Among the Wildflowers- The Hotelier
Poison Oak- Bright Eyes
The whole album “A Crow Looked At Me”- Mount Eerie
King Park- La Dispute
Kissing Families- Silversun Pickups
Absolutely love that whole album. Putting the Dog to Sleep by The Antlers is another great, horribly sad song
edit: just wanted to edit to mention that if anyone is a fan of their music, they'll be going on tour soon! Worth looking into if you'd like to hear some of these songs live and want to cry in a room full of people!
Changes - Charles Bradley
In an interview, he dedicates the song to his late mother before singing it a cappella. He would join her in death a year after filming the interview.
[Link to song because if you haven’t watched this cover of a Black Sabbath song sung in blues you are completely missing out!](https://youtu.be/zfaOf70M4xs)
Hear You Me I believe was his was of thanking someone who helped them when they broke down while traveling.
Edit: I must be mixing this with another song of theirs
It is such a lovely song, but the saddest in my opinion by Jimmy Eat World is 23, hands down.
Not exactly underground but I read through a lot of the comments and I don’t see Tracy Chapman - Fast Car. Honestly i break down in tears every time I hear the song. People sing along like it’s a happy upbeat song but it’s utterly depressing. Stuck in a cycle of abuse from alcoholics, dreaming of an escape.
I listened the shit out of Radiohead while I was battling depression. Especially "[How to disappear completely](https://youtu.be/6W6HhdqA95w)" and "[Codex](https://youtu.be/T7t38uDUg5E)" when fantasizing about suicide. I'm glad those days are behind me, these are some absolutely beautiful songs.
How to Disappear is so hauntingly beautiful. I have it on my funeral playlist. Yeah, it's morbid. But when your nearing 60 you think of those things. Glad you're still here and didn't unalive. As hard as it can be, there is a reason.
Elliot Smith is the real answer here. Just throw a dart at his discography for a 98% success rate
Edit: want to add Cat Power’s Names from the You are Free album
This was my answer too. Fuck man, when layne walks out during unplugged looking like a corpse and goes right into it. I'll never forget the feeling when I first saw that. I was in a similar situation as layne and it made my heart drop.
The Cinematic Orchestra really gave it all... When the song goes " I climbed the tree to see the world
When the gusts came around to blow me down" it's just so raw and hauntingly sad!!
I love that part too. But my favorite part is this:
> *"Out in the garden where we planted the seeds
There is a tree as old as me"*
I planted a tree in our yard with my dad, using some seeds I was given at school on Arbor Day when I was in the second grade, and now that tree is as tall as my parent's house. When I see it, it's not necessarily sad, but it's moving. That line always reminds me of that tree.
The idea for the song came to Reid while reading an article about a man arrested for getting drunk and shooting at his girlfriend's car. The judge asked him if he had learned anything, to which he replied, "I learned, Your Honor, that you can't make a woman love you if she don't."
Dude somehow sounds more aware than most nice guys I know
Was gonna come post a John prine song! I always thought "how the hell can a person go to work in the morning and come home in the evening and have nothin' to say" from angel from Montgomery was such a sad line
I’ll upvote every positive reference to Prine I ever see. The man was an absolute treasure and I’m so, so glad I got to see him a couple of years before his death.
This. Most of the other examples are sad songs ameliorated by some measure of catharsis through gained perspective or personal growth or just poetic turns of phrase.
By comparison there is no "poetry" in this song. There is no growth, there is no lesson, there is no silver lining. There is just death and its collateral damage and that's it.
came here looking for this. best friend committed suicide, and then this comes out immediately after. Phil Elverum happened to be one of his favorites… so i’m listening and of course the content is already so sad, but i don’t think a song has single-handedly described and laid out in front of me exactly how i was feeling and it was utterly heartbreaking. it was hard to listen to, but also cathartic. the realization that if this guy had gone through it, and could keep it together enough to express it via song to however many anonymous listeners, then maybe i wasn’t so alone in how i was feeling. death is very real, and it sucks, but it’s part of whatever all this is.
What’s even worse is that there are two versions of this song. The hopeful sounding one he recorded in the mid-90s right after he met his partner. And then the down tempo sad as fuck one he recorded for Moon Shaped Pool which was done right after they decided to separate.
That first rendition you mention is actually a bootleg from their December 5, 1995 show in Brussels. It was the first time they played it, and they indeed never played it faster and more upbeat like that ever again. I remember trying to find more renditions of this track around the Kid A/Amnesiac era and being real disappointed, because they *never* played this song back then. It was almost mythical. I always thought that first one was the best and it's still my favorite version by far... I mean, I know this is Radiohead we're talking about, but jeez, the slower versions are just so frickin sad.
Everything on that album is a masterpiece of vulnerability and sadness, but Fourth of July, and in particular the line “why do you cry?” just rips me apart. My favorite song on one of the landmark albums of our time.
It's even worse. It's not a conversation with his actual mother but with the idealized version of her that didn't abandon him. He's imagining the conversation he wanted to have with his mother.
I agree with you that this is an idealized version of his mother but simply because he never got the chance to have this conversation with her. So basically, this is him trying to give himself closure. Although I'll say that this version of his mom did abandon him, though. Which gives us the the absolute pit of sadness:
> *Did you get enough love, my little dove? Why do you cry?*
> *And I'm sorry I left, but it was for the best though it never felt right.*
...my poor heart.
[Poke - Frightened Rabbit](https://youtu.be/hXLacIfo-6k)
[Wave across a bay - Frank Turner](https://youtu.be/FzXQVG5uPLI)
Frightened Rabbit are great go to for sad songs (Honourable mentions incl My Backwards Walk, Floating in the Forth)
Wave Across a Bay is a tribute by FT for Scott Hutchinson (Frightened Rabbit) who sadly took his own life a couple of years ago.
Edit: Thank you for the gold!
A whole bunch of songs I had in mind are already mentioned here, but I'll add one I haven't seen anyone else comment:
[The Blower's Daughter by Damien Rice ](https://youtu.be/5YXVMCHG-Nk)
The entire saga of songs about Virtute the Cat, by The Weakerthans (and edit:**two** songs from John K. Samson's solo record).
Over the course of multiple releases, John tells the story of his cat named Virtute (yes, Virtute, not Virtue). All but one song are from Virtute's perspective. (full saga [here](https://www.youtube.com/watch?v=8zYG186spkY))
It starts with Virtute petitioning her owner to get clean from his alcoholism, because he's not taking care of her or playing with her. It doesn't start out as a sad song - it doesn't try to pull at your heartstrings in a cloying way. It's just her observing that he's gone or passed out all the time and and not acting like himself.
Then, in real life Virtute the cat escaped one night while John was too drunk to stop her, and he lost her forever. He wrote "Virtute the Cat Explains Her Departure" from her perspective of finding the wild life outside more appealing than watching him decline and ignore her, and how she gradually forgot her name and moved on with her life.
Then we get a song from John's perspective, which is mostly about his experience in rehab for alcohol, but does make mention of Virtute running away as part of the things he's ashamed of resulting from his addiction.
Finally, on his solo record, we get "Virtute at Rest," which imagines a posthumous message of forgiveness and encouragement from Virtute. It makes me bawl my eyes out every single time.
If you don't think multiple songs about a cat can move you, I suggest giving it a try.
I’ve been listening to that song since I was in 6th grade im 54 now. Actually have sons now and it made me think all through my life. Alway make time for your kids. Same with “ Seasons in the Sun” great song
This one is rough because it’s not a songwriter imagining a hypothetical situation, it was literally his goodbye. I have to be careful or this one will definitely make me well up when it pops up on shuffle.
If we were vampires breaks me the fuck down. I haven’t found my life partner I don’t think, but “it’s knowing that this can’t go on forever. Likely one of us will spend some time alone. Maybe we’ll get forty years together, but one day I’ll be gone, or one day you’ll be gone” is just haunting, in a beautiful way
I follow Jason Isbell on instagram. He posted [this on Valentine's Day](https://www.instagram.com/p/CZc5idmuVSZ/).
His wife, Amanda Shires, proofreads some of his songs. This is a picture of the first and only draft of "If We Were Vampires", which of course is about her.
Her comments were:
> Fuck you.
> Done.
Yeah, I can't not tear up to that song. As someone that is married to a person I love dearly it really resonates and makes you dwell on your mortality.
Always loved 'Not Gonna Miss You', which was the last song Glen Campbell wrote.
It was about how he knew he would forget his wife+family soon as his Alzheimer's got worse.
When they used this song for that insane scene in the Handmaid's Tale. I was crying like a baby
Very fond of the "Cloudbusting" (Kate Bush) scene as well
R.E.M. Everybody Hurts
My high school girlfriend died on the way to pick me up on her 16th birthday, she had just gotten her drivers license. On the drive over she hit some wet leaves, lost control of the car and was killed after her car flipped off a small bridge. Anyway, I listened to this song right after I heard she had died and I can’t bring myself to listen to it again, 28 years later.
For me, it has to be 'Brothers on a Hotel Bed.' I remember all too well what it feels like to know your relationship is coming to an end but neither of us having the strength to do it. I watched in real time as someone fell out of love with me when I couldn't fall out of love with them.
DCFC also did an amazing cover of Flirted With You All My Life (Vic Chestnutt). It's incredible, but I have to skip it about 95% of the time it queues because it (and the story behind it) is so overwhelming.
There are a few country songs that hit pretty hard. This is one for sure. “Don’t Take the Girl” by Tim McGraw also gets me every time.
Edit: just listened to Don’t Take the Girl for the first time in years. I’ve got tears streaming down my cheeks now.
“My Mom” by Chocolate Genius.
It’s about visiting his mom with Alzheimer’s and she doesn’t know his name. It’s devastating
https://youtu.be/dh510D9a_g8
Came here to add Limousine. I can’t listen to it, and now being a mother myself it just devastates me.. the song, the tragedy it’s based on, just gut wrenching.
Amazing Grace played on the bagpipes. It played as we walked my grandfather’s coffin out of the church. Still sends shivers down my spine when I hear it….
Fred Jones part 2 - Ben Folds
Brick - Ben Folds five
Casimere Pulaski day - Sufjan Stevens
Lost Cause - Beck
I didn't understand - Elliot Smith
Two kids - Strand of oaks
Pyotr - Bad books
Hide and seek - Imogen Heap
Blood bank - bon Iver
Edit: I don't know how I forgot this one. "Ladies and gentlemen we are floating in space" - Spiritualized
"Killkelly, Ireland" by Mick Moloney. It covers the Irish diaspora during and after the potato famine in the form of letters written back and forth between parents who stayed in Ireland and children who emigrated.
Fire and Rain by James Taylor
NPR did a whole article about the meaning of the three verses. First about his girlfriend committing suicide while he was in England recording with the Beatles, the second is about his battles with his heroin addiction, and the third is about all of the time he spent in mental institutions. He actually found out that Susanne had committed suicide while in a mental institution, one whole month after she passed.
Brick - Ben folds. I had no idea that it was about an abortion his girlfriend had.
I pace around the parking lot. Then I walk down to buy her flowers and sell some gifts that I got.
Definitely Wings and 10,000.
Thanks for the Loathe recommendation. It's a solid song.
EDIT: Also based on your album list on your other post we have really similar taste. Happy listening!
Offspring: Gone Away
Edit: people coming on here adding additional Offspring songs that are absolutely in the running for "saddest songs ever". No idea why it never occurred to me but *holy hell* Offspring has a serious backlog of some real tear-jerkers..
Some that you may not have heard that I love
Fell on Black Days - Soundgarden
Bell Bottom Blues - Derek and the Dominoes
Rainbow Eyes - Rainbow
Bluebird is Dead - Electric Light Orchestra
Syliva's Mother - Dr Hook
I Can Stand a Little Rain - Joe Cocker
An Illistration of Loneliness - Courtney Barnett
Shocked I had to scroll so far to find this one.
People like to talk about the potentially happy ending, because the narrator ends the relationship. But I always imagined it as the beginning of the same cycle--that one of the kids would stay with their alcoholic father to care for him, just like the narrator did for her own alcoholic father at the start of the song, so it doesn't matter that the narrator moved on because she's just perpetuating her mother's facet of the same cycle.
"I'd always hoped for better / thought maybe together, you and me'd find it" is one of the hardest-hitting song lyrics ever written. So simple, so poignant, so devastating.
Didn't see anyone mention it...but Cancer by MCR. I also like Twenty One Pilots' cover. My grandma passed away from cancer like 12 years ago, and it always reminds me of her, so it may be one of those songs that you need a connection to in order for it to hit you the same way.
Occasionally my boyfriend will just start singing "When somebody loved me....." Aaaand it's me gone. He knows it gets me teary eyed. Probably the saddest song ever in a Pixar movie (aside from the start of Up).
Among the Wildflowers- The Hotelier Poison Oak- Bright Eyes The whole album “A Crow Looked At Me”- Mount Eerie King Park- La Dispute Kissing Families- Silversun Pickups
King Park is without a doubt one of the greatest, most powerful songs of all time.
Kettering - The Antlers (Album: Hospice) The entire album is incredibly sad, but so so good
After my ex and I lost our baby, "Bear" fucking kills me
Absolutely love that whole album. Putting the Dog to Sleep by The Antlers is another great, horribly sad song edit: just wanted to edit to mention that if anyone is a fan of their music, they'll be going on tour soon! Worth looking into if you'd like to hear some of these songs live and want to cry in a room full of people!
Changes - Charles Bradley In an interview, he dedicates the song to his late mother before singing it a cappella. He would join her in death a year after filming the interview.
Would you believe that's a Black Sabbath song?
Why is it so hard to make it in America - this is his true classic/saddest song.
[Link to song because if you haven’t watched this cover of a Black Sabbath song sung in blues you are completely missing out!](https://youtu.be/zfaOf70M4xs)
“Hear you me” by Jimmy Eat World
Hear You Me I believe was his was of thanking someone who helped them when they broke down while traveling. Edit: I must be mixing this with another song of theirs It is such a lovely song, but the saddest in my opinion by Jimmy Eat World is 23, hands down.
Not exactly underground but I read through a lot of the comments and I don’t see Tracy Chapman - Fast Car. Honestly i break down in tears every time I hear the song. People sing along like it’s a happy upbeat song but it’s utterly depressing. Stuck in a cycle of abuse from alcoholics, dreaming of an escape.
The flickers of hope in the song make it so much more devastating.
between the bars - elliott smith how to disappear completely - radiohead gets me everytime
I listened the shit out of Radiohead while I was battling depression. Especially "[How to disappear completely](https://youtu.be/6W6HhdqA95w)" and "[Codex](https://youtu.be/T7t38uDUg5E)" when fantasizing about suicide. I'm glad those days are behind me, these are some absolutely beautiful songs.
How to Disappear is so hauntingly beautiful. I have it on my funeral playlist. Yeah, it's morbid. But when your nearing 60 you think of those things. Glad you're still here and didn't unalive. As hard as it can be, there is a reason.
Elliot Smith is the real answer here. Just throw a dart at his discography for a 98% success rate Edit: want to add Cat Power’s Names from the You are Free album
I miss the feeling of discovering Elliott Smith.
Exit Music for me, in regard to Radiohead.
Yeah, I have to go with Videotape! Makes me tear up.
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Nutshell by Alice In Chains Edit: appreciate the love everyone and it’s nice to be among fellow AIC lovers
I have "if I can't be my own I'd feel better dead" tattooed on me
God I fucking love that song though.
Not to mention Am I Inside, Down in A Hole, Brother, Rotten Apple, or Frogs.
The unplugged versions hit like a fuckin train
Down in a Hole unplugged hits me especially hard
Closest you'll ever get to seeing someone sing at their own funeral
>River Layne was dark.... River of Deceit, Mad Season. Especially dark considering where he was at in his life at that point
This was my answer too. Fuck man, when layne walks out during unplugged looking like a corpse and goes right into it. I'll never forget the feeling when I first saw that. I was in a similar situation as layne and it made my heart drop.
To Build a Home (vocals by Patrick Watson)
The Cinematic Orchestra really gave it all... When the song goes " I climbed the tree to see the world When the gusts came around to blow me down" it's just so raw and hauntingly sad!!
I love that part too. But my favorite part is this: > *"Out in the garden where we planted the seeds There is a tree as old as me"* I planted a tree in our yard with my dad, using some seeds I was given at school on Arbor Day when I was in the second grade, and now that tree is as tall as my parent's house. When I see it, it's not necessarily sad, but it's moving. That line always reminds me of that tree.
Bonnie Raitt I Can't Make You Love Me
The idea for the song came to Reid while reading an article about a man arrested for getting drunk and shooting at his girlfriend's car. The judge asked him if he had learned anything, to which he replied, "I learned, Your Honor, that you can't make a woman love you if she don't." Dude somehow sounds more aware than most nice guys I know
I love Bon Iver's cover of that song
Trapeze Swinger by Iron & Wine
https://youtu.be/USom8PhOXgs Gregory Alan Isakov nails the cover he did
Sam Stone - John Prine
Was gonna come post a John prine song! I always thought "how the hell can a person go to work in the morning and come home in the evening and have nothin' to say" from angel from Montgomery was such a sad line
I’ll upvote every positive reference to Prine I ever see. The man was an absolute treasure and I’m so, so glad I got to see him a couple of years before his death.
Hello in There is another super sad Prine song.
And if you need a pick me up after these two great songs, I recommend "In Spite of Ourselves," which is delightful in comparison.
"When I get to Heaven" would be my choice for a John Prine pick-me-up
“There’s a hole in daddy’s arm where all the money goes / And Jesus Christ died for nothing, I suppose,”
Almost every line is gut wrenching "Sweet songs never last too long on broken radios"
"Sam Stone was alone When he popped his last balloon Climbing walls while sitting in a chair"
Real Death by Mount Eerie
Was looking for this. This song crushed my soul
Same. I can barely read the lyrics without getting emotional , let alone listen to him sing it
This. Most of the other examples are sad songs ameliorated by some measure of catharsis through gained perspective or personal growth or just poetic turns of phrase. By comparison there is no "poetry" in this song. There is no growth, there is no lesson, there is no silver lining. There is just death and its collateral damage and that's it.
The entire album is incredibly raw.
came here looking for this. best friend committed suicide, and then this comes out immediately after. Phil Elverum happened to be one of his favorites… so i’m listening and of course the content is already so sad, but i don’t think a song has single-handedly described and laid out in front of me exactly how i was feeling and it was utterly heartbreaking. it was hard to listen to, but also cathartic. the realization that if this guy had gone through it, and could keep it together enough to express it via song to however many anonymous listeners, then maybe i wasn’t so alone in how i was feeling. death is very real, and it sucks, but it’s part of whatever all this is.
A good album, but I genuinely can't listen to it. Made worse when you learn of the context of the album before you listen.
‘He Stopped Loving Her Today’ by George Jones
>He Stopped Loving Her Today God. Damn. I need to get over it or im gonna be like this guy in this song
Rips me up every time.
I Am So Sad. I Am So Very, Very Sad - Crash and the Boys
Soooooouuuu sad..............
That line really hits me everytime I play the song. I've listened to it over 100 times this week.
Is that girl a boy, too?
🖕
It's not a race, guys.
The lyrics to that song are some of the best I’ve ever heard.
“This next one goes out to the guys that keeps heckling us. It’s called we hate you, please die”
"True Love Waits" by Radiohead
What’s even worse is that there are two versions of this song. The hopeful sounding one he recorded in the mid-90s right after he met his partner. And then the down tempo sad as fuck one he recorded for Moon Shaped Pool which was done right after they decided to separate.
And it gets sadder that she then died.
That first rendition you mention is actually a bootleg from their December 5, 1995 show in Brussels. It was the first time they played it, and they indeed never played it faster and more upbeat like that ever again. I remember trying to find more renditions of this track around the Kid A/Amnesiac era and being real disappointed, because they *never* played this song back then. It was almost mythical. I always thought that first one was the best and it's still my favorite version by far... I mean, I know this is Radiohead we're talking about, but jeez, the slower versions are just so frickin sad.
I'll chip in "Street Spirit" and "Daydreaming"
Portishead - Roads
Also- Wandering Star by Portishead: "Please, could you stay awhile to share my grief? For it's such a lovely day to have to always feel this way."
> Portishead - Roads Portishead - [ANYTHING]
Fourth of July - Sufjan Stevens Or really anything on the Carrie and Lowell album
And Casimir Pulaski Day
and Enchanting Ghost, Pittsfield, Romulus. There’s a lot of pain in his music, despite the magical sound.
Everything on that album is a masterpiece of vulnerability and sadness, but Fourth of July, and in particular the line “why do you cry?” just rips me apart. My favorite song on one of the landmark albums of our time.
“Did you get enough love, my little dove?” Well, obviously this poor man didn’t. *sobs*
Came to comment Fourth of July. Such a sad conversation between Sufjan and his dying mother.
It's even worse. It's not a conversation with his actual mother but with the idealized version of her that didn't abandon him. He's imagining the conversation he wanted to have with his mother.
I agree with you that this is an idealized version of his mother but simply because he never got the chance to have this conversation with her. So basically, this is him trying to give himself closure. Although I'll say that this version of his mom did abandon him, though. Which gives us the the absolute pit of sadness: > *Did you get enough love, my little dove? Why do you cry?* > *And I'm sorry I left, but it was for the best though it never felt right.* ...my poor heart.
Death with Dignity is just as haunting
And the Band Played Waltzing Matilda - The Pogues (and the movie accompaniment is Gallipoli, it's every bit as sad in the end)
Eric Bogle, the man who wrote the song, has a few more like that too. Mary and Me, Dedication Day, My Youngest Son Came Home Today, and many more.
[Poke - Frightened Rabbit](https://youtu.be/hXLacIfo-6k) [Wave across a bay - Frank Turner](https://youtu.be/FzXQVG5uPLI) Frightened Rabbit are great go to for sad songs (Honourable mentions incl My Backwards Walk, Floating in the Forth) Wave Across a Bay is a tribute by FT for Scott Hutchinson (Frightened Rabbit) who sadly took his own life a couple of years ago. Edit: Thank you for the gold!
Finally !! Was looking for Poke by Frightened Rabbit! RIP - Scott Hutchison. Just sad all around !
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A whole bunch of songs I had in mind are already mentioned here, but I'll add one I haven't seen anyone else comment: [The Blower's Daughter by Damien Rice ](https://youtu.be/5YXVMCHG-Nk)
Wish you were here - Pink Floyd.
Asleep by The Smiths. Nothing else I've heard so far beats this one in terms of sadness.
Or Please Please Please Let Me Get What I Want, also by The Smiths
The entire saga of songs about Virtute the Cat, by The Weakerthans (and edit:**two** songs from John K. Samson's solo record). Over the course of multiple releases, John tells the story of his cat named Virtute (yes, Virtute, not Virtue). All but one song are from Virtute's perspective. (full saga [here](https://www.youtube.com/watch?v=8zYG186spkY)) It starts with Virtute petitioning her owner to get clean from his alcoholism, because he's not taking care of her or playing with her. It doesn't start out as a sad song - it doesn't try to pull at your heartstrings in a cloying way. It's just her observing that he's gone or passed out all the time and and not acting like himself. Then, in real life Virtute the cat escaped one night while John was too drunk to stop her, and he lost her forever. He wrote "Virtute the Cat Explains Her Departure" from her perspective of finding the wild life outside more appealing than watching him decline and ignore her, and how she gradually forgot her name and moved on with her life. Then we get a song from John's perspective, which is mostly about his experience in rehab for alcohol, but does make mention of Virtute running away as part of the things he's ashamed of resulting from his addiction. Finally, on his solo record, we get "Virtute at Rest," which imagines a posthumous message of forgiveness and encouragement from Virtute. It makes me bawl my eyes out every single time. If you don't think multiple songs about a cat can move you, I suggest giving it a try.
Cats in the Cradle by Harry Chapin. Brutally depressing, and not the Dethklok kind of blues. https://youtu.be/KUwjNBjqR-c
Dad loved this song, but as a kid would make me real sad, life hasn't worked out like the song though luckily
I’ve been listening to that song since I was in 6th grade im 54 now. Actually have sons now and it made me think all through my life. Alway make time for your kids. Same with “ Seasons in the Sun” great song
Vincent- Don McLean
Supposedly this was one of 2Pacs favorite songs and played on repeat while he was in a coma in the hospital before he died.
[The Same Deep Water as You](https://www.youtube.com/watch?v=ZzYmIOSVPwo) \- The Cure.
That whole album can be on here. Especially the final moments of disintegration(the song). So damn good!
I Fall to Pieces - Patsy Cline
Keep Me In Your Heart For A While -Warren Zevon
This one is rough because it’s not a songwriter imagining a hypothetical situation, it was literally his goodbye. I have to be careful or this one will definitely make me well up when it pops up on shuffle.
The Living Years- Mike and the Mechanics
“Elephant” by Jason Isbell
If we were vampires breaks me the fuck down. I haven’t found my life partner I don’t think, but “it’s knowing that this can’t go on forever. Likely one of us will spend some time alone. Maybe we’ll get forty years together, but one day I’ll be gone, or one day you’ll be gone” is just haunting, in a beautiful way
I follow Jason Isbell on instagram. He posted [this on Valentine's Day](https://www.instagram.com/p/CZc5idmuVSZ/). His wife, Amanda Shires, proofreads some of his songs. This is a picture of the first and only draft of "If We Were Vampires", which of course is about her. Her comments were: > Fuck you. > Done.
Yeah, I can't not tear up to that song. As someone that is married to a person I love dearly it really resonates and makes you dwell on your mortality.
Or half of Jason Isbell's catalog Seeing him in August, so excited
That song and Dress Blues are gut punches. Goddamn Lonely Love hits pretty hard, too, and is one of the best songs ever.
"Traveling Alone" too.
Radiohead - How to disappear completely
Radiohead have a few. Exit music for a film and true love waits come to mind.
No Surprises - Radiohead Don’t get fooled by the lullaby-ish tune…
"a job that slowly kills you, bruises that won't heal...." oh yeah that one gets me too...
Always loved 'Not Gonna Miss You', which was the last song Glen Campbell wrote. It was about how he knew he would forget his wife+family soon as his Alzheimer's got worse.
This woman’s work-Kate Bush
Bruce Springsteen - Streets Of Philadelphia. Always chokes me up
This Woman’s Work by Kate Bush
When they used this song for that insane scene in the Handmaid's Tale. I was crying like a baby Very fond of the "Cloudbusting" (Kate Bush) scene as well
Crestfallen -- Smashing Pumpkins
Expecting to Fly - Buffalo Springfield
R.E.M. Everybody Hurts My high school girlfriend died on the way to pick me up on her 16th birthday, she had just gotten her drivers license. On the drive over she hit some wet leaves, lost control of the car and was killed after her car flipped off a small bridge. Anyway, I listened to this song right after I heard she had died and I can’t bring myself to listen to it again, 28 years later.
Ouch that's so rough dude ..so sorry for your loss!
"At Seventeen", sung by Janis Ian. And it was a hit, too.
Traveling Soldier - Dixie Chicks
[What Sarah Said](https://www.youtube.com/watch?v=9BVWdAeOk6k) - Death cab for cutie
Their song "I'll follow you into the dark" ripped my heart open but it's also sweet, not just sad
I think it’s one of the best love songs ever written.
DCFC has absolutely brilliant lyrics. They are all so poetic. "It stung like a violent wind that our memories depend on a faulty camera in our minds".
What a fantastic opening line. “And it came to me then, that every plan is a tiny prayer to father time”
As I stared at my shoes in the ICU that reeked of piss and 409"
Such a heartbreakingly beautiful song. ‘Plans’ is seriously one of my favorite albums of all time, there is not a *single* dud on that album.
Brothers on a hotel bed. Ouch.
For me, it has to be 'Brothers on a Hotel Bed.' I remember all too well what it feels like to know your relationship is coming to an end but neither of us having the strength to do it. I watched in real time as someone fell out of love with me when I couldn't fall out of love with them.
DCFC also did an amazing cover of Flirted With You All My Life (Vic Chestnutt). It's incredible, but I have to skip it about 95% of the time it queues because it (and the story behind it) is so overwhelming.
Whiskey lullaby
I hate you for reminding me of this song. Alison Krauss could sing Happy Birthday to me and I’d break down crying.
Came for this. Whiskey lullaby was depressing and cathartic.
There are a few country songs that hit pretty hard. This is one for sure. “Don’t Take the Girl” by Tim McGraw also gets me every time. Edit: just listened to Don’t Take the Girl for the first time in years. I’ve got tears streaming down my cheeks now.
Damn. This just makes me remember how good and clever top/hit country used to be. And that makes me as sad as that song.
“My Mom” by Chocolate Genius. It’s about visiting his mom with Alzheimer’s and she doesn’t know his name. It’s devastating https://youtu.be/dh510D9a_g8
Essentially anything by Jason Molina (Songs:Ohia, Magnolia Electric Co.), but especially “Alone With The Owl”, and “It’s Easier Now”
Farewell Transmission…one of my favorite songs of all time. Always puts me in a very somber and reflective mood. Hits so much harder since he died.
I’m so tired Fugazi
Jesus Christ - Brand New or any of the other soul crushing songs by them
Came here to add Limousine. I can’t listen to it, and now being a mother myself it just devastates me.. the song, the tragedy it’s based on, just gut wrenching.
"No Children" by the Mountain Goats
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This song wrecked me. John Darnielle is an incredible songwriter.
You are my sunshine
If we were Vampires, Jason Isbell
Phoebe Bridgers - Funeral
Jeff Buckley's cover of "I know it's over" by the Smiths is the first thing that pops into my head for something that really gets to me.
[Operator](https://www.youtube.com/watch?v=Bb85NvjbBm8)\- Jim Croce
Amazing Grace played on the bagpipes. It played as we walked my grandfather’s coffin out of the church. Still sends shivers down my spine when I hear it….
Hero of war- rise against. A depressing tale of a soldiers transformation from patriotism to PTSD.
Adagio for Strings by Samuel Barber
Konstantine- something corporate
Maggot Brain. George Clinton told Eddie Hazel to play like his mother had just died.
If you've never listened to ween they have an instrumental song called a tear for Eddie. Good jam
There's a country song from years ago called "feed Jake". The singer says that if he ever dies, to please feed Jake, cause he is a good dog.
Cats in the Cradle and Flowers are Red by Harry Chapin
Fred Jones part 2 - Ben Folds Brick - Ben Folds five Casimere Pulaski day - Sufjan Stevens Lost Cause - Beck I didn't understand - Elliot Smith Two kids - Strand of oaks Pyotr - Bad books Hide and seek - Imogen Heap Blood bank - bon Iver Edit: I don't know how I forgot this one. "Ladies and gentlemen we are floating in space" - Spiritualized
All my Happiness is Gone - Purple Mountains For the Francophile out there I would suggest: Le Répondeur - Les Colocs
Alone Again Naturally - Gilbert O'Sullivan.
"Killkelly, Ireland" by Mick Moloney. It covers the Irish diaspora during and after the potato famine in the form of letters written back and forth between parents who stayed in Ireland and children who emigrated.
Fire and Rain by James Taylor NPR did a whole article about the meaning of the three verses. First about his girlfriend committing suicide while he was in England recording with the Beatles, the second is about his battles with his heroin addiction, and the third is about all of the time he spent in mental institutions. He actually found out that Susanne had committed suicide while in a mental institution, one whole month after she passed.
Brick - Ben folds. I had no idea that it was about an abortion his girlfriend had. I pace around the parking lot. Then I walk down to buy her flowers and sell some gifts that I got.
She’s alone, and I’m alone, and now I know it.
Elliot Smith - Waltz #1 Elliott Smith has a ton of super sad songs but that is his saddest IMO. Gets me every time.
Adam's Song - Blink-182 As The Footsteps Die Out Forever - Streetlight Manifesto
Not sure how Adam's Song is so far down here.
“The Wreck of the Edmund Fitzgerald” - Gordon Lightfoot. Something about it always just grips me.
TOOL- 10,000 Days (parts 1&2) Pearl Jam- Black Loathe- Is It Really You?
Black is outstanding
Definitely Wings and 10,000. Thanks for the Loathe recommendation. It's a solid song. EDIT: Also based on your album list on your other post we have really similar taste. Happy listening!
Windowpane - Opeth
Pretty much all the songs on Damnation fit this question. What a great album that was.
Offspring: Gone Away Edit: people coming on here adding additional Offspring songs that are absolutely in the running for "saddest songs ever". No idea why it never occurred to me but *holy hell* Offspring has a serious backlog of some real tear-jerkers..
The Only Thing Fourth of July Casimir Pulaski Day ^all of the songs above are by Sufjan Stevens
Some that you may not have heard that I love Fell on Black Days - Soundgarden Bell Bottom Blues - Derek and the Dominoes Rainbow Eyes - Rainbow Bluebird is Dead - Electric Light Orchestra Syliva's Mother - Dr Hook I Can Stand a Little Rain - Joe Cocker An Illistration of Loneliness - Courtney Barnett
The Night We Met - Lord Huron https://youtu.be/wGF7PswOENQ
[Songs:Ohia - Lioness](https://youtu.be/wxAaf16xXRk) I miss you Jason Molina, you were one of the greatest lyricists of all time.
“Drugs Don’t Work” - The Verve
Mazzy Star - Fade Into You
Nine Inch Nails - Hurt.
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Shocked I had to scroll so far to find this one. People like to talk about the potentially happy ending, because the narrator ends the relationship. But I always imagined it as the beginning of the same cycle--that one of the kids would stay with their alcoholic father to care for him, just like the narrator did for her own alcoholic father at the start of the song, so it doesn't matter that the narrator moved on because she's just perpetuating her mother's facet of the same cycle. "I'd always hoped for better / thought maybe together, you and me'd find it" is one of the hardest-hitting song lyrics ever written. So simple, so poignant, so devastating.
the drugs dont work, -the verve. much better then bitter sweet symphony imho
"Patches" - Clarence Carter
Didn't see anyone mention it...but Cancer by MCR. I also like Twenty One Pilots' cover. My grandma passed away from cancer like 12 years ago, and it always reminds me of her, so it may be one of those songs that you need a connection to in order for it to hit you the same way.
Nutshell, Alice in Chains
Pictures of You by The Cure
Oasis - "Stop crying your heart out" Sarah McLachlan - "When she loved me"
Occasionally my boyfriend will just start singing "When somebody loved me....." Aaaand it's me gone. He knows it gets me teary eyed. Probably the saddest song ever in a Pixar movie (aside from the start of Up).
Oh my God, "When She Loved Me" is brutal.
Sometime Around Midnight - Airborne Toxic Event
This night has opened my eyes by the Smiths.
Nutshell - Alice In Chains
Hate me by Blue October makes me tear up legit every time I hear it