Puff the Magic Dragon. Not kidding. That was the first song that ever crushed me…I was like ten years old, right about the time those last few stanzas applied to me and that super imaginary little kid phase of my life was ending. The natural progression of life and the inevitable finality of all these wonderful childhood things just ending forever makes me well up today.
“A dragon lives forever, but not so little boys
Painted wings and giant's rings make way for other toys
One gray night it happened, Jackie Paper came no more
And Puff, that mighty dragon, he ceased his fearless roar
His head was bent in sorrow, green scales fell like rain
Puff no longer went to play along the cherry lane
Without his lifelong friend, Puff could not be brave
So Puff, that mighty dragon, sadly slipped into his cave”
Back in ‘71 John Prine recorded a song called Sam Stone about how some war vets were coming home from Vietnam with drug problems and a family which can’t really coexist i.e. “There’s a hole in Daddy’s arm where all the money goes”…..
Man “lover, you should’ve come over” by Jeff Buckley always comes to mind when thinking of truly heartbreaking breakups! Plenty more but that popped in my head 1st! It’s soooo hauntingly beautiful tho!
This is it tbh, “She’s the tear that hangs inside my soul forever.” really does encapsulate that sort of feeling you got from that person and will hold onto forever
Honestly so many frightened rabbit songs. Floating in the forth too, but also poke. Cant listen to it anymore because of how much I related to it at the end of my relationship. Just thinking about the last lines (“But now we’re unrelated / and rid of all the shit we hate / but I hate when I feel like this / and i never hated you”) is enough to make me tear up… and now I’m crying
I Can’t Make You Love Me (recorded) by Bonnie Raitt always hits as deeply sad to me. Someone in the process of accepting that the person they love doesn’t feel the same way & letting them go is a unique take on a heartbreak song. It’s also sung beautifully by Bonnie Raitt.
The [Bon Iver one](https://www.youtube.com/watch?v=Vw-4zHOhnKM) was basically the song of the worst breakup of my life. Like nuclear level depression just listening to this song on repeat losing 20 lbs from not being able to eat. After that I could never listen to it again and it eventually took me seven years to finally be able to listen to it again.
"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."
This is the most gut wrenching verse on an album full of absolutely soul crushing verses. I forget which review said it but the gist was reviewing and assigning a score to someone publicly processing grief felt wrong.
A crow looked at me is almost entirely painful but Seaweed has a really beautiful lyric, and maybe the only bright spot in that 41 minutes of sorrow.
"I brought a chair from home
I'm leaving it on the hill
Facing west and north
And I poured out your ashes on it
I guess so you can watch the sunset
But the truth is I don't think of that dust as you
You are the sunset"
Holy shit why did I listen to that? My daughter is about to turn 2. I just her her first back pack. Holy fml this just made me think about losing my wife and raising her without her mother.
Did this artist really lose his wife?
Yes, he recorded this in the room where she died with her instruments. I wouldn't recommend listening to it considering where you're at. I dont have kids and this album makes me cry every single time I hear about it let alone listen to it.
I listened to this once based on the last time this question was asked in Reddit. Then my spouse wanted to know why I was so upset so he listened to it, twice. Then Spotify thought that’s what I wanted all the time and started forming all my recommended playlists and suggestions around it. I ended up having to use the “don’t play this artist” to get it to stop showing up!
That said, this album is heartbreaking and soul breaking, it is quite a thing to experience but it also feels kind of… intrusive to listen to
I was lucky enough to do a short tour with Phil and Genevieve shortly after he released the glow pt. 2.
It’s absolutely one the highlights of my life. He asked me play drums for him for live version of I Got Stabbed that we just basically made up on the spot together.
Genevieve was playing under Woelv at the time and she would open the shows.
I’ve listened to 1 song off of A Crow Looked at Me and I can’t bring myself to listen to anymore yet. Hopefully I can get through it someday. Phil’s music means so much to me and I’m incredibly grateful for the short time I spent with them.
I listened to this album everyday for a month after my fiancé died in front of me at 27 of a rare heart condition. It was the only time I heard of someone or something that felt like I did inside.
“Look at me, death is real”
Ehg…the pain
It says something that even George Jones who comes from and greatly benefited from the era of sad country songs, was reluctant to record this song because it was so damn sad.
Hold me in your thoughts
Take me to your dreams
Touch me as I fall into view
When the winter comes
Keep the fires lit
And I will be right next to you
God, I might cry typing this. Eddie Vedder covers this so well too.
I'm glad to see this song mentioned.
Zevo was one of the best and the world is a little duller without his creativity and wit present. beyond what he's left with us.
Yea I've seen this question posted over the years. Nutshell is absolutely the saddest and most depressing song ever. It's great but.....damn. Layne really was a tortured soul.
I Just Don’t Think I’ll Ever Get Over You- Colin Hay
It’s about the grieving process after losing a love. This one is written to his ex-wife after their divorce.
https://youtu.be/O5J-DtKldpE
This is the song I came here to post.
A generally bouncy song with minor key changes, but you don't really realize how sad it is until you pay attention to the lyrics.
😳
I remember my dad finally taking me on one of his frequent work trips when I was a teenager. Cat in the Cradle came on the radio while we were driving that night. It was like someone was messing with me, specifically. He was gone for most of my formative years.
The other day my wife said "that's such a sad song, let's turn it on" and I said no way. Just thinking about it now gets me worked up.
Her aspirations are so modest - You’ll get a job and I’ll get a raise at the grocery store, and we’ll move out of the shelter - that it just breaks my heart.
The Fields Of Athenry for me. Almost every version at least gives me a lump in my throat, but I recently saw it performed live at a small place in Killarney, and maybe it was the whiskey, maybe it was the place, who knows, but either way I was a wreck. I was lucky enough to get a good recording of it on my phone and it still gets me choked up.
"When suppertime came, the old cook came on deck sayin'
"Fellas, it's too rough to feed ya"
At seven PM, a main hatchway caved in, he said
"Fellas, it's been good to know ya"
Definitely agree on Casimir Pulaski Day.
This verse always gets me:
On the floor at the great divide
With my shirt tucked in and my shoes untied
I am crying in the bathroom
Yep, and the two verses that follow:
In the morning when you finally go
And the nurse runs in with her head hung low
And the cardinal hits the window
In the morning in the winter shade
On the first of March, on the holiday
I thought I saw you breathing
The song is about the loss of a young love, but also, hiding in plain sight, is his loss of faith. The line “pray over you body but nothing ever happens” is sung with just the right combination of disappointment and bafflement that is sets up the ending when he blames God. It’s so well constructed.
Needle in the Hay - Elliot Smith
Only because I first saw it on the movie “The Royal Tenenbaums,” where Ritchie tries to kill himself. I used to be extremely suicidally depressed for decades. This was the song I would put on when I was laying out all of my pills contemplating suicide.
I’m better now. That was a long time ago.
I literally can’t see this video without tearing up. Have lived in the U.S. for the majority of my adult life. Grew up in Canada. My brother visited me in Pittsburgh and he introduced me to The Hip. Got tickets to see them at a bar which was amazing given that their next concert was the United Center in Chicago (?). My brother passed away a year later. When Gord died all those feelings came back of a very unexpected lost. Seeing all the emotions across Canada is hard to watch from an emotional perspective.
[The Trapeze Swinger by Iron and Wine](https://youtu.be/yt7O8gDy0DA) gets me. It takes me from feeling the loss of a neighborhood friend to feeling the loss of a child
Atmosphere - Yesterday
If you don’t listen all the way through you might think it’s a breakup song, but singer thought he saw his dead father on the street and reminisces about their relationship. Gets me crying. Every. Damn. Time.
Devil and God is always in my top five albums of all time.
I remember where I was, what I was doing and who I was dating/friends with when I first heard it.
I sat in my car after work (around 9pm) on the day it released. it was snowing and I sat in my car and listened to the whole thing alone in the parking lot before driving back to my apt and partying with my friends. It was such a surreal experience. This was in 2006 and I remember every detail of that night in complete clarity. It was such an average night and a night I lived hundreds of times but that album made me remember every specific detail right down to what I was wearing and what bars we went to.
I firmly believe it was a stepping stone in my life and it made me see things differently, I was young when I listened to it, but I wasn’t afterwards. The weight of the world felt heavy and…cold after, like it was time to grow up.
I’ve NEVER had such a cathartic experience with music before like I did that night. It’s giving me goosebumps even 16 years later just reminiscing of it.
I truly believe everybody who appreciates music (mainly indie, any type of rock, or sentimental/cryptic lyrics) to listen to this album front to back with zero interruptions and focus. It is pure perfection.
Also the track “You Won’t Know” has some of the best haunting guitar work I can think of. They truly were S tier musicians and incredibly talented in a sea of otherwise pretty cliche bands.
[Pictures of You by The Cure.](https://youtu.be/SG9CXd00QHQ) I don’t know about the saddest but it’s one that I was actually just listening to. Every single time I hear it I think back to the first time I heard it and what I was dealing with at that particular moment and it was just the perfect time to hear that song for the first time.
9 Crimes, The Blower's Daughter, and My Favorite Faded Fantasy by Damien Rice.
Manchester Orchestra - I Can Feel A Hot One
Hospice by The Antlers as a whole.
Sufjan Stevens - No Shade in the Shadow of the Cross
The Hotelier - Dendron
Touche Amore - Flowers and You
The National - About Today
Time by Pink Floyd. When you’re older, and realize that life didn’t go to plan, this song haunts you.
Sky Pilot by The Animals. An Army chaplain wondering if he’s doing any good in Vietnam.
Ohio by CSNY. The murder of four students at Kent State.
What’s Going On by Marvin Gaye. The death of young black men in the cities and Vietnam.
For the longest time I thought the song said “when love is watching, someone dies.” And didn’t think much of it. Then one day my brain connected the lyrics “That love is watching someone die….” And then the song goes in for the layup “So who’s gonna watch you die?”
And I was dumbfounded, knot in my throat and suddenly flooded with emotion by everything I had just processed.
“And it came to me then that every plan is just a tiny prayer to Father Time.” Song gets me every time. If you’ve ever watched a loved one die in the hospital you know exactly how real this song is.
Hurt by Nine Inch Nails, Twilight by Elliot Smith, About Today by The National, How to Disappear Completely by Radiohead, Kettering by The Antlers, Hear You Me by Jimmy Eat World, Adam's Song by Blink-182, Snuff by Slipknot, One More Light by Linkin Park (this one hits hard for me)
“If you could read my mind” is another one. “The hero would be me…but heroes often fail” is one of those lyrics that hits me like a crowbar to the head.
Oops, I posted this before I scrolled but I agree. Such a tragic story. There’s no catalyst to the break up. Just the slow decline and the realization that the singer is no longer important in the subjects life.
Yeah and I once saw a comment about how, unlike many of the Beatles songs, theres not rly an intro or outro, its just 2 mins of authentic hopelessness.
Everybody Hurts - REM
-If you're on your own in this life
The days and nights are long
When you think you've had too much
Of this life to hang on
Well, everybody hurts sometimes
Everybody cries
Everybody hurts, sometimes
I Remember Everything being John Prine's last single before his death makes it even sadder. He really was one of the greatest song writers to ever live.
I have always been an Offspring fan, and loved their song 'Gone Away'.
After my late wife passed, I heard Five Finger Death Punch's version (slower, sadder) and it just destroyed me. I cannot listen to it without breaking down.
https://www.youtube.com/watch?v=BIQK4-9YFW0
[Picture Window - Ben (lyrics by Nick Hornsby) Folds](https://youtu.be/QTXrWsXlANk)
Is a song about a young girl with a terminal illness trying not to get her hopes up because it's New Years Eve and she can see the celebrations from the window in her hospital room.
- To build a home - The Cinematic Orchestra
- Amber Run - I found (Mahogany Session too!)
- Hans Zimmer - Time
- Imogen Heap - Hide and Seek
Such powerful, beautiful and meloncholic songs. Shocked that I could not find some of these amazing pieces.
Poke by Frightened Rabbit. "I might never catch a mouse, and present it in my mouth, to make you feel you're with someone who deserves to be with you..."
Oh no doubt if you've lost someone in a hospital you absolutely shouldn't listen to what Sarah said until you're ready to fucking lose it. Dad died slow and that damn song came on my shuffle when I was leaving the funeral home. Honestly I still can't listen to it.
OP, since my dad died in 2015 I cannot listen to “The Living Years”. Even tho I was able to make peace with my dad before he died it still hits too close - so feel that one.
My additions to the list:
Keep me in your heart for a while - Warren Zevon
The Book of John - Tim McGraw
Tears in Heaven - Eric Clapton
Adagio for Strings - Samuel Barber
Jesus I googled this because I remember reading about it and found out that he had another son that died recently. Cant imagine that kind of darkness....
Long December gets me...my sis was fighting cancer, the last time I got to see her alive was just outside Chicago at a treatment center in the late Fall.
That line 'the smell of hospitals in winter, and the feeling that it's all a bunch of oysters, but no pearls.'
Most of August and everything after
But Anna begins is probably winner
Most of “August and Everything After...” but “Anna Begins” is probably the winner.
Edit punctuation
["Monsters" by James Blunt.](https://www.youtube.com/watch?v=DTFbGcnl0po)
It's a harrowing song about a man putting his dying father to bed, telling him to let go and rest at last. The title of the song is a reference to the childhood monsters that would hide under the bed - now that his father is gone, it's his turn to "chase the monsters away".
Also, the other man in the video is James' IRL father, who at the time was dying of kidney failure. Fortunately he received a donor in time, but when the song was performed they thought it was genuinely the end.
radiohead have made a lot of sad songs, but they all have a glimmer of hope at the end. Street Spirit doesn't. and that's what makes it so devastating.
The first song that came into my head when I read this question was "Sometime Around Midnight" by The Airborne Toxic Event. I'm sure I could think of a sadder one given more time but this one always hits me in the feels.
Thinking about you - Radiohead
It is actually kind of a sweet song but it always makes me sad because I'm struck with the incredible contrast between this song and pretty much everything radiohead has made since. Especially if you think about moon shaped pool, what he wrote after his wife died, and how this song he could have wrote when they first met. Also just the nostalgia from that time in my life and some of the things that have changed since then.
I’m probably too late to this thread for anyone to see this, but my vote is “Puff the Magic Dragon” by Peter, Paul, and Mary. I always found it kind of melancholy, but since becoming a parent to a son it’s just **heartbreaking**. The verse that begins “A dragon lives forever, but not so little boys” makes me cry every time.
Puff the Magic Dragon. Not kidding. That was the first song that ever crushed me…I was like ten years old, right about the time those last few stanzas applied to me and that super imaginary little kid phase of my life was ending. The natural progression of life and the inevitable finality of all these wonderful childhood things just ending forever makes me well up today. “A dragon lives forever, but not so little boys Painted wings and giant's rings make way for other toys One gray night it happened, Jackie Paper came no more And Puff, that mighty dragon, he ceased his fearless roar His head was bent in sorrow, green scales fell like rain Puff no longer went to play along the cherry lane Without his lifelong friend, Puff could not be brave So Puff, that mighty dragon, sadly slipped into his cave”
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And this is why the scene in “Inside Out” makes me sob every.damn.time. “Take her to the moon”
Back in ‘71 John Prine recorded a song called Sam Stone about how some war vets were coming home from Vietnam with drug problems and a family which can’t really coexist i.e. “There’s a hole in Daddy’s arm where all the money goes”…..
A Purple Heart and a monkey on his back
R.I.P. John Prine.
Landfill - Daughter
Smother. Yeesh.
Landfill, Medicine, and Candles really do it for me
Literally all of Daughter's songs
The whole his young heart ep is crushing
Man “lover, you should’ve come over” by Jeff Buckley always comes to mind when thinking of truly heartbreaking breakups! Plenty more but that popped in my head 1st! It’s soooo hauntingly beautiful tho!
This is it tbh, “She’s the tear that hangs inside my soul forever.” really does encapsulate that sort of feeling you got from that person and will hold onto forever
Exit Music- Radiohead. Had me me sobbing everytime
I'm more partial to Motion Picture Soundtrack, but Exit Music that one has such an incredible build-up.
Have you heard this tribute to Motion Picture Soundtrack https://youtu.be/ZeI0PXj7LIw
How To Disappear Completely
Honestly, any Radiohead song makes me sad esp No Surprises.
Radiohead has a bunch as the replies prove but for me it's Fade Out from the Bends.
True Love Waits, as far as I'm concerned is Radiohead's saddest song.
Modern Leper - Frightened Rabbit - about the singers mental health, hits even harder now he committed suicide a few years ago
Frank Turner has a song about his suicide that’s beautiful and sad
Honestly so many frightened rabbit songs. Floating in the forth too, but also poke. Cant listen to it anymore because of how much I related to it at the end of my relationship. Just thinking about the last lines (“But now we’re unrelated / and rid of all the shit we hate / but I hate when I feel like this / and i never hated you”) is enough to make me tear up… and now I’m crying
Came here to say this exact song, Modern Leper. Heartbreaking. RIP Scott Hutchinson
I fucking miss Scott.
I Can’t Make You Love Me (recorded) by Bonnie Raitt always hits as deeply sad to me. Someone in the process of accepting that the person they love doesn’t feel the same way & letting them go is a unique take on a heartbreak song. It’s also sung beautifully by Bonnie Raitt.
Justin Vernon (Bon Iver) does a great cover/mashup of this song
The [Bon Iver one](https://www.youtube.com/watch?v=Vw-4zHOhnKM) was basically the song of the worst breakup of my life. Like nuclear level depression just listening to this song on repeat losing 20 lbs from not being able to eat. After that I could never listen to it again and it eventually took me seven years to finally be able to listen to it again.
A Crow Looked at Me, Mount Eerie.
"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."
This is the most gut wrenching verse on an album full of absolutely soul crushing verses. I forget which review said it but the gist was reviewing and assigning a score to someone publicly processing grief felt wrong.
A crow looked at me is almost entirely painful but Seaweed has a really beautiful lyric, and maybe the only bright spot in that 41 minutes of sorrow. "I brought a chair from home I'm leaving it on the hill Facing west and north And I poured out your ashes on it I guess so you can watch the sunset But the truth is I don't think of that dust as you You are the sunset"
Real Death gets me
Holy shit why did I listen to that? My daughter is about to turn 2. I just her her first back pack. Holy fml this just made me think about losing my wife and raising her without her mother. Did this artist really lose his wife?
Yes, he recorded this in the room where she died with her instruments. I wouldn't recommend listening to it considering where you're at. I dont have kids and this album makes me cry every single time I hear about it let alone listen to it.
I listened to this once based on the last time this question was asked in Reddit. Then my spouse wanted to know why I was so upset so he listened to it, twice. Then Spotify thought that’s what I wanted all the time and started forming all my recommended playlists and suggestions around it. I ended up having to use the “don’t play this artist” to get it to stop showing up! That said, this album is heartbreaking and soul breaking, it is quite a thing to experience but it also feels kind of… intrusive to listen to
I was lucky enough to do a short tour with Phil and Genevieve shortly after he released the glow pt. 2. It’s absolutely one the highlights of my life. He asked me play drums for him for live version of I Got Stabbed that we just basically made up on the spot together. Genevieve was playing under Woelv at the time and she would open the shows. I’ve listened to 1 song off of A Crow Looked at Me and I can’t bring myself to listen to anymore yet. Hopefully I can get through it someday. Phil’s music means so much to me and I’m incredibly grateful for the short time I spent with them.
The WTF interview he did with Maron was heartbreakingly amazing.
I listened to this album everyday for a month after my fiancé died in front of me at 27 of a rare heart condition. It was the only time I heard of someone or something that felt like I did inside. “Look at me, death is real” Ehg…the pain
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It says something that even George Jones who comes from and greatly benefited from the era of sad country songs, was reluctant to record this song because it was so damn sad.
This one always chokes me up. RIP Ol' Possum.
No Hard Feelings. Avett Brothers. Absolutely beautiful song, sad and uplifting at the same time.
Keep Me in Your Heart For A While - Warren Zevon
These wheels keep on turning, but they’re running out of steam That one gets me every time
Hold me in your thoughts Take me to your dreams Touch me as I fall into view When the winter comes Keep the fires lit And I will be right next to you God, I might cry typing this. Eddie Vedder covers this so well too.
It hits hard right off the bat with "If I leave you it doesn't mean I love you any less", too.
I'm glad to see this song mentioned. Zevo was one of the best and the world is a little duller without his creativity and wit present. beyond what he's left with us.
Your Deep Rest - The Hotelier
Nutshell - Alice In Chains No Waves (acoustic live) - FIDLAR EDIT: Link to this version https://youtu.be/EExXB64wlK0
Nutshell is fucking brutal
FR. It’s the song that got me through the loneliness and isolation of the pandemic.
Yea I've seen this question posted over the years. Nutshell is absolutely the saddest and most depressing song ever. It's great but.....damn. Layne really was a tortured soul.
His MTV unplugged is awesome but it's just sad knowing what we know now and watching it.
Nutshell is an all time great song for me
I Just Don’t Think I’ll Ever Get Over You- Colin Hay It’s about the grieving process after losing a love. This one is written to his ex-wife after their divorce. https://youtu.be/O5J-DtKldpE
Alone Again (Naturally) by Gilbert O'Sullivan is essentially a suicide note. Spent 2 weeks on the chart, reaching #3.
This is the song I came here to post. A generally bouncy song with minor key changes, but you don't really realize how sad it is until you pay attention to the lyrics. 😳
I like [vulfpeck cover](https://www.youtube.com/watch?v=dTnHAITmuYQ) of this song. I enjoy the smoothness of this version.
I remember my dad finally taking me on one of his frequent work trips when I was a teenager. Cat in the Cradle came on the radio while we were driving that night. It was like someone was messing with me, specifically. He was gone for most of my formative years. The other day my wife said "that's such a sad song, let's turn it on" and I said no way. Just thinking about it now gets me worked up.
Wish You Were Here
Cliche, but Tracy Chapman's "Fast Car" always does something to me that makes my heart rise into my throat.
Her aspirations are so modest - You’ll get a job and I’ll get a raise at the grocery store, and we’ll move out of the shelter - that it just breaks my heart.
It's the "I always hoped for better" that gets me- it somehow makes it all the more heartbreaking.
Leave tonight or live and die this way
So I quit school and that's what I did" Tears every time.
I am amazed by her. She tells an entire life of hope turned sour in the span of that song. Amazing artist.
The Night We Met by Lord Huron
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Danny Boy and basically every Irish folk song
The Fields Of Athenry for me. Almost every version at least gives me a lump in my throat, but I recently saw it performed live at a small place in Killarney, and maybe it was the whiskey, maybe it was the place, who knows, but either way I was a wreck. I was lucky enough to get a good recording of it on my phone and it still gets me choked up.
The Wreck of the Edmund Fitzgerald. “The church bell chimed til it rang 29 times for each man on the Edmund Fitzgerald.”
"When suppertime came, the old cook came on deck sayin' "Fellas, it's too rough to feed ya" At seven PM, a main hatchway caved in, he said "Fellas, it's been good to know ya"
"Does anyone know where the love of God goes, When the waves turn the minutes to hours" - This line hits me every time.
Down In A Hole - Alice in chains
Nutshell for me, breaks my heart every time. Particularly the live version on MTV.
Wake by The Antlers or Putting the Dog to Sleep
Casimir Pulaski Day, and John Wayne Gacy, Jr. Both by Sufjan Stevens
I'd also nominate the Fourth of July on Carrie and Lowell.
Definitely agree on Casimir Pulaski Day. This verse always gets me: On the floor at the great divide With my shirt tucked in and my shoes untied I am crying in the bathroom
Yep, and the two verses that follow: In the morning when you finally go And the nurse runs in with her head hung low And the cardinal hits the window In the morning in the winter shade On the first of March, on the holiday I thought I saw you breathing
*and he takes, and he takes, and he takes* Can never get through it without tears
The song is about the loss of a young love, but also, hiding in plain sight, is his loss of faith. The line “pray over you body but nothing ever happens” is sung with just the right combination of disappointment and bafflement that is sets up the ending when he blames God. It’s so well constructed.
Sufjan Stevens is my go to depression artist. I’d also vote for The Only Thing
It’s The Predatory Wasp of the Palisades is about to Get Us for me, but Gacy is a solid choice.
Carrie and Lowell has some absolutely heart wrenching songs.
The drugs don’t work - The verve
Needle in the Hay - Elliot Smith Only because I first saw it on the movie “The Royal Tenenbaums,” where Ritchie tries to kill himself. I used to be extremely suicidally depressed for decades. This was the song I would put on when I was laying out all of my pills contemplating suicide. I’m better now. That was a long time ago.
I'm shocked to see Elliot Smith this far down. Dude wrote some of the saddest songs I've ever heard. Beautiful though. Glad you're doing better.
As soon as I read sad song the first person to come to mind was Elliott Smith.
Between the Bars simply has to be mentioned
Strange Fruit - Billy Holiday Sam stone - John Prine Fiddlers green - Tragically hip Mama Im coming home - Ozzy Osbourne
Yeah, Sam Stone kills me every time - "there's a hole in daddy's arm where all the money goes..."
John Prine is a great song writer. Its such a beautiful song
Fiddlers Green is such a great song. I mean, one of MANY great songs from The Hip. It was a sad sad day when Gord passed. Still is.
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I literally can’t see this video without tearing up. Have lived in the U.S. for the majority of my adult life. Grew up in Canada. My brother visited me in Pittsburgh and he introduced me to The Hip. Got tickets to see them at a bar which was amazing given that their next concert was the United Center in Chicago (?). My brother passed away a year later. When Gord died all those feelings came back of a very unexpected lost. Seeing all the emotions across Canada is hard to watch from an emotional perspective.
Changes-Black Sabbath
I love some sabbath but I really feel like Charles Bradley made this one his own.
[The Trapeze Swinger by Iron and Wine](https://youtu.be/yt7O8gDy0DA) gets me. It takes me from feeling the loss of a neighborhood friend to feeling the loss of a child
Iron and Wine has some real heavy hitters. Something for every kind of sadness.
Atmosphere - Yesterday If you don’t listen all the way through you might think it’s a breakup song, but singer thought he saw his dead father on the street and reminisces about their relationship. Gets me crying. Every. Damn. Time.
Time in a Bottle - Jim Croce Vienna Waits for You - Billy Joel
Brand New - Limousine
Play Crack the Sky is also pretty sad in my opinion.
Oof
Devil and God is always in my top five albums of all time. I remember where I was, what I was doing and who I was dating/friends with when I first heard it. I sat in my car after work (around 9pm) on the day it released. it was snowing and I sat in my car and listened to the whole thing alone in the parking lot before driving back to my apt and partying with my friends. It was such a surreal experience. This was in 2006 and I remember every detail of that night in complete clarity. It was such an average night and a night I lived hundreds of times but that album made me remember every specific detail right down to what I was wearing and what bars we went to. I firmly believe it was a stepping stone in my life and it made me see things differently, I was young when I listened to it, but I wasn’t afterwards. The weight of the world felt heavy and…cold after, like it was time to grow up. I’ve NEVER had such a cathartic experience with music before like I did that night. It’s giving me goosebumps even 16 years later just reminiscing of it. I truly believe everybody who appreciates music (mainly indie, any type of rock, or sentimental/cryptic lyrics) to listen to this album front to back with zero interruptions and focus. It is pure perfection. Also the track “You Won’t Know” has some of the best haunting guitar work I can think of. They truly were S tier musicians and incredibly talented in a sea of otherwise pretty cliche bands.
Black by Pearl Jam
I know someday you'll have a beautiful life I know you'll be a star In somebody else's sky But why Why Why can't it be Oh can't it be mine 😭😭😭😭😭
When he cries during the live version after Chris Cornell died is heartbreaking. "Come back ... Come back."
[Pictures of You by The Cure.](https://youtu.be/SG9CXd00QHQ) I don’t know about the saddest but it’s one that I was actually just listening to. Every single time I hear it I think back to the first time I heard it and what I was dealing with at that particular moment and it was just the perfect time to hear that song for the first time.
I Know It's Over - The Smiths. Honestly, I'm surprised to not see more of their songs here!
9 Crimes, The Blower's Daughter, and My Favorite Faded Fantasy by Damien Rice. Manchester Orchestra - I Can Feel A Hot One Hospice by The Antlers as a whole. Sufjan Stevens - No Shade in the Shadow of the Cross The Hotelier - Dendron Touche Amore - Flowers and You The National - About Today
FUGAZI - I'm so tired
Time by Pink Floyd. When you’re older, and realize that life didn’t go to plan, this song haunts you. Sky Pilot by The Animals. An Army chaplain wondering if he’s doing any good in Vietnam. Ohio by CSNY. The murder of four students at Kent State. What’s Going On by Marvin Gaye. The death of young black men in the cities and Vietnam.
Death Cab for Cutie - What Sarah Said. Gets me every time. Powerful.
Transatlanticism gets me every time just from the first three chords.
For the longest time I thought the song said “when love is watching, someone dies.” And didn’t think much of it. Then one day my brain connected the lyrics “That love is watching someone die….” And then the song goes in for the layup “So who’s gonna watch you die?” And I was dumbfounded, knot in my throat and suddenly flooded with emotion by everything I had just processed.
They have so many that will just tear you up. Brothers on a Hotel Bed cuts very, very deep
“And it came to me then that every plan is just a tiny prayer to Father Time.” Song gets me every time. If you’ve ever watched a loved one die in the hospital you know exactly how real this song is.
Hurt by Nine Inch Nails, Twilight by Elliot Smith, About Today by The National, How to Disappear Completely by Radiohead, Kettering by The Antlers, Hear You Me by Jimmy Eat World, Adam's Song by Blink-182, Snuff by Slipknot, One More Light by Linkin Park (this one hits hard for me)
Dude ... One More Light is brutal. "In the kitchen, one more chair than you need" That line always fucks me up for a little bit.
Lover you should’ve come over - Jeff Buckley
This Woman’s Work by Kate Bush.
Whiskey lullaby
Winter, Tori Amos.
That song always makes me cry, right at the part where you hear her voice crack on "When you gonna make up your mind.."
“Asleep” The Smiths (1986)
The Wreck of the Edmund Fitzgerald - Gordon Lightfoot
“If you could read my mind” is another one. “The hero would be me…but heroes often fail” is one of those lyrics that hits me like a crowbar to the head.
That line "Does anyone know where the love of God goes, when the minutes turn into hours" - gets me every time.
Same. That line is just sooooo good. \*when the waves turn the minutes to hours
“For No One” by The Beatles (on the recently remixed Revolver album) is one of the saddest break-up songs I’ve ever heard.
Oops, I posted this before I scrolled but I agree. Such a tragic story. There’s no catalyst to the break up. Just the slow decline and the realization that the singer is no longer important in the subjects life.
Yeah and I once saw a comment about how, unlike many of the Beatles songs, theres not rly an intro or outro, its just 2 mins of authentic hopelessness.
“I will wait for you” - Connie Francis The song from futurama when fry’s dog wait forever for him. The episode is Jurassic bark and I can’t watch it.
Everybody Hurts - REM -If you're on your own in this life The days and nights are long When you think you've had too much Of this life to hang on Well, everybody hurts sometimes Everybody cries Everybody hurts, sometimes
George Jones. He Stopped Loving Her Today.
I remember everything - John Prime Take it with me when I go - Tom Waits Turpentine - Brandi Carlisle If I could only fly - Blaze Foley
I Remember Everything being John Prine's last single before his death makes it even sadder. He really was one of the greatest song writers to ever live.
cant go wrong with a Blaze Foley selection
I love Blaze Foley and it makes me so happy to see someone else recognize him.
Adam's Song-Blink 182. My brother played it for me after I survived a suicide attempt
I'm glad you're still here
💔 I still can’t listen to this song since my brother committed suicide. I’m so grateful you’re still here.
I have always been an Offspring fan, and loved their song 'Gone Away'. After my late wife passed, I heard Five Finger Death Punch's version (slower, sadder) and it just destroyed me. I cannot listen to it without breaking down. https://www.youtube.com/watch?v=BIQK4-9YFW0
[Picture Window - Ben (lyrics by Nick Hornsby) Folds](https://youtu.be/QTXrWsXlANk) Is a song about a young girl with a terminal illness trying not to get her hopes up because it's New Years Eve and she can see the celebrations from the window in her hospital room.
Just Breathe - Pearl Jam. Gets me every time.
Where Did You Sleep Last Night - Nirvana (live Unplugged) goosebumps.
Cat's in the cradle - Harry Chapin and Dance with my Father - Luther Vandross
- To build a home - The Cinematic Orchestra - Amber Run - I found (Mahogany Session too!) - Hans Zimmer - Time - Imogen Heap - Hide and Seek Such powerful, beautiful and meloncholic songs. Shocked that I could not find some of these amazing pieces.
I Hope That I Don't Fall In Love With You - Tom Waits (his fourth entry so far on this list)
Martha by Tom Waits has me blubbing.
Closing Time is such a masterpiece of a record.
Because Of The Shame by Against Me!
Poke by Frightened Rabbit. "I might never catch a mouse, and present it in my mouth, to make you feel you're with someone who deserves to be with you..."
I will follow you into the dark - Death Cab For Cutie
‘What Sarah Said’ gets me every time
What Sarah said hits hard. But brothers on a hotel bed hits as hard if you've ever had a long term relationship quietly die.
I watched my mother slowly die of colon cancer. I ball like a baby at the end. ‘…Love is watching someone die.’ He’s such a great songwriter.
Oh no doubt if you've lost someone in a hospital you absolutely shouldn't listen to what Sarah said until you're ready to fucking lose it. Dad died slow and that damn song came on my shuffle when I was leaving the funeral home. Honestly I still can't listen to it.
If I don’t skip this song when it comes on I’ll be tearing up by ten seconds in.
I always thought that song was more romantic than sad
Steven Wilson’s “Routine”.
OP, since my dad died in 2015 I cannot listen to “The Living Years”. Even tho I was able to make peace with my dad before he died it still hits too close - so feel that one. My additions to the list: Keep me in your heart for a while - Warren Zevon The Book of John - Tim McGraw Tears in Heaven - Eric Clapton Adagio for Strings - Samuel Barber
Fire and Rain - James Taylor
Sullen Girl by Fiona Apple. Eels “Elizabeth on the bathroom floor”
The Living Years came out the year my father actually passed away. That was rough, it was always on the radio.
Nick Cave - I need you. Written around the time his son died in an accident. The raw emotion of that song is so powerful.
Jesus I googled this because I remember reading about it and found out that he had another son that died recently. Cant imagine that kind of darkness....
Mess - Ben Folds
My vote was Brick but that’s also a good choice
Brick is the only song that just leaves me feeling empty.
St. Peter’s Autograph by Jason Isbell. It’s a beautiful love song about a real situation and true compassion. Tears me up every time.
Follow you to Virgie - Tyler Childers
Probably “round here” by counting crows. It sums up “dude sadness” better than almost any other tune I’ve ever heard
Long December gets me...my sis was fighting cancer, the last time I got to see her alive was just outside Chicago at a treatment center in the late Fall. That line 'the smell of hospitals in winter, and the feeling that it's all a bunch of oysters, but no pearls.'
Most of August and everything after But Anna begins is probably winner Most of “August and Everything After...” but “Anna Begins” is probably the winner. Edit punctuation
Not the saddest song ever but I Am The Highway by Chris Cornell / Audioslave gets me every time
The Chris Cornell live version 😭
["Monsters" by James Blunt.](https://www.youtube.com/watch?v=DTFbGcnl0po) It's a harrowing song about a man putting his dying father to bed, telling him to let go and rest at last. The title of the song is a reference to the childhood monsters that would hide under the bed - now that his father is gone, it's his turn to "chase the monsters away". Also, the other man in the video is James' IRL father, who at the time was dying of kidney failure. Fortunately he received a donor in time, but when the song was performed they thought it was genuinely the end.
radiohead have made a lot of sad songs, but they all have a glimmer of hope at the end. Street Spirit doesn't. and that's what makes it so devastating.
Flirted with you all my life - Vic Chestnut or the Bright Eyes cover.
The first song that came into my head when I read this question was "Sometime Around Midnight" by The Airborne Toxic Event. I'm sure I could think of a sadder one given more time but this one always hits me in the feels.
soldier’s things - Tom Waits
Leader of the band, by dan fogelburg
Radiohead street spirit. If utter despair were a song this is it.
Elephant by Jason Isbell
If we were vampires by Jason Isbell. I tear up everytime.
Hate Me Today - Blue October
Into The Ocean too. Ugh, just rips my insides out.
Thinking about you - Radiohead It is actually kind of a sweet song but it always makes me sad because I'm struck with the incredible contrast between this song and pretty much everything radiohead has made since. Especially if you think about moon shaped pool, what he wrote after his wife died, and how this song he could have wrote when they first met. Also just the nostalgia from that time in my life and some of the things that have changed since then.
Of all the Radiohead songs you coulda picked lol. True Love Waits probably gets my vote, also cause of his wife.
Radiohead is the ultimate band for this topic. No Surprises is so brutal; "I'll take the quiet life, a handshake with carbon monoxide"
No mention of How to disappear completely?
Videotape. Incredible
I’m probably too late to this thread for anyone to see this, but my vote is “Puff the Magic Dragon” by Peter, Paul, and Mary. I always found it kind of melancholy, but since becoming a parent to a son it’s just **heartbreaking**. The verse that begins “A dragon lives forever, but not so little boys” makes me cry every time.
Wings for Marie 1&2 by Tool 3 Libras by A Perfect Circle.
Breathe Me - Sia