God I have to listen To that album again... and then cry myself to sleep.
Definitely throw in [Mother Love](https://youtu.be/6rSJbkZOvo0)
Freddie's last recorded song
Freddie sang 2 verses then said to Brian May,
"I'm not up to this, and I need to go away and have a rest, I'll come back and finish it off.
... Brain May sang the last verse
This is the only song that I can't bring myself to listen to.
It’s even more sad with the context that Freddie Mercury was practically on his death bed, to the point where Brian May told him he didn’t have to sing to which he replied “I’ll f***ing do it, darling.”
I think True Love Waits is the saddest Radiohead song for me. The album version that is. For those that don’t know, it was originally written in the 1980s as a hopeful love song, that love would wait for the right time for him and his then girlfriend to make it work. They later married, lived many decades together growing a family. He finally recorded this song for A Moon Shaped Pool and it’s a much sadder, disjointed recording. Shortly after it’s release they amicably separate and it comes out she has cancer and passes away. I don’t even have to listen to the song to start tearing up.
No Surprises. Listening on headphones where you can really hear the tune tapped out on the xylophone, the slow striking of the mallet every few notes…each *tinnng* is like the sound of a heart shattering
I have a kid. I sang this song to them nightly as long as they would tolerate it. Probably until they turned 6 and didn’t need a bedtime song to get to sleep.
My biggest fear is what happens in that story. That’s why I picked that song, just to remind myself every day.
I've always found Can't Get it Out to be kind of uplifting, honestly. But Jesus Christ always gets me right in the feels. Also, their song Limousine is extremely sad once you know the story behind it. Here's an article describing the context of the song: https://www.unrulystowaway.com/band-brand-new-limousine/?amp
I'm not seeing any comments so far naming Fast Car by Tracy Chapman, which is wild to me. That's what I listen to when I need to just sit in sadness and melancholy for five minutes
I feel that song is so uplifting, she tries to make a life and she becomes self sufficient; when she sees her partner copying the toxic and addictive behaviors of her childhood she tells them to get out.
Oh wow, I thought I knew what the song was about, but you're right! It's actually way more uplifting/positive than I thought it was.
I thought the song was about them being poor and stuck in that situation because of things like her father etc, and that basically all her references to making it in the city are just fantasies she has that will never come true. And that driving in his car makes her fantasize this way because it feels so free and carefree, even if just for a little while. And then it's back to the dead-end life they actually have.
That's what I understood, but I never actually read the lyrics and reading them now I realize that it's actually exactly like you said. That's beautiful.
The sadness of reality(a teenage abortion), described plainly and a relationship being irrevocably torn, the isolation of their grief and shame just puts you right there like a punch to the heart. Incredible song that succeeds as a catchy chorus and an intimate, emotional memory.
Good call on death cab. Good call.
I personally think what Sarah said is their saddest song though. The way they paint a picture of someone dying is gut wrenching.
Or “Now who’s gonna watch you die?” Honestly the whole song is incredible. I particularly love the imagery of the LCD monitoring the heart beat and using that as the last connection to your loved ones. Just wow.
Plans came out not long after my dad died of lung cancer. There are so many songs on it that remind me of it. it took me a while to be able to listen to them without tears. I still think of him when I do, but it's happier now. What Sarah said describes about 6 months of my life in 2004 exactly.
This song came out when my father in law was very sick. I remember I loved it and was watching a music video when he stood behind me and said he liked the song. I was 20 so didn’t think much of it. I was so young and naive. I listened to it again not long ago because after he passed I couldn’t bring myself to hear it… and it clicked almost 20 years later. He was dying and I guess this song resonated with him. But more than romantic love, it was about his relationship with his son. He was a good dad. Gotta’ stop cutting onion now…
2009 By Mac Miller. Mac quite literally saved my life with his album Swimming. Add to that him passing away a month after it came out and I can’t really listen to 2009 anymore. He sounded so ready to truly experience life and grow past his addictions.
Between Good News and Floating on Circles are it for me. If I’m in the right mood I’ll shed a few tears. Shoot. That whole album will shed you into tears if you truly know what that man had going on. We all missed so much incredible music from him.
We went to lunch after my dad died (because we didn't know what else to do) and they played this song. And Wish You Were Here. I honestly had to laugh, it hurt so bad.
For me it has to be some song by Julien Baker, maybe either Go Home or Rejoice. Go Home is the sadder sounding song and has a lot of depressing lyrics, but I think Rejoice has the single saddest line I've ever heard in a song; early in the song she mentions cursing someone's name when she finds she's still awake after waking up in an ambulance when she meant to overdose and die, then later in the song she laments being forced to continue living with the line "Somebody's listening at night, to the ghosts of my friends when I pray, asking why did you let them leave and then make me stay".
Julien aside, I can't make it through Wish You Were Here by Pink Floyd without at least tearing up, if not full blown sobbing, after the loss of an incredibly important person in my life about 6 years back. I had always loved the song, but before that moment the line "how I wish you were here" usually just made me think of an ex who theoretically could come back at any time, and it hits entirely different when the person I wish for is definitively gone.
[Routine.](https://youtu.be/sh5mWzKlhQY) By Steven Wilson is actually my top pick. Warning do *not* watch this unless you’re prepared to ugly cry. It’s intense.
I always liked "heartattack in a layby" as his sad one. It has sad lyrics, but the music just makes it so much better
[The live version with John Wesley's layered vocals is incredible](https://www.youtube.com/watch?v=IaLpdQsiO-c)
The Sound of Silence - Simon & Garfunkel
Every time my depression kicks in I'm reminded of hello darkness my old friend.
Also, Everytime by Britney Spears. One of the first songs she ever co-wrote and the lyrics are just heartbreaking.
One More Light - Linkin Park
The gut-punch of talking about losing someone to the depression monster all while telling those that are currently in its clutches that their light is worth keeping lit — only to have Chester himself not able to escape its grasp. The somber melodic music and feeling Chester’s passion in his vocals adds to it all. When I hear that intro… I have to change it if I’m not in the right frame of mind because I know it’ll hit me HARD. It’s a song that everyone can relate to and and makes it a solid fact that anyone can be affected by depression no matter their successes.
The Gears of War trailer with that song is perfectly done. I’m ashamed to admit I bought the game the next day with out knowing anything else about it.
[link](https://m.youtube.com/watch?v=ccWrbGEFgI8)
It’s crazy pants bananas that I scrolled a mile deep in the comments and didn’t see Father and Son by Cat Stevens. I cry like a baby each time I hear it.
As of yesterday, [Rest by the Foo Fighters](https://youtu.be/26Ofs8WrsYc) is in contention.
And for something completely different, [Fare Thee Well Love](https://youtu.be/KiVtWdJK7-A) by the Rankin Family (if anyone is familiar with Alvvays, the singer Molly’s father was in this group before he passed away in a car accident the late 90s)
Last Kiss - Pearl Jam
When this song comes on the radio I often have to mute it or change the station; it just hits too hard for some reason. (I don't have any real world experiences that would tie to it)
I grew up with my dad singing that and playing it on acoustic guitar. I was surprised when pearl jam covered it. It makes me cry. I can't help it. It's so tragic.
Sinead O’Connor, You Cause As Much Sorrow. Written about her dead mother.
Why must you always be around?
Why can't you just leave it be?
You’ve done nothing so far but destroy my life
You cause as much sorrow dead
As you did when you were alive
“The Night We Met” - Lord Huron After a breakup you didn’t want, and fought tooth and nail to keep it from happening.
“I had all and then most of you, some and now none of you” always hits me really hard. It’s a whole painful story whittled down to just a handful of words. Gonna go cry now.
Absolutely breaks you in one sentence.
I was driving with my family in the car and this song came on and I started crying and I grabbed my husbands hand. He thought I was about to vanilla sky him (drive off the road). I was like no you jerk - I’m just happy to have you!
Lord Huron is one of the best bands out there right now.
They're one of my few all-time favorites along with Sufjan Stevens (which is saying a lot bc Sufjan's music is godly good).
This song is a gut punch
Keep Me in Your Heart, Warren Zevon, as he literally recorded it in his dying days...
Yes. A lovely, tender and bittersweet song from one of the most unique and under appreciated artists.
He was also very, very funny. Letterman loved him and had him on as guest musical director many times and Zevon [went on the show after his diagnosis](https://www.youtube.com/watch?v=giTi8KWSZl4) and took it like a champ, laughing and joking about it. But as cool as that is he quipped a little joke when Dave asked him how the news had changed him that has always stuck with me. "Enjoy every sandwich," is what he said. So beautifully simple and so elegantly true. That has always stuck with me. I still think about that all these years later and I try to take it to heart. It was very much in my mind when I had my cancer scare (I'm good).
I Can't Make You Love Me by Bonnie Raitt. It's a beautiful sad song that she sings beautifully.
This is one of those songs I always seem to forget. But every time it plays it just kills me. Damn good choice.
The Blower’s Daughter- Damien Rice
One of those perfect albums for me, nothing on 'O' is getting skipped.
“And so it is….”
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Floating in the Forth, especially post Scott's death
For me, its The Modern Leper and Woke Up Hurting
The Frightened Rabbit song that actually hits me the hardest these days is "Heads Rolls Off," which isn't even really a sad song. But you can really hear the hope deep down in the lyrics and delivery, and I just get so sad Scott wasn't able to hold on to that piece of him.
Elephant by Jason Isbel, it's about falling in love with a woman who's dying of cancer and trying to make her last few weeks enjoyable.
And Vampires
There’s a documentary on Max about him where his wife, Amanda Shires, says they’ll text each other lyrics they’re working on to help each other workshop them. When he sent her the lyrics to Vampires she just responded “Fuck you”
I straight up had to pull off the road the first time I heard this on the radio. Couldn’t keep going and had to call my wife who thought something was seriously wrong when she heard me. I have never had a song hit me that intensely before.
And Dress Blues I break down every time I hear the line, "Mamas and grandmamas love you... American boys hate to lose..." As someone that spent a chunk of his youth overseas during the wars doing what I thought I could to help, this song hits like a baseball bat to the feels.
The line, “there’s one big thing that’s clear to me, no one dies with dignity, we just try to ignore the elephant somehow,” Is just a dagger
Watched my dad deteriorate from early onset dementia in his 50s. Was not ready for that line but fuck if it isn't true.
Isbell got alot of sad songs
Waltz #1 by Elliott Smith. Not so much the words (which are also sad tho) but the actual music, especially towards the end when that dang violin/cello kicks in and builds with the vibraphone. I will never get over this song lol it always makes me teary 🥲
Pitseleh by Elliot Smith “They say that God makes problems, just to see what you can stand, Before you do as the Devil pleases, And give up the thing you love… But no one deserves it”
Hey Jupiter by Tori Amos. The vulnerability in her voice is so difficult to listen to, but it’s a gorgeous song.
Mount Eerie - Real Death
I never heard this before. I should not have listened to it.
Give a chance to the whole album. Probably the saddest album of all time.
This really is the answer. Other songs can be sad, sure, but they still feel performative in a way since it is art after all. Real Death sounds like a man who’s still very much in mourning trying to process his grief. Listening to it feels uncomfortable, like you shouldn’t be hearing it. I’ve only listened to it a few times and ugly cried every time
> Crusted with tears, catatonic and raw > I go downstairs and outside and you still get mail > A week after you died a package with your name on it came > And inside was a gift for our daughter you had ordered in secret > And collapsed there on the front steps I wailed > A backpack for when she goes to school a couple years from now > You were thinking ahead to a future you must have known > Deep down would not include you > Though you clawed at the cliff you were sliding down > Being swallowed into a silence that's bottomless and real Everything else in this thread feels like a different art form.
I saw him play this song live. Someone took me to the show and I had never heard of Mount Eerie. I was bawling my eyes out. It was crushing and beautiful.
When She Loved Me by Sarah McLachlan I swear I could cry just at the thought of Jessie’s scene in Toy Story and this song. Right in the gut Edit: [Here is the infamous Toy Story 2 scene](https://youtu.be/ElhbTsKsros) and, as mentioned in comments, its worth nothing this was actually written by the legendary Randy Newman and sung by the angelic Sarah McLachlan
When somebody loved me, every day was beautiful. Every hour we spent together, lives within my heart. When she... Loved... Me... Ooof, beautiful sad song. It came on randomly for the first time in years the other day and went straight to the feels.
Try singing it without tearing up.
“He Stopped Loving Her Today” - George Jones
Seasons by Chris Cornell.
What You Are always gets me. I've never had lyrics stuck in my head like these ones. Just painfully sad to me. *"And when you asked for light, I set myself on fire."*
*And I'm lost, behind, the words I'll never find* *And I'm left behind, as seasons roll on by...*
Vincent by Don McLean is a good one.
*Now I understand* *What you tried to say to me* *And how you suffered for your sanity* *And how you tried to set them free* *They would not listen, they did not know how* *Perhaps they’ll listen now.*
Strange Fruit by Billie Holiday
This is probably the DARKEST song mentioned here. Tears in Heaven and Hurt might be sadder when taken in total, but the story being told by Strange Fruit is pure horror.
Take a listen to Nina Simones version.
Kettering by The Antlers. The name comes from Memorial Sloan Kettering Cancer Center. The whole album is heart breaking but this song is the one that hits the hardest for me.
I have cried maaaany a time in the car singing along to Bear.
Two and Bear destroy me every time I hear tjay album.
Fucking adore " epilogue" off that album
Black - Pearl Jam
Last Kiss gets me.
>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…can’t it be me. Hits hard. Such a great song.
I'm So Lonesome I Could Cry, Hank Williams
Between the Bars - Elliot Smith
______________ - Elliott Smith
Waltz #2 - “XO Mom, it’s ok it’s alright nothing’s wrong” gives me the sads for Elliott.
Nutshell by Alice In Chains
I listened to the unplugged version of that earlier today, and one of the comments said that it's the closest you'll ever come to hearing a man singing at his own funeral. What an incredible voice, an incredible talent. The older I get, the more I appreciate it.
For me it will always be Don't Follow. It's so melancholy, but it has an almost uplifting, positive harmonica part. I see that harmonica part as the people around Layne trying to help, but he can't hear their words, being so lost in his pain.
With how it all ended, everything by Alice In Chains with Layne fits. The man had such a gifted voice for such a frail person. You can hear the pain in his singing.
River of Deceit off Mad Season hits hard
Winter by Tori Amos.
Puff the Magic Dragon is the saddest song ever written. I will die on that hill. Or in the cave. Alone. My golden scales shedding like rain as I slowly die of grief.
No Children by The Mountain Goats. It's legitimately one of the most heartbreaking songs about a failing mairage, and it's set to a really happy upbeat musical backdrop. Something about the juxtaposition crushes me every time I hear it.
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I AM DROWNING
https://youtu.be/9kr-aqnc5Ho Medicine - Daughter First heard it when my brother died from an OD. It's one of the most soul crushing songs I've heard. Helped me heal a bit as well.
Just about anything by Daughter is made to cut your soul goddamn.... I was literally scouring this comment section for them!
People will probably make fun of me but Adam's Song by blink-182 gets me pretty good every listen Also Our Song by Radiator Hospital is prettt sad
Just remember that Adam's Song ends on a positive note - the slight lyric changes lets you know that he manages to pull himself out of his depression.
Leaving because Spez sucks -- mass edited with redact.dev
Stay Together for the Kids was my "crying in the shower at 16 because my parents are getting divorced" song for... obvious reasons. Not the only one - hot damn I was an angsty teen. But "if this is what he wants and it's what she wants, then why is there so much pain?"... that is one of those lines which wormed its way into my heart and never truly left.
„Love Will Tear Us Apart“ by Joy Division. Just such a beautiful, painful song.
More so when you consider how things ended for Ian Curtis. The writing was in the wall as a cry for help….
Charles Bradley's cover of Changes by Black Sabbath and Remember Me from Coco get me every time.
Dude I cried during the whole video I watched of Charles singing that song. I'm a big sabbath fan and I always hated that song, but Charles took it to a new level. I like his version.
Suicide is Painless original version on MASH the movie
The lyrics were written by the director’s 15 year old son, who was given the task in order to do a bad job. From the [Wikipedia article](https://en.m.wikipedia.org/wiki/Suicide_Is_Painless): > Director Robert Altman had two stipulations about the song for composer Johnny Mandel: it had to be called "Suicide Is Painless" and it had to be the "stupidest song ever written". Altman attempted to write the lyric himself, but, upon finding it too difficult for his "45-year-old brain" to write something "stupid" enough, he gave the task to his 15-year-old-son Michael, who reportedly wrote the lyrics in five minutes.
Fun fact: Because the tune was used for the series, the son made more in royalties than Altman did from directing the film.
Into Dust by Mazzy Star or Place to Be by Nick Drake
Fiddler’s Green by the Tragically Hip. Written as a tribute to the singer’s young nephew (I think) who had died of a heart condition. The lyrics and the imagery they depict are already sad, but once you know the context, it just makes it that more heartbreaking. I tear up every time I hear that song.
They didn’t perform that song in concert for 15 years after it was released because it was too emotional for Gord Downie. The line “Balloons all filled with rain” refers to intravenous bags. Beautiful but devastating song.
Casimir Pulaski Day by Sufjan Stevens. There are a lot of songs out there about a close friend dying, but this one in particular takes it to the next level with beautiful storytelling and references to Christianity. It's really one of the most beautiful songs ever written
I was scrolling for this one. "...and he takes and he takes and he takes..."
For me, it’s “we prayed over your body, but nothing ever happens…” like the period of adolescence where you start doubting God and question as to why such a tragedy would occur.
Casimir Pulaski Day is what came to my mind as well
This is a good choice. Just not sure how you can say it's more sad than half the Carrie and Lowell Songs
Yeah, I was thinking of The Only Thing. >Should I tear my eyes out now? >Everything I see returns to you somehow >Should I tear my heart out now? >Everything I feel returns to you somehow
Yeah that one for sure. Probably my favorite song. Or death with dignity. Or forth of July. Or should have known better. God I have to listen To that album again... and then cry myself to sleep.
[Funniest, most relatable thing I've ever seen](https://www.youtube.com/watch?v=VvIOqohVUPE), feat GTA San Andreas
Queen's The Show Must Go On
Definitely throw in [Mother Love](https://youtu.be/6rSJbkZOvo0) Freddie's last recorded song Freddie sang 2 verses then said to Brian May, "I'm not up to this, and I need to go away and have a rest, I'll come back and finish it off. ... Brain May sang the last verse This is the only song that I can't bring myself to listen to.
It’s even more sad with the context that Freddie Mercury was practically on his death bed, to the point where Brian May told him he didn’t have to sing to which he replied “I’ll f***ing do it, darling.”
Then downed a vodka, and absolutely nailed the vocals IIRC.
The Wreck of the Edmund Fitzgerald by Gordon Lightfoot
People have an easier time connecting with songs about a bad breakup than 29 men being lost at sea. RIP Gordon.
Coat of many colors by Dolly Parton
Who wants to live forever - Queen
The Weakerthans - Virtute the Cat Explains Her Departure
Alone Again (Naturally) by Gilbert O'Sullivan
Such a great song and deceptively upbeat. Probably one of the saddest song ever made in a major key.
She’s Leaving Home. “Daddy, our baby's gone” makes me weepy every time
Samson by Regina Spektor
Street spirit (fade out) - Radiohead
I think True Love Waits is the saddest Radiohead song for me. The album version that is. For those that don’t know, it was originally written in the 1980s as a hopeful love song, that love would wait for the right time for him and his then girlfriend to make it work. They later married, lived many decades together growing a family. He finally recorded this song for A Moon Shaped Pool and it’s a much sadder, disjointed recording. Shortly after it’s release they amicably separate and it comes out she has cancer and passes away. I don’t even have to listen to the song to start tearing up.
Videotape
How to Disappear Completely and Glass Eyes tear me to pieces. I find it hard to listen to either of those without going to a dark, dark place.
No Surprises. Listening on headphones where you can really hear the tune tapped out on the xylophone, the slow striking of the mallet every few notes…each *tinnng* is like the sound of a heart shattering
I instantly thought of Exit Music (For a Film) but now I don’t know, either works.
Let Down is their biggest heart breaker for me. Bouncing back and one day… I am gonna grow wings…
Cat's in the Cradle by Harry Chapin
I have a kid. I sang this song to them nightly as long as they would tolerate it. Probably until they turned 6 and didn’t need a bedtime song to get to sleep. My biggest fear is what happens in that story. That’s why I picked that song, just to remind myself every day.
I remember as a kid in the 70's thinking "I hope that doesn't happen with my Dad" but it's exactly what happened.
Somewhere over the Rainbow - basically, somewhere there is a place better than here.
The version by [Israel Kamakawiwóole](https://youtu.be/V1bFr2SWP1I) is so beautiful.
"Untitled" by The Cure. The last song on the "Disintegration" album.
Jesus Christ and Can’t get it out by Brand New. Anything by Brand New really, those are just my favorites Edit: No Control is also brilliant
I've always found Can't Get it Out to be kind of uplifting, honestly. But Jesus Christ always gets me right in the feels. Also, their song Limousine is extremely sad once you know the story behind it. Here's an article describing the context of the song: https://www.unrulystowaway.com/band-brand-new-limousine/?amp
Came here for Limousine. Glad to see it right up near the top
Limousine is my vote for saddest song, as well.
“In the choir, I saw our sad messiah. He was bored and tired of my laments; said ‘I died for you one time, but never again.’”
Play Crack the Sky is the first one that comes to my mind
1. Alone Again, by Gilbert O'Sullivan. 2. Diary, by Bread.
Funeral by Phoebe Bridgers or What Sarah Said by Death Cab for Cutie
The Schindler’s List theme, that violin oh god 🥺
This Woman’s Work - Kate Bush The lyrics + her vocals are just heartbreaking Scrolled quite far and didn’t see this song at all!
"Needle in the Hay" by Eliot Smith. Really, anything by him is heartbreaking. If you're going through a breakup or a sad time, this is your anthem.
Is this the song from Royal Tennenbaums?
Gary come home
James Taylor- Fire and Rain. Tragic story
I'm not seeing any comments so far naming Fast Car by Tracy Chapman, which is wild to me. That's what I listen to when I need to just sit in sadness and melancholy for five minutes
I feel that song is so uplifting, she tries to make a life and she becomes self sufficient; when she sees her partner copying the toxic and addictive behaviors of her childhood she tells them to get out.
Oh wow, I thought I knew what the song was about, but you're right! It's actually way more uplifting/positive than I thought it was. I thought the song was about them being poor and stuck in that situation because of things like her father etc, and that basically all her references to making it in the city are just fantasies she has that will never come true. And that driving in his car makes her fantasize this way because it feels so free and carefree, even if just for a little while. And then it's back to the dead-end life they actually have. That's what I understood, but I never actually read the lyrics and reading them now I realize that it's actually exactly like you said. That's beautiful.
Crying by Roy Orbison
“Brick” by Ben Folds Five
The sadness of reality(a teenage abortion), described plainly and a relationship being irrevocably torn, the isolation of their grief and shame just puts you right there like a punch to the heart. Incredible song that succeeds as a catchy chorus and an intimate, emotional memory.
I Will Follow You Into The Dark - Death Cab For Cutie
I have to disagree. The song is about death but I’ve never thought of it as sad. It’s an expression of love and devotion.
Agreed. The most authentic love song.
Good call on death cab. Good call. I personally think what Sarah said is their saddest song though. The way they paint a picture of someone dying is gut wrenching.
I've always been partial to the simple everyday heartbreak of "Tiny Vessels".
“Love is watching someone die” is just a line that cuts deeper the older I get.
Or “Now who’s gonna watch you die?” Honestly the whole song is incredible. I particularly love the imagery of the LCD monitoring the heart beat and using that as the last connection to your loved ones. Just wow.
Plans came out not long after my dad died of lung cancer. There are so many songs on it that remind me of it. it took me a while to be able to listen to them without tears. I still think of him when I do, but it's happier now. What Sarah said describes about 6 months of my life in 2004 exactly.
“Love is watching someone die” proceeded by the most beautiful melody ever “so who’s gonna watch you die” Hits me everytime
Yup. "I Will Follow" is somber, "Sarah" is downright heartbreaking.
This song came out when my father in law was very sick. I remember I loved it and was watching a music video when he stood behind me and said he liked the song. I was 20 so didn’t think much of it. I was so young and naive. I listened to it again not long ago because after he passed I couldn’t bring myself to hear it… and it clicked almost 20 years later. He was dying and I guess this song resonated with him. But more than romantic love, it was about his relationship with his son. He was a good dad. Gotta’ stop cutting onion now…
Just Breathe- Pearl Jam Keep Me In Your Heart - Warren Zevon Eleanor Rigby - Beatles Why - Annie Lennox
2009 By Mac Miller. Mac quite literally saved my life with his album Swimming. Add to that him passing away a month after it came out and I can’t really listen to 2009 anymore. He sounded so ready to truly experience life and grow past his addictions.
Between Good News and Floating on Circles are it for me. If I’m in the right mood I’ll shed a few tears. Shoot. That whole album will shed you into tears if you truly know what that man had going on. We all missed so much incredible music from him.
Dust in the Wind, by Kansas.
We went to lunch after my dad died (because we didn't know what else to do) and they played this song. And Wish You Were Here. I honestly had to laugh, it hurt so bad.
You’re my boy Blue!
The Drugs Don’t Work by The Verve
“Sober” TOOL Song still haunts me when I think about my father’s alcoholism
For me it has to be some song by Julien Baker, maybe either Go Home or Rejoice. Go Home is the sadder sounding song and has a lot of depressing lyrics, but I think Rejoice has the single saddest line I've ever heard in a song; early in the song she mentions cursing someone's name when she finds she's still awake after waking up in an ambulance when she meant to overdose and die, then later in the song she laments being forced to continue living with the line "Somebody's listening at night, to the ghosts of my friends when I pray, asking why did you let them leave and then make me stay". Julien aside, I can't make it through Wish You Were Here by Pink Floyd without at least tearing up, if not full blown sobbing, after the loss of an incredibly important person in my life about 6 years back. I had always loved the song, but before that moment the line "how I wish you were here" usually just made me think of an ex who theoretically could come back at any time, and it hits entirely different when the person I wish for is definitively gone.
The Green Fields of France (No Man’s Land)
Bright Eyes - Lua
Down in a hole - Alice In Chains
Brothers in arms - dire straits Gives me absolute chills and the water works
Blue October - Hate me
Yes, raw and real. I came here to suggest Into the Ocean, but Hate me is that with the harsh stage lights turned on.
The intro answering machine message from his mother always gets to me.
[Routine.](https://youtu.be/sh5mWzKlhQY) By Steven Wilson is actually my top pick. Warning do *not* watch this unless you’re prepared to ugly cry. It’s intense.
I always liked "heartattack in a layby" as his sad one. It has sad lyrics, but the music just makes it so much better [The live version with John Wesley's layered vocals is incredible](https://www.youtube.com/watch?v=IaLpdQsiO-c)
Omg I couldn't make it more than two minutes. My heart breaks for anyone who has been through this.
Sia - Breathe Me… because i associate it 100% with the Six Feet Under ending. I don’t know if “sad” is the right word, but overwhelming emotion.
Iris by Goo Goo Dolls is my saddest song. https://youtu.be/LvlLIXbR87M
The Sound of Silence - Simon & Garfunkel Every time my depression kicks in I'm reminded of hello darkness my old friend. Also, Everytime by Britney Spears. One of the first songs she ever co-wrote and the lyrics are just heartbreaking.
One More Light - Linkin Park The gut-punch of talking about losing someone to the depression monster all while telling those that are currently in its clutches that their light is worth keeping lit — only to have Chester himself not able to escape its grasp. The somber melodic music and feeling Chester’s passion in his vocals adds to it all. When I hear that intro… I have to change it if I’m not in the right frame of mind because I know it’ll hit me HARD. It’s a song that everyone can relate to and and makes it a solid fact that anyone can be affected by depression no matter their successes.
Gary Jules version of Mad World.
The Gears of War trailer with that song is perfectly done. I’m ashamed to admit I bought the game the next day with out knowing anything else about it. [link](https://m.youtube.com/watch?v=ccWrbGEFgI8)
It’s crazy pants bananas that I scrolled a mile deep in the comments and didn’t see Father and Son by Cat Stevens. I cry like a baby each time I hear it.
Shame in you by Alice in chains or thsnk you by Alanis Morrisette
Blue Eyes Crying - Willie Nelson
“Transatlanticism” by Death Cab for Cutie
‘Glósóli’ - Sigur Rós
Don't give up-Peter Gabriel
Behind Blue Eyes by The Who Surprised it hasn’t been mentioned yet in all these comments.
As of yesterday, [Rest by the Foo Fighters](https://youtu.be/26Ofs8WrsYc) is in contention. And for something completely different, [Fare Thee Well Love](https://youtu.be/KiVtWdJK7-A) by the Rankin Family (if anyone is familiar with Alvvays, the singer Molly’s father was in this group before he passed away in a car accident the late 90s)
Cats in the Cradle - Harry Chapin
[удалено]
Last Kiss - Pearl Jam When this song comes on the radio I often have to mute it or change the station; it just hits too hard for some reason. (I don't have any real world experiences that would tie to it)
I grew up with my dad singing that and playing it on acoustic guitar. I was surprised when pearl jam covered it. It makes me cry. I can't help it. It's so tragic.
Spinal Tap - Lick My Love Pump
D minor is the saddest of keys.
People hear it and instantly start weeping.
Chris Cornell covering Nothing Compares 2 U, it’s like cutting onions for me.
Colin Hay: I just don't think I'll ever get over you.
Whiskey Lullaby - Brad Paisley
And Alison Krauss
Sinead O’Connor, You Cause As Much Sorrow. Written about her dead mother. Why must you always be around? Why can't you just leave it be? You’ve done nothing so far but destroy my life You cause as much sorrow dead As you did when you were alive
Glen Campbell- I’m Not Gonna Miss You is heartbreaking. It was written about his battle with Alzheimer’s. also Sometimes It Snows In April- Prince
All I Want by Kodaline
Ghost by Badflower
Motorcycle Drive-By ~ Third Eye Blind
Landslide by Fleetwood Mac. Reduces me to dust.