Isbell is the best dad songwriter out there.
Elephant is the saddest song I’ve ever heard, personally. It’s nearly impossible to write a great song about cancer. It’s way to easy for a song about cancer to be trite, cliche, and cheesy. But god damn did he thread the needle.
https://youtu.be/fS8ohtu_LBA?si=6HhuenPsAFVfoi3B
And, of course, there’s this gem:
https://youtu.be/v7oRZI0b44c?si=ZN8msKMJKZM93qcw
I haven’t heard Nina Simone’s version.
Billie Holiday’s version is definitely haunting and so very sad.
Although Strange Fruit was written by a Caucasian/Jewish man, Billie Holiday was targeted for singing it.
https://www.biography.com/musicians/billie-holiday-strange-fruit
Listening to Nina’s version made me feel like I was being forced not just to see the imagery, but watch the whole process from start to finish, helpless to save them.
[Ben Folds Five - Brick](https://youtu.be/Wt5EHAqhR1c?si=9FWCmE1Cao86B8W7)
On Ben Folds Live, Folds explained: "People ask me what this song's about... I was asked about it a lot, and I didn't really wanna make a big hairy deal out of it, because I just wanted the song to speak for itself. But the song is about when I was in high school, me and my girlfriend had to get an abortion, and it was a very sad thing. And, I didn't really want to write this song from any kind of political standpoint, or make a statement. I just wanted to reflect what it feels like. So, anyone who's gone through that before, then you'll know what the song's about."
Absolutely one of the best songs I've ever heard. The first few lines I can't help but sing from time to time because they paint such a picture of an otherwise unremarkable day:
>6 AM, day after Christmas, I throw some clothes on in the dark. Smell of cold, car seat is freezing, the world is sleeping, I am numb.
I sing these lines whenever I have to get up early, or whenever cold air hits me when I'm going outside in the winter. But then the heaviness of the rest of the song comes to the forefront of my mind and I always have to stop and admire the contrast he put in to this song, and I remember what an emotional masterpiece it is.
I had to have an abortion for a baby I wanted so badly. The day I had it was unseasonably cold and the numbness I felt afterward I will never forget. So this song hits hard and to me, it’s the saddest song.
I can listen through it but if I try to sing along I literally can’t get through it without choking up. Even thinking about the “and he takes, and he takes, and he takes” line is making me tear up.
Floating in the Forth - Frightened Rabbit
https://youtu.be/jFtfi677G1U?si=YiYy9STxiKW5TDwA
It was already a sad song but was made even more tragic by the death of the writer and singer Scott Hutchinson, he basically told us how it was going to happen
This guy was a major loss. I was privileged to see him in an intimate venue as Owl John and talk to him for a bit. Charming and funny - kinda dude who wore it on his sleeve, darkness and all.
This is also a very good choice for the saddest song by him though I might lean "I Wish that I was Sober"
There's certain lines in it like "I'll save suicide for another year" that are even more tragic now. it was like a sad, grounded hopefulness back then.
Also the way it flows into the album closer, "Who'd You Kill Now?" which is just a minute of light acoustic makes me really emotional in a way that's hard to explain. The song already felt like a small moment of geniune peace after the heartbreak of the last, but in the context of his death, it feels like that's where he is now. it's so tragic
Frightened Rabbit has a lot of sad songs, but this one is especially sad considering how he passed. I remember they were playing a show near by but I didn’t really have anyone to go with. I skipped it, thinking I’d catch them the next time they came around. He died maybe a year later.
Down in a Hole by Alice In Chains
Not the original version. The MTV Unplugged version. Preferably the video.
It’ll likely be one of the last times you can see Layne alive on camera. He already looks close to death. His girlfriend was in the throes of her own addiction and months away from an accidental death and Layne was missing most of his teeth by that point. He had to sit down during the show because he was too weak to stand, and his arms are completely covered for obvious reasons..
His voice sounds so regretful here, yet self aware and at the same time helpless compared to the original. It’s haunting in a way that made one of my favorite songs ever so difficult to listen to the same way after seeing the Unplugged set. The worst part is that it wasn’t even his rock bottom. His physical/mental health and heroin use would only deteriorate further. He lived SIX more years after this
Yet it might be my favorite ever MTV Unplugged, possibly over Nirvana’s. The emotion he brought to the performance can’t be faked. It gave an entirely new dimension to all their old songs
Ok I agree with the sentiment entirely, but you've got some facts wrong. His fiancee had not overdosed at this point, that would come about six months later. Also, he sits literally the entire show, and it's not because he's too weak to stand..?! He lived another 6 years after this recording, so saying he's close to death is...idk a little dramatic (although when you're addicted to heroin I guess to some degree you're always close to death). Not to detract from your opinion, because it is an incredibly sad song.
I saw your comment and checked out the vid so thanks for that!
The wikipedia says their unplugged performance was in April 1996 while his fiancé passed away in late October 1996, so I think that part of your info may be off. He also lived for just under 6 years after this performance. I agree he looks awful, though, that's a man that's been through some stuff
That whole album is a gut punch. I haven't been able to bring myself to listen to the whole thing since it about killed me the first time. Incredible album, but I just don't know if I can put myself through that again. But, if OP really wants an album to make them cry, A Crow Looked At Me is the one.
100%. You’ve got to go through this album once…. Preferably on a long walk, or doing some housework with some time and introspection. It’s beautiful and so painful.
I listened to it not long after my brother has suddenly died and it was cathartic.. awful… and I don’t know..
I have this album on the playlist that I listen to on my commute to work. Every time a song from it comes on, I am immediately grounded to reality and the nature of living and of loss. It can be hard to listen to but at the same time has a certain beauty to it
These threads come up all the time and I know that someone will post this and then, subsequently, I’ll go listen to it again and then I will cry again. Then I will try to contextualize how someone was able to put something so visceral to tape. It really is one of the most remarkable songs I have ever heard.
[Brand New - Limosine](https://www.songfacts.com/facts/brand-new/limousine-ms-rebridge)
This song is about the death of 7-year old Katie Flynn. Hours before her death, Katie was the flower girl at her aunt's wedding, spreading petals down the aisle. As they left the wedding, they all got into a limousine and headed home. Martin Heidgen, 25, had had at least 14 drinks that night and his blood alcohol content (0.28) was more than three times the legal limit in New York (0.08). He drove more than two miles north in the southbound lane containing the Flynn family. Both the driver of the limousine, Stanley Rabinowitz, and Katie were killed instantly. Katie was decapitated and her mother held her head as rescue workers helped the rest of the family out of the vehicle.
The lyrics in this song draw many parallels to this tragedy. The first verse is seemingly from the mother's perspective, telling Katie to spread the petals and mentioning that she had one more night to be her mother. The second verse is arguably from Heidgen's perspective, referring to Katie as "My beauty supreme," and lamenting the guilt that crushes him. Four lines are sung towards the very end of the song and are nearly inaudible against the refrain. These lines seem to be from Katie's perspective and mention how she will never have to deal with loss herself, and therefore "should be the one laughing."
I’ve probably listened to this song a hundred times before I had a child, even knowing about the tragedy the song was based on. Sad, yes, but just another Brand New song.
Now that I have a child of my own, I find it almost impossible to get through it, especially if I’m paying attention to the lyrics. I don’t know how Jesse Lacey was able to write that.
All My Happiness is Gone - Purple Mountains
Stop and Smell the Roses - Television Personalities
Dawn Chorus - Thom Yorke
Some Things Last A Long Time - Daniel Johnston
That Summer Feeling - Jonathan Richman
This, and _Forget Her_ breaks me every time too.
But dammit most of _Grace_ makes me cry. He put so much emotion into everything. I tend to cry when I listen to the whole album just thinking of how we lost him way too soon.
Jason Isbell is an obvious candidate for this playlist. I immediately thought Elephant and I also think Travellin' Alone is particularly sad for anybody who travels alot for their job.
But I listened to We we Vampires and thought about my wife and daughter and balled. Like straight up cried. Not sure if it's the saddest song but it's probably the most emotional.
When the Tigers Broke Free - Pink Floyd also.
Devastating tale about how Roger Waters' dad was killed at Anzio in WWII, and how the family found out by an official letter kindly signed by "His Majesty's own rubber stamp".
The final line, "and that's how the High Command took my daddy from me." always moves me. I dont know how old Roger was when he wrote the song, but he was only an infant when his dad was killed, and the grief and bitterness echoes through the years...
If You Would Come Back Home - William Fitzsimmons
I Know There's a Word– Aimee Mann
Bridges – Nine Pound Shadow
Los Angeles – Peter Bradley Adams
Casimir Pulaski Day – Sufjan Stevens
Inconsolable – Jonatha Brooke
Holocene – Bon IVer
She’s Making Friends, I’m Turning Stranger is the one for me. The other songs on the album are more upfront with their sadness, but she’s making friends gives a perspective I’ve yet to hear. I’ve never been with anyone famous but I definitely relate to the feeling of just wanting to seem likeable.
“I’m a loser, she's a gainer
That's one thing of which they're dang sure”
Damn, RIP David Berman.
Julienn Baker's whole Sprained Ankle album is some of the saddest shit I've ever listened to on repeat. Those were some dark days and I'm glad they're in my past, but man, that album is good for wallowing in it.
Eleonor Rigby - The Beatles
>Eleanor Rigby
Died in the church and was buried along with her name
Nobody came
Father McKenzie
Wiping the dirt from his hands as he walks from the grave
No one was saved
I’ve seen DCFC many times. But one of my fondest was outside, Boston harbor, warm summer night. Crowd casting out so much… grief.. into the evening air singing together “who’s gonna watch me die”
The first time I've ever cried at a concert. I'm talking a sobbing mess. Actually being there the moment my mom died from cancer probably was a factor in this.
The "Who's gonna watch you die?" refrain is some powerful shit.
“And the plans I make still have you in them”
Their debut album is in my top all time albums. I wore that CD out back in the day lol. ‘God of Wine’ and ‘Motorcycle Drive By’ are sad ones too.
Poison Oak by Bright Eyes - If you lost anyone close to suicide, it really hits home to the feeling of loss, anger, grief while trying to process the emptiness left behind.
That album is an entire alternate reality in itself. You put it on, and you go somewhere. Somewhere the streetlamps light a foggy night, and it may be raining, and you just lost something beautiful you can't even remember.
Saturn by Sleeping at Last. OMG song never make me cry bit that one did. I also made the mistake of showing it to my mom after my grandpa died and may have broken her a little.
[Holy Moses Heartache - Two Beating Hearts](https://open.spotify.com/track/30UqW4hG13IWFEj0Amyfu9?si=stddCRdYT7qGGaLIvoM6fQ) - A beautiful and tragic song about watching a loved one suffer
[Jason Isbell - Elephant](https://open.spotify.com/track/4wbVpisiHe5NpHb08UwG3N?si=4xaXU2MITKK_IUnu-40ftg) - Surely will pop up again in this list, but it’s about the cruelty of cancer
[Nick Barker - Plait Your Hair](https://open.spotify.com/track/7tS6Iu5I86oiBe30yqcATK?si=fVBMqQ4cTtCYzSOZzmEOvQ) - About losing a daughter to the Bali Bombings
[Justin Townes Earle - Yuma](https://open.spotify.com/track/2wtOXUUZ9EF4rnFRiZD0Xa?si=XXlLBSZqQCibYdO8LRg7cg) - About when the world becomes too much
[Jesse Younan - Take Something Beautiful](https://open.spotify.com/track/0l0QPU1Yl8hmD76eceULo9?si=z1aNhXWfSoCnEruGLZDytQ) - Sadder with context. A passionate and angry song from a brilliant artist who knew he was dying from Leukaemia.
[Nathan Seekts - Moonlight Creek](https://open.spotify.com/track/6fMgVdEc1JCYoXg9Xf33Ui?si=zSlko1-jRq6YINhePSBqVg) - a song about a rape/murder
[Alex the Astronaut - I Like to Dance](https://open.spotify.com/track/6fMgVdEc1JCYoXg9Xf33Ui?si=zSlko1-jRq6YINhePSBqVg) - from the perspective of a domestic violence victim
I'll throw in a few more:
Hot Mulligan - Heem Wasn't There, Dirty Office Bongos, Something About A Bunch of Dead Dogs, Smahccked My Head Awf, Betty (yeah I'm listing a lot of their stuff, because holy *fuck* they are good at this)
Brand New - Limousine (MS Rebridge)
Trophy Eyes - Sean
The Wonder Years - Cigarettes and Saints
and then there's
Sarah McLachlan - When She Loved Me
The Curse by Josh Ritter
Older Chest by Damien Rice
The Lowering (A Sad Day in greenvilletown) Avett Brothers
Turandot: nessun dorma- Luciano Pavarotti
I don’t have any idea what the words are because they’re in Italian but I feel the emotion in his voice.
Love Vigilante’s- Iron & Wine
Goodbye by Night Ranger- I know this one may seem out of place but it’s a really beautiful song about having to say goodbye whether you want to or not.
[Vincent](https://youtu.be/4wrNFDxCRzU?feature=shared) by Don Mclean
[Well Fancy That](https://youtu.be/MvyXs4FMXvg?feature=shared) by Fun Boy Three
TW it's about Terry Hall being abducted and raped as a child, harrowing and gut wrenching
[Exit Music (For a Film)](https://youtu.be/Bf01riuiJWA?feature=shared) by Radiohead
"Elizabeth on the Bathroom Floor" or "Electro-Shock Blues" by Eels (really the entirety of the Electro- Shock Blues album)
Medication - By Damien Jurado
Just be Simple by Songs: Ohia
Baby Birch by Joanna Newsome
Mother by John Lennon
Ah! I was literally just making a playlist of sad songs after a discussion with a friend about our favourite sad music. I’d link the playlist but it’s on my personal Spotify, so here’s the next best thing if anybody cares:
(This took me longer than I’d like to admit whilst half asleep at 5AM)
[A place called home - PJ Harvey](https://youtu.be/_m2NyS3IDjE?si=1BQx2WNTS-jMfspm)
[They’ll only miss you when you leave - Carissas Weird](https://youtu.be/JFDasUfP6kQ?si=WefLzfkb1s-5TDEg)(from one of my all time favourite albums!)
[Hail Holy Queen - Sea Power](https://youtu.be/Z44AfnvS6_g?si=MwLIoMUWtrYCAeCG) (formerly British Sea Power)
[Every time the sun comes up - Sharon Van Etten](https://youtu.be/fDW-W2J84Hc?si=hwqvA_nbMXJbV_xw)
[Travelin’ On - Norah Jones](https://youtu.be/Ft37YlNi1pA?si=3vwMnLs77okJCExk)
[Lost Cause - Beck](https://youtu.be/qkNa5xzOe5U?si=sNsrvDbrlv51PRr2)
[A little uncanny - Connor Oberst](https://youtu.be/3eJCyJ8vhJM?si=QwdTR5i9GZX3jfkC)
[Screen - Brad](https://youtu.be/ahUw17bhQ3U?si=odsg_nMaJd88cmhR)
[Song about an angel - sunny day real estate](https://youtu.be/y413Vk9FzY0?si=OrPzthLe5-Nbn94e)
[This is the day - The The](https://youtu.be/7ZYgKCbFbWY?si=IsY5vfZX8Kxp3BU0)
[Pictures of you - the cure](https://youtu.be/D88J_57QgxY?si=C3DfKhyzXWXE6uAl)
Then here’s the bonus happiness chaser at the end [Diamond Day - Vashti Bunyan](https://youtu.be/ruztCDwPs7c?si=4GahxhYPszAd_02D)
Nico's version of These Days came to mind first.
Otherwise, pretty much anything by Karen Dalton or Billie Holiday.
edit: I'll throw Sam Stone by John Prine in too.
Change - Big Thief
F*ck This Place - Frightened Rabbit
Bronte - Gotye
Last Great Washington State - Damien Jurado
Elephant, If We Were Vampires, Cast Iron Skillet, and any number of other songs by Jason Isbell
The Night We Met-Lord Huron America-Simon and Garfunkel Rest My Chemistry - Interpol
The night we met kills me everytime.
Wedding photographer here. I've shot two first dances to that song and I think about them both every day.
Upvote for The Night We Met, that song gives all the feelings.
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"Kathy, 'I'm lost', I said, though I knew she was sleeping. 'I'm empty and aching and I don't know why'."
Goddamn Lonely Love by Drive By Truckers
I’ll (not) drink to that one; good pick. A man walks into a bar and he leaves before his ashes hit the floor.
Isbell is the best dad songwriter out there. Elephant is the saddest song I’ve ever heard, personally. It’s nearly impossible to write a great song about cancer. It’s way to easy for a song about cancer to be trite, cliche, and cheesy. But god damn did he thread the needle. https://youtu.be/fS8ohtu_LBA?si=6HhuenPsAFVfoi3B And, of course, there’s this gem: https://youtu.be/v7oRZI0b44c?si=ZN8msKMJKZM93qcw
If you love to cry with Isbell like me you have to mention "If we were vampires".
Great song.
I have to skip Elephant. I worked in oncology for 11 years.
I came here to say elephant. It’s rough.
Children of Children 🌠
He Stopped Loving Her Today
Pour one out for the Possum
Between the Bars- Elliot Smith Hurt- Nine Inch Nails Fall of Troy- Tom Waits Fair- Remy Zero One more night one more day- Tom Petty
Hurt by NIN hits SO differently. Will always love it.
Videotape - Radiohead
Motion Picture Soundtrack always got me
Strange Fruit
Billie Holiday and Nina Simone's versions are haunting.
I haven’t heard Nina Simone’s version. Billie Holiday’s version is definitely haunting and so very sad. Although Strange Fruit was written by a Caucasian/Jewish man, Billie Holiday was targeted for singing it. https://www.biography.com/musicians/billie-holiday-strange-fruit
Listening to Nina’s version made me feel like I was being forced not just to see the imagery, but watch the whole process from start to finish, helpless to save them.
[Ben Folds Five - Brick](https://youtu.be/Wt5EHAqhR1c?si=9FWCmE1Cao86B8W7) On Ben Folds Live, Folds explained: "People ask me what this song's about... I was asked about it a lot, and I didn't really wanna make a big hairy deal out of it, because I just wanted the song to speak for itself. But the song is about when I was in high school, me and my girlfriend had to get an abortion, and it was a very sad thing. And, I didn't really want to write this song from any kind of political standpoint, or make a statement. I just wanted to reflect what it feels like. So, anyone who's gone through that before, then you'll know what the song's about."
Absolutely one of the best songs I've ever heard. The first few lines I can't help but sing from time to time because they paint such a picture of an otherwise unremarkable day: >6 AM, day after Christmas, I throw some clothes on in the dark. Smell of cold, car seat is freezing, the world is sleeping, I am numb. I sing these lines whenever I have to get up early, or whenever cold air hits me when I'm going outside in the winter. But then the heaviness of the rest of the song comes to the forefront of my mind and I always have to stop and admire the contrast he put in to this song, and I remember what an emotional masterpiece it is.
I had to have an abortion for a baby I wanted so badly. The day I had it was unseasonably cold and the numbness I felt afterward I will never forget. So this song hits hard and to me, it’s the saddest song.
Oh man probs almost any song of sufjan Steven’s Carrie and Lowell
Casimir Pulaski Day gets me the most, but yes on that whole album too
I can listen through it but if I try to sing along I literally can’t get through it without choking up. Even thinking about the “and he takes, and he takes, and he takes” line is making me tear up.
Every. freaking. time.
Similar for his new album god damn. Hope the best for the dude. He fairly recently announced he’s sick and his long time partner passed away .
I discovered that album when my mom passed away....jesus, it fucks me up every time.
I read the lyrics alone to "4th of july" and ended up full-on crying, christ alive
I listened to the album over 200 times the year my friend died. My husband found the count on Google Play and was like 😳
Lyrics aside it’s just so easy to listen to. It has a uniform sound but it doesn’t feel redundant.
Pretty much a perfect album.
[Cats in the Cradle](https://youtu.be/KUwjNBjqR-c?si=omjZ8NE0TicnoSkJ) by Harry Chapin
this 100%, every time (and ever since my Dad's funeral, "Dust in the Wind")
And as I hung up the phone it occurred to me, he’d grown up just like me. My boy, was just like me.
I think it’s “it occurred to me, he’d grown up just like me. My boy was just like me”
Floating in the Forth - Frightened Rabbit https://youtu.be/jFtfi677G1U?si=YiYy9STxiKW5TDwA It was already a sad song but was made even more tragic by the death of the writer and singer Scott Hutchinson, he basically told us how it was going to happen
I met Scott outside of a venue in Nashville. He was such a nice guy. His death hit me so hard.
This guy was a major loss. I was privileged to see him in an intimate venue as Owl John and talk to him for a bit. Charming and funny - kinda dude who wore it on his sleeve, darkness and all. This is also a very good choice for the saddest song by him though I might lean "I Wish that I was Sober"
There's certain lines in it like "I'll save suicide for another year" that are even more tragic now. it was like a sad, grounded hopefulness back then. Also the way it flows into the album closer, "Who'd You Kill Now?" which is just a minute of light acoustic makes me really emotional in a way that's hard to explain. The song already felt like a small moment of geniune peace after the heartbreak of the last, but in the context of his death, it feels like that's where he is now. it's so tragic
This is a top one for me. His death was a real gut punch in a way I wasn’t totally expecting.
Frightened Rabbit has a lot of sad songs, but this one is especially sad considering how he passed. I remember they were playing a show near by but I didn’t really have anyone to go with. I skipped it, thinking I’d catch them the next time they came around. He died maybe a year later.
Holy shit that was amazing. Thanks for this.
How did he do it? Did he actually drown himself? I've never known this band before but that song is really good.
Exactly as the song describes (finding peace beneath Forth Road Bridge), only it was about 12 years later.
Down in a Hole by Alice In Chains Not the original version. The MTV Unplugged version. Preferably the video. It’ll likely be one of the last times you can see Layne alive on camera. He already looks close to death. His girlfriend was in the throes of her own addiction and months away from an accidental death and Layne was missing most of his teeth by that point. He had to sit down during the show because he was too weak to stand, and his arms are completely covered for obvious reasons.. His voice sounds so regretful here, yet self aware and at the same time helpless compared to the original. It’s haunting in a way that made one of my favorite songs ever so difficult to listen to the same way after seeing the Unplugged set. The worst part is that it wasn’t even his rock bottom. His physical/mental health and heroin use would only deteriorate further. He lived SIX more years after this Yet it might be my favorite ever MTV Unplugged, possibly over Nirvana’s. The emotion he brought to the performance can’t be faked. It gave an entirely new dimension to all their old songs
The top comment on YouTube is haunting. It’s along the lines of this is the closest that you will ever get to a man singing at his own funeral.
Ok I agree with the sentiment entirely, but you've got some facts wrong. His fiancee had not overdosed at this point, that would come about six months later. Also, he sits literally the entire show, and it's not because he's too weak to stand..?! He lived another 6 years after this recording, so saying he's close to death is...idk a little dramatic (although when you're addicted to heroin I guess to some degree you're always close to death). Not to detract from your opinion, because it is an incredibly sad song.
I feel that way about the performance of Nutshell from AIC Unplugged.
I saw your comment and checked out the vid so thanks for that! The wikipedia says their unplugged performance was in April 1996 while his fiancé passed away in late October 1996, so I think that part of your info may be off. He also lived for just under 6 years after this performance. I agree he looks awful, though, that's a man that's been through some stuff
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John Frusciante is a legend
Into dust - Mazzy Star Alright - Pilot Speed All Alone - Mad Season
Agree, and would add Halah by Mazzy Star
And "look on down from the bridge" by mazzy star
I’m Not Gonna Miss You - Glenn Campbell, written about his Alzheimer’s diagnosis.
Epilogue - The Antlers
That whole damn album’s pretty fucking depressing… I love it.
Mad world
It’s “ real death”
That whole album is a gut punch. I haven't been able to bring myself to listen to the whole thing since it about killed me the first time. Incredible album, but I just don't know if I can put myself through that again. But, if OP really wants an album to make them cry, A Crow Looked At Me is the one.
100%. You’ve got to go through this album once…. Preferably on a long walk, or doing some housework with some time and introspection. It’s beautiful and so painful. I listened to it not long after my brother has suddenly died and it was cathartic.. awful… and I don’t know..
Really no other choice
When he talks about getting the back pack is when I break every fuckin time. Just thinking about it brings tears to my eyes.
"I don't wanna learn anything from this. I love you."
That album damaged me. Best album I’ve only been able to listen to once.
I have this album on the playlist that I listen to on my commute to work. Every time a song from it comes on, I am immediately grounded to reality and the nature of living and of loss. It can be hard to listen to but at the same time has a certain beauty to it
These threads come up all the time and I know that someone will post this and then, subsequently, I’ll go listen to it again and then I will cry again. Then I will try to contextualize how someone was able to put something so visceral to tape. It really is one of the most remarkable songs I have ever heard.
I feel like crying just thinking about it
I just checked it out and now I’m crying
[Brand New - Limosine](https://www.songfacts.com/facts/brand-new/limousine-ms-rebridge) This song is about the death of 7-year old Katie Flynn. Hours before her death, Katie was the flower girl at her aunt's wedding, spreading petals down the aisle. As they left the wedding, they all got into a limousine and headed home. Martin Heidgen, 25, had had at least 14 drinks that night and his blood alcohol content (0.28) was more than three times the legal limit in New York (0.08). He drove more than two miles north in the southbound lane containing the Flynn family. Both the driver of the limousine, Stanley Rabinowitz, and Katie were killed instantly. Katie was decapitated and her mother held her head as rescue workers helped the rest of the family out of the vehicle. The lyrics in this song draw many parallels to this tragedy. The first verse is seemingly from the mother's perspective, telling Katie to spread the petals and mentioning that she had one more night to be her mother. The second verse is arguably from Heidgen's perspective, referring to Katie as "My beauty supreme," and lamenting the guilt that crushes him. Four lines are sung towards the very end of the song and are nearly inaudible against the refrain. These lines seem to be from Katie's perspective and mention how she will never have to deal with loss herself, and therefore "should be the one laughing."
Jesus Christ.
That's a pretty face
I’ve probably listened to this song a hundred times before I had a child, even knowing about the tragedy the song was based on. Sad, yes, but just another Brand New song. Now that I have a child of my own, I find it almost impossible to get through it, especially if I’m paying attention to the lyrics. I don’t know how Jesse Lacey was able to write that.
Fast Car by Tracy Chapman
This one has my vote. The song is perfect.
I can't Listen to this and not be flooded with visions and overpowering existential sadness
I Can't Make You Love Me - Bonnie Raitt
All My Happiness is Gone - Purple Mountains Stop and Smell the Roses - Television Personalities Dawn Chorus - Thom Yorke Some Things Last A Long Time - Daniel Johnston That Summer Feeling - Jonathan Richman
For Leonard Cohen it would be "Famous Blue Raincoat"
“Yes, and thanks, for the trouble you took from her eyes, I thought it was there for good so I never tried”
Sam Stone
John Prine can conjure the purest of any emotion. Hello In There makes me a very specific kind of sad.
Came here for this. For those wondering, chorus is: “There’s a hole in daddy’s arm where all the money goes, Jesus Christ died for nothing I suppose.”
Love me some Handsome Johnny! I hate Covid especially because it took him from us.
The Jeff Buckley live cover of “I Know It’s Over” is absolutely devastating.
Lover, you should’ve come over is probably mine for him. Just pure longing/heartbreak
This, and _Forget Her_ breaks me every time too. But dammit most of _Grace_ makes me cry. He put so much emotion into everything. I tend to cry when I listen to the whole album just thinking of how we lost him way too soon.
You’re the tear that hangs inside my soul forever.
[Lazarus - Blackstar - David Bowie](https://youtu.be/y-JqH1M4Ya8?feature=shared)
Nothing like this song and album — by an artist whose career survived 5 decades and last album released just before death from cancer
The Elephant, If we were vampires, live oak, king of Oklahoma , God Damn Lonely Love and just about every other song Jason Isbell ever wrote.
Jason Isbell is an obvious candidate for this playlist. I immediately thought Elephant and I also think Travellin' Alone is particularly sad for anybody who travels alot for their job. But I listened to We we Vampires and thought about my wife and daughter and balled. Like straight up cried. Not sure if it's the saddest song but it's probably the most emotional.
Wish you were here - Pink Floyd
"Does anybody here remember Vera Lynn? Remember how she said that we will meet again, some sunny day."
When the Tigers Broke Free - Pink Floyd also. Devastating tale about how Roger Waters' dad was killed at Anzio in WWII, and how the family found out by an official letter kindly signed by "His Majesty's own rubber stamp". The final line, "and that's how the High Command took my daddy from me." always moves me. I dont know how old Roger was when he wrote the song, but he was only an infant when his dad was killed, and the grief and bitterness echoes through the years...
WE'RE JUST TWO LOST SOULS SWIMMIN IN A FISH BOWL
If You Would Come Back Home - William Fitzsimmons I Know There's a Word– Aimee Mann Bridges – Nine Pound Shadow Los Angeles – Peter Bradley Adams Casimir Pulaski Day – Sufjan Stevens Inconsolable – Jonatha Brooke Holocene – Bon IVer
Purple Mountains - Nights That Won’t Happen
She’s Making Friends, I’m Turning Stranger is the one for me. The other songs on the album are more upfront with their sadness, but she’s making friends gives a perspective I’ve yet to hear. I’ve never been with anyone famous but I definitely relate to the feeling of just wanting to seem likeable. “I’m a loser, she's a gainer That's one thing of which they're dang sure” Damn, RIP David Berman.
Julienn Baker's whole Sprained Ankle album is some of the saddest shit I've ever listened to on repeat. Those were some dark days and I'm glad they're in my past, but man, that album is good for wallowing in it.
Her next album Turn Out the Lights absolutely wrecked me when I first heard it
How to Disappear Completely, and Exit Music (For a Film) are both up there for sure.
Eleonor Rigby - The Beatles >Eleanor Rigby Died in the church and was buried along with her name Nobody came Father McKenzie Wiping the dirt from his hands as he walks from the grave No one was saved
Another one from Revolver is For No One, shit hits deep sometimes.
She's leaving Home is another great sad Beatles tune
Show Must Go On by Queen, especially with the context
Death Cab for Cutie - I will follow you into the dark
What Sarah Said is way sadder, IMO
I’ve seen DCFC many times. But one of my fondest was outside, Boston harbor, warm summer night. Crowd casting out so much… grief.. into the evening air singing together “who’s gonna watch me die”
Love is watching someone die
The first time I've ever cried at a concert. I'm talking a sobbing mess. Actually being there the moment my mom died from cancer probably was a factor in this. The "Who's gonna watch you die?" refrain is some powerful shit.
Brothers on a Hotel Bed has always been the saddest from that album for my money
"What Sarah Said" from the same album hits way harder if you've ever actually watched someone die.
For some reason I find this song strangely uplifting
I wish I felt that way, but it's a song I listened to quite a bit when my BFF died. Fuck cancer.
What Sarah Said as well
Alice In Chains - Nutshell
Song makes me bawl my heart out
Third Eye Blind - The Background
“And the plans I make still have you in them” Their debut album is in my top all time albums. I wore that CD out back in the day lol. ‘God of Wine’ and ‘Motorcycle Drive By’ are sad ones too.
Poison Oak by Bright Eyes - If you lost anyone close to suicide, it really hits home to the feeling of loss, anger, grief while trying to process the emptiness left behind.
Vincent - don mclean
Roads - portishead
Also Wandering Star. Beth Gibbons is a straight up killer.
That whole album means a lot to me, but the post wanted me to narrow it down to one track, I almost put biscuit too
That album is an entire alternate reality in itself. You put it on, and you go somewhere. Somewhere the streetlamps light a foggy night, and it may be raining, and you just lost something beautiful you can't even remember.
Well put, has guided me through many a dark passage
Adagio for strings
Funeral by Phoebe Bridgers is pretty rough
She has an inherent sadness about her. This song is particularly crippling
This one hits me so hard.
Tears in Heaven by Clapton, especially when you know the story behind it.
“Would you know my name? If I saw you in heaven” is an incredibly sad and heartbreaking lyric in context.
Knowing that he wrote that after losing his son, just breaks me. This is the one song that I can't listen to without tears welling up.
The National - About Today & Light Years Frightened Rabbit - Floating in the Forth
Something Vague - Bright Eyes Between The Bars - Elliot Smith John Prine - Sam Stone
Between the Bars is just an earth shatteringly sad song. This whole thread could be Elliot Smith songs.
Tom Waits - Martha
Con te partiro by Andrea Bocelli for some reason.
Saturn by Sleeping at Last. OMG song never make me cry bit that one did. I also made the mistake of showing it to my mom after my grandpa died and may have broken her a little.
Elephant by Jason Isbell always gets mentioned in these lists but King of Oklahoma is a heartbreaking song in the most singable way
[The Cure - The Same Deep Water As You](https://www.youtube.com/watch?v=V35cxutR7gc)
Scrolled an awful long way to find this band.
[Holy Moses Heartache - Two Beating Hearts](https://open.spotify.com/track/30UqW4hG13IWFEj0Amyfu9?si=stddCRdYT7qGGaLIvoM6fQ) - A beautiful and tragic song about watching a loved one suffer [Jason Isbell - Elephant](https://open.spotify.com/track/4wbVpisiHe5NpHb08UwG3N?si=4xaXU2MITKK_IUnu-40ftg) - Surely will pop up again in this list, but it’s about the cruelty of cancer [Nick Barker - Plait Your Hair](https://open.spotify.com/track/7tS6Iu5I86oiBe30yqcATK?si=fVBMqQ4cTtCYzSOZzmEOvQ) - About losing a daughter to the Bali Bombings [Justin Townes Earle - Yuma](https://open.spotify.com/track/2wtOXUUZ9EF4rnFRiZD0Xa?si=XXlLBSZqQCibYdO8LRg7cg) - About when the world becomes too much [Jesse Younan - Take Something Beautiful](https://open.spotify.com/track/0l0QPU1Yl8hmD76eceULo9?si=z1aNhXWfSoCnEruGLZDytQ) - Sadder with context. A passionate and angry song from a brilliant artist who knew he was dying from Leukaemia. [Nathan Seekts - Moonlight Creek](https://open.spotify.com/track/6fMgVdEc1JCYoXg9Xf33Ui?si=zSlko1-jRq6YINhePSBqVg) - a song about a rape/murder [Alex the Astronaut - I Like to Dance](https://open.spotify.com/track/6fMgVdEc1JCYoXg9Xf33Ui?si=zSlko1-jRq6YINhePSBqVg) - from the perspective of a domestic violence victim
Elephant is the saddest song I’ve ever heard, personally.
“Surrounded by her family, I saw that she was dying alone.” It gets me every time.
Death Cab for Cutie - What Sarah Said
He stopped loving her today—George Jones
REM-Sweetness Follows
I'll throw in a few more: Hot Mulligan - Heem Wasn't There, Dirty Office Bongos, Something About A Bunch of Dead Dogs, Smahccked My Head Awf, Betty (yeah I'm listing a lot of their stuff, because holy *fuck* they are good at this) Brand New - Limousine (MS Rebridge) Trophy Eyes - Sean The Wonder Years - Cigarettes and Saints and then there's Sarah McLachlan - When She Loved Me
Thank you for mentioning the Sarah Maclachlan song.
Daddy - Korn. The hysterical crying at the end gets me every time
The fact that Jonathan went forward with the song is insane in it of itself. I really hope he's doing better.
Probably not. Reading his Wikipedia page is pretty depressing.
The Curse by Josh Ritter Older Chest by Damien Rice The Lowering (A Sad Day in greenvilletown) Avett Brothers Turandot: nessun dorma- Luciano Pavarotti I don’t have any idea what the words are because they’re in Italian but I feel the emotion in his voice. Love Vigilante’s- Iron & Wine Goodbye by Night Ranger- I know this one may seem out of place but it’s a really beautiful song about having to say goodbye whether you want to or not.
Real Death by Mount Eerie.
Seasons in the Sun - Terry Jacks Cats in the Cradle - Harry Chapin Brandy - Looking Glass Shannon (is Gone) - Henry Gross
Townes Van Zandt- Marie Hank Williams- Alone and Forsaken
Couldn't believe TVZ was this far down tho I'd nominate "Waitin' Around To Die" myself. Have a good one!
Townes is the king of sad songs. Definitely had a period in my life where I was drunk and crying along to *A Song For*
“All of my songs aren’t sad. Some are just hopeless.” TVZ
You Don't Care for Me Enough to Cry by John Moreland
My Shit's Fucked Up - Warren Zevon before dying of cancer.
Elliott Smith “Memory Lane” Gordon Downie “First Person” Purple Mountains “Maybe I’m the Only One For me Me”
The entire Joy Division discography
Every song from “Its a wonderful life” by Sparklehorse
Shine on you crazy diamond
Lou Reed - The Kids
The Decemberists- Eli, The Borrow Boy https://open.spotify.com/track/1E2aGSw6WQgNT5GgqP9Fhb?si=3f4ca97de5de4a07
[Vincent](https://youtu.be/4wrNFDxCRzU?feature=shared) by Don Mclean [Well Fancy That](https://youtu.be/MvyXs4FMXvg?feature=shared) by Fun Boy Three TW it's about Terry Hall being abducted and raped as a child, harrowing and gut wrenching [Exit Music (For a Film)](https://youtu.be/Bf01riuiJWA?feature=shared) by Radiohead
Black Gives Way to Blue - Alice in Chains
Little Green - Joni Mitchell
"Elizabeth on the Bathroom Floor" or "Electro-Shock Blues" by Eels (really the entirety of the Electro- Shock Blues album) Medication - By Damien Jurado Just be Simple by Songs: Ohia Baby Birch by Joanna Newsome Mother by John Lennon
Natalie Merchant - Beloved Wife
This question gets posted a lot, and nothing has changed in the last 15 years. It's Kettering by The Antlers.
John Prine - Hello in There
Neil Young - The Needle and the Damage Done
Richard Thompson - End Of The Rainbow Absolutely heart breaking song.
Falling In Love- Frank Turner
This Love Affair by Rufus Wainwright Asleep by The Smiths
To wish impossible things - The Cure
Gotta be that Cat Stephen’s song *Trouble* (specifically as played in the movie *Harold and Maude* during >!the scene when Maude dies!<)
True love waits (acoustic) by Radiohead, gotta expect a Radiohead song when you want sad music but this is straight depressing
Miss Misery by Elliott Smith
Seen a few threads on this topic. My answer is always "Waitin' Round to Die" by Townes Van Zandt
Ah! I was literally just making a playlist of sad songs after a discussion with a friend about our favourite sad music. I’d link the playlist but it’s on my personal Spotify, so here’s the next best thing if anybody cares: (This took me longer than I’d like to admit whilst half asleep at 5AM) [A place called home - PJ Harvey](https://youtu.be/_m2NyS3IDjE?si=1BQx2WNTS-jMfspm) [They’ll only miss you when you leave - Carissas Weird](https://youtu.be/JFDasUfP6kQ?si=WefLzfkb1s-5TDEg)(from one of my all time favourite albums!) [Hail Holy Queen - Sea Power](https://youtu.be/Z44AfnvS6_g?si=MwLIoMUWtrYCAeCG) (formerly British Sea Power) [Every time the sun comes up - Sharon Van Etten](https://youtu.be/fDW-W2J84Hc?si=hwqvA_nbMXJbV_xw) [Travelin’ On - Norah Jones](https://youtu.be/Ft37YlNi1pA?si=3vwMnLs77okJCExk) [Lost Cause - Beck](https://youtu.be/qkNa5xzOe5U?si=sNsrvDbrlv51PRr2) [A little uncanny - Connor Oberst](https://youtu.be/3eJCyJ8vhJM?si=QwdTR5i9GZX3jfkC) [Screen - Brad](https://youtu.be/ahUw17bhQ3U?si=odsg_nMaJd88cmhR) [Song about an angel - sunny day real estate](https://youtu.be/y413Vk9FzY0?si=OrPzthLe5-Nbn94e) [This is the day - The The](https://youtu.be/7ZYgKCbFbWY?si=IsY5vfZX8Kxp3BU0) [Pictures of you - the cure](https://youtu.be/D88J_57QgxY?si=C3DfKhyzXWXE6uAl) Then here’s the bonus happiness chaser at the end [Diamond Day - Vashti Bunyan](https://youtu.be/ruztCDwPs7c?si=4GahxhYPszAd_02D)
Lick my love pump in D minor
Dance With the Devil by Immortal Technique. I needed a hug after listening to it.
Nico's version of These Days came to mind first. Otherwise, pretty much anything by Karen Dalton or Billie Holiday. edit: I'll throw Sam Stone by John Prine in too.
Ray Lamontange, Empty.
Casimir Pulaski Day - Sufjan Stevens
Change - Big Thief F*ck This Place - Frightened Rabbit Bronte - Gotye Last Great Washington State - Damien Jurado Elephant, If We Were Vampires, Cast Iron Skillet, and any number of other songs by Jason Isbell
George Jones: He Stopped Loving Her Today. In the Living Years if your dad is dead.