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Saddest, Most Depressing or Gut Wrenching Songs

Castle

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What songs make you cry?

Jim Croce's Operator is a tear jerker for me. Otherwise known as That's Not The Way It Feels, written from the perspective of a guy calling the telephone operator to get him in touch with a long lost love, the song was inspired by Croce's experience serving in Vietnam with soldiers whose girlfriends dumped them while they were serving overseas.

It's the second verse that always gets me:
Operator., oh won't you help me place this call
Cuz I can't read the number that you just gave me
There's something in my eyes
You know it happens every time
I think about the love that I thought would save me


At 12:15 pm on November 9, 1975, the Edmund Fitzgerald set out from Superior, Wisconsin on what was to be her final voyage. After midnight the next day, the Great Lakes were beset by a terrible winter storm. The Fitzgerald and the Arthur M. Anderson would weather the storm together, until 7pm when the Anderson lost all contact with the Fitzgerald. The last reply from Fitzgerald Captain Ernest M. McSorley, "We're holding our own." There were 29 men on board.

The legend was immortalized by folk singer Gordon Lightfoot in his 1976 hit "The Wreck of the Edmund Fitzgerald." The song takes some liberties but gets many of the details right while leaving some of the more poignant details out. A haunting electric guitar riff accompanies the melody, and the song picks up at the moment the storm sets in. While the song goes on for a few more verses than I think is necessary, it is poetically lyrical throughout - and a glorifying tribute to the 29 men lost at sea.

Cats In The Cradle by Harry Chapin

There's a popular game that goes way back. It's simple. See how long it takes until the first person starts crying to Cats In The Cradle. The song tells the oft repeated (and oft experienced) tale of a boy whose working father is never around, too busy supporting the family to spend time with his son. Until the day comes when the boy is grown and the father wants to spend time with him. By now, the new man has his own family and his own obligations and no time to spend with his father. The cruelest of ironies.

Alright... here it is. The greatest song ever written. That's right. It's my all time favorite song. Supertramp's Long Way Home.

I'm sorry I can't find a video for this as for some reason someone does a really thorough job keeping the studio version off of Youtube. (and the few live performances and re-recordings to be found just don't do it justice.) Besides, everyone owes it to themselves to listen to the entirely of Supertramp's Breakfast In America album at least once.

On the surface, the song is about a man whose wife is so uninterested in him that he would rather take a long time coming home than be with her. Underneath, the song is a metaphor for life and the journey we take through it. According to singer songwriter Rodger Hodgson, "I really believe we all want to find our home, find that place in us where we feel at home, and to me, home is in the heart and that is really, when we are in touch with our heart and we're living our life from our heart, then we do feel like we found our home."

Beginning with an ominous violin string that starts out just at the edge of hearing and gradually rises until it is abruptly punctuated by a single hard discordant piano note followed by low rambling keys, the absolutely bad ass harmonica courtesy of wind instrument maestro John Helliwell kicks in and rips a haunting chill straight through the heart of this number. The tune rises almost imperceptibly to a tearing clarinet solo just before the final verse, after which it suddenly winds down with a beat reminiscent of a train pulling into the station only to be finished off by the low, lonely melodic weep of the harmonica.

I never fail to shed at least a single tear at the last verse:

Then you feel like your life's become a catastrophe
Oh! It has to be
For you to grow, boy
And when you look through the years and see what you could've been
Oh! What you might of been
If you'd of had more time

Life is long, but the journey can feel short. Make sure to take the long way home.
 
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Half by PVRIS comes to mind for me. I really really love this song because I kind of see it describing the way I feel about myself, even if the meaning isn't necessarily written to be about gender dysphoria, I find it incredibly applicable. Especially when depression and existential dread is thrown into the mix.

I'm almost embarrassed to mention this song because why it makes me sad is kind of pathetic. But, Gravity Slave by Seraphim. This song would get me crying pretty good back when I first got the Tabula Rasa EP, and it didn't help that I would play the song on loop. It's a song with a very... interesting... and sympathetic perspective on the, uh... Fall™. Yeah. That thing. The entire EP is a concept EP around this story, and every single track is a masterpiece, but this track is the one that would get me really emotional. Don't ask...

God Went North by Nothing More is probably one of my all time favorite songs, but really damn depressing. It was written about the singer's mother, who is dying, and when the songs are written so personally about something or someone that means a lot to those in the band, it really shows.

And that brings me to the mention of Architects' closing track of their 2016 album, All Our Gods Have Abandoned Us. Memento Mori. The story of this album is about as depressing as they come. It was essentially a pre-emptive elegy for one of their bandmates, and in writing it, was their way of coming to terms that he was losing his battle with leukemia. The final track, just completely nailed this, and the amount of raw emotion and power that is just coursing through every aspect of the song just gives me chills. The song peaks for me around 5:08 when the song gets really atmospheric before diving back in with probably one of the most devastating and existential lyrical bridges I've ever encountered. "When the veil lifts, how will I know? Will I see... God?" This is probably one of the most impactful moments in any song, to be honest. The grief in the song's tone played in unison with the acceptance in the song's lyrics is beyond moving.

Meet Me at the Gates by blessthefall is another song about grieving over death that really tugs on my heart strings. It's the fact that these songs pry into the "after" and whether or not you will get a reunion that makes them hit hard. Unlike the previous two, blessthefall's band members are more religious, so they have a slightly different attitude about what comes after death, but the story of Meet Me at the Gates is pretty explanatory. It's a hope and desire that you will meet with your loved one again when your own time comes...

A darker counterpart to Meet Me at the Gates is Come With Me to the Other Side by Orden Ogan. This song is lyrically and thematically similar to Meet Me at the Gates, except it is from the perspective of the person who is being grieved over. The song is less about loss and more about the broken mindset of someone contemplating suicide (hence the backward perspective of the song), which also makes it strike very hard for me, but it is very beautifully done.

--Also because I have no self control, I'm just gonna casually mention the Sealed Vessel track from Hollow Knight... because to be honest, yes I cried to that, and yes I am trash. That song is depressing as hell.
 
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#1
I remember hearing this song for the first time when I was around 10-11. Because of the issues I was going through at home with family, I associated this song with those events. This song felt like that hug I needed after a long day. Now, it's just a sad/nostalgic song I tear up to.



#2
This song is already sad based on the lyrics, but this song was always so deeply depressing to me because of how the singer died. I wish Karen were still alive making music, her songs and her voice have always made me feel a sense of comfort and happiness.

 
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Dizzi

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Thr police every breath you take in memory of my older brother who died at birth of lung complications
 

Castle

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Thr police every breath you take in memory of my older brother who died at birth of lung complications
I gotta admit that's kinda strange, given that the song is about stalking.
 

LegendOfMeesh

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These jams hit me right in the feels, every time, for various reasons. There are really too many on my list, but even this list was narrowed down.. :sweat: Sry


Brighten- Easy to Fall in Love (Acoustic) The number one song that makes me ugly cry, every time. I’ve loved the original song for years and when they recently released an acoustic version.. it was all over for me.



New Found Glory- I Don’t Wanna Know



Dave Matthews and Tim Reynolds, Live at Radio City- #41



The 1975- Somebody Else



Brand New- Jesus Christ



Jason Mraz- I Won’t Give Up. This was my sister’s song for the first dance at her wedding, so now I can’t hear it without getting teary-eyed.
 

CynicalSquid

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This song has been become increasingly difficult for me to listen to. When it came out it was my favorite song on the record. The lyrics are about the guitarist of the band, Tom Searle, and his feelings about his battle with skin cancer. 3 months after the album was released he lost his battle to cancer and it put a lot more weight to the song. However, A little more than a year after this album was released my grandmother was diagnosed with liver cancer and passed away shortly after. I never lost someone important to me before and I never knew someone in my life that got diagnosed with cancer and died from it. I kind of had to drop this song out of my rotation because it became harder to listen to it without relating the lyrics to my grandmother.

 

Shroom

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Gonna try and do a bit of variety in my post, but I tend to like sadder songs. I'll stick to one per artist I like:

The Voidz: Pointlessness


The Strokes: I'll Try Anything Once


Eric Clapton: Tears in Heaven


The Gorillaz: Souk Eye


Queens of the Stone Age: Villains of Circumstance


Soundgarden: Boot Camp


Chris Cornell: Misery Chain
(bit of a cheat here since he sang this song and the one above)

Billy Joel: Vienna


Peter Green: Fool No More


James Taylor: Fire and Rain


The Velvet Underground: Pale Blue Eyes


I could keep going, but I think 11 is enough. All are sad to me for various reasons and are just a number off the top of my head; some are sort of outwardly sad, some have some sentimental reason to me for a time in my life. A good cry to some music never hurt anybody (except maybe the songwriter) and I find it pretty therapeutic. Hope you all enjoy at least one song from this list.
 
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