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I'm a man of melancholy, a connoisseur of cheerlessness, and a seeker of sobriety. I'm not a sad person, but for some odd reason I like sad songs. So I propose a game.

You know the drill: Spoiler buttons make the mods happy.

No song quite captures the spirit of hope, defeat and loss as well as Fast Car.

A Better Place, A Better Time

Weather Storm.

I picture sadness itself when I listen to that as a solo piano.

The mods smile frown upon this thread.

Long song, odd time signature, good for those who are perpetually friend zoned.

"Sometimes a life that seems hard to take
Is soothed for a while by an old friend
Leaving a bad need in its wake.
Sad, how some friendships never, ever seem to end.

"Well, all of my heroes up and died.
Songs and a dream are left for me.
What did them in, not suicide
Just a lengthy friendship and a dream of how it could be."

Luv (sic) Part 5 by Nujabes and Shing02. It's not the saddest song I know, but it's what I'm listening to right now and it's definitely very melancholy. Not to mention a fantastic song.

I have two to share

This plays in the Watchmen Director's Cut, when Hollis Mason fights a group of thugs and..Well I won't say anything else,you can watch the video here

Here's the saddest album I know of. Only click if you have an hour to spare.

I have a few that can be sad, depending on your interpretation of them. I'd say bittersweet is a better term.

And the objectively saddest of all:

This song nearly moves me to tears every time I hear it. Call me a sucker for war drama, but it really gets me somehow.

Surprised no one's posted this

In all seriousness though this one's probably the most depressing for me

This song has been linked to a large number of suicides, probably the saddest song ever written.

Fun fact: This is one 27 samples of music included on the Voyager Golden Record, launched into space in 1977 to represent the diversity of life on Earth if any other living life form ever finds it. It was chosen as the human expression of loneliness.

Needs moar doom metal.

About half of the Kingdom Hearts soundtrack

I have two songs, both (predictably) from Radiohead.

The second song was actually written for Baz Luhrmann's Romeo + Juliet, and it plays over the credits. After they die.

You're welcome!

I know that feel ,bro.

So many to choose from, right?

if you want to cry more, watch the movie. Will make you cry man i swear.

Fun fact: This is one 27 samples of music included on the Voyager Golden Record, launched into space in 1977 to represent the diversity of life on Earth if any other living life form ever finds it. It was chosen as the human expression of loneliness.

About half of the Kingdom Hearts soundtrack.

Damn straight. The ending with Kairi calling to Sora still gives me the feels.

I second that motion, it's a depressing story through and through.

I think this is the saddest thing I got:

Even then, it's probably not that sad. I tend to steer away from really depressing sounding stuff so my options are pretty limited. I don't think I actually have anything else that sounds downbeat and mellow. I'm always going for energy.

But that one got into my playlist for the impressive atmosphere.

Vsauce!

This… Just like old times, eh?

Fuck you.

But seriously. It's Hard to Say Goodbye – Micheal Ortega.

Verbose, those lyrics seem more like a friend's death than a description of the friend zone. Maybe that's just me though, I haven't gotten to that one yet.

Mad World. And the Gary Jules version, not Tears for Fears.

It's beautifully depressing. I find it sad because every single line in the song describes me.

cries in corner

A lot of his songs are sad and dark.
RIP Johnny Cash.

I have no idea why, but the end song for Adventure Time always gets to me.

I know, I know. Nobody has any idea what most of the lyrics are about.
Eddie once said it was about his friend, Tim Ledbetter, receiving a yellow letter in the mail about how his brother had died in the first gulf war.

There used to be a rumour that this song was about the guitarist's brother being killed in a fire when they were children. That was fake. He never had a brother. Still, the song is really sad. Almost has a tragic feel to it.

Unfortunately, it gets a bit too obvious in the chorus, but the rest is quite compelling.
"What Sarah Said"
by Death Cab for Cutie

It's basically about sitting in the hospital while waiting for his friend to die.

It's just so sad. Justin Bieber, world's worst artist, teamed up with Nicki Minaj, the gibberish rapper.

Some called it the official end to good music. Some called it the beginning of the end. Who knows?

Oh gods, Death Cab for Cutie. That reminds me of a song I should post.

The song is beautiful, the video is incredible, and I want to hold the riff towards the end and never let it go.

Another extremely sad one, especially if you're into 8-Bit/Chiptune, is

This song, using typical 8-bit (or 16-bit, unsure) conventions has enough emotional weight to blow most modern songs out of the water.

Steely Dan – Home At Last

I once literally cried to this song. No idea why, but because of that, I'm gonna go ahead and say it's the saddest song I know.

Or click: How do I live

Or click: How do I live

Nicholas Cage, 10/10

Another really great one by Death Cab:

In b4 Dead Island theme.

Oh. Yeah.

Don't click that if you don't want liquid feels injected into your brain.

This is so neat.
Every important part of the anime had this song playing, it is beautiful and calming but sadding. Two brothers searching for a way to get themselves back to normal after they attempted of bringing back some one they hold dear which did cost them dearly as well.

If anyone finds that song they use in RIP Videos, please, let me know.

AHEM

INB4 SAD VIOLIN

This is pretty melancholic, yet oddly calming:

https://www.youtube.com/watch?v=3MC-FLXkg3M