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What's the saddest song you ever listened to

Tough question. "Was It A Dream?" by 30 Seconds to Mars comes to mind, but that could be because I listened to it a lot while I was going through a bit of a rough stretch in my life a year or so ago. A more recent example would probably be "Rose Of Sharyn" by Killswitch Engage. Both are garbage choices, I know, but that's all that's coming to mind at the moment... I'll get back to you when I think of a more definitive answer.
 
Mocking bird by Eminem
I don't really like listening to sad music
 
Hikari no Naka e by Maaya Sakamoto (one of Hitomi's chara songs from Escaflowne, not that I've actually watched the anime :p)

Lyrics translation:
If I let go of your hand clasped in mine,
with that, it would all probably come to an end right now.

What I wanted to know, and even what hurts me-
even those were left undone.

Even though I should want to wish
for you to find happiness,
I can't, I'm too immature.
I wipe the tears, but they still keep flowing.

Sayonara.
I love you
more than anyone else.
Even more deeply than the sky.

Don't cry.
We'll meet again, right?
But not being able to see you
is something that only I know about.

This fate that we've chosen...
someday you too will understand its true meaning.

The treasure of memories that we've made
will always live on deep inside my heart.

I thought it was a beautiful thing,
the word called hope.
In an almost painful embrace,
I'm looking up at you.

Arigatou.
I love you
more than anyone else.
Even more strongly than dreams.

Hold me.
Don't let go.
But don't utter
even a single thing...

Don't cry.
I love you.
Even though we're separated far apart,
I can still live with you.
 
Kate Havnevik - "Grace"

If I'm sad/heartbroken and listen to that song, it makes me cry. Other music from GA too (I wish I still watched the series... it was awesome)
 
Finally thought of it. :p I'd have to go with "Hikaru Michi (The Shining Road)" by Aya Hiroshige. It was used as the second ending theme to Sonic X, I believe. Even without knowing the lyrics it's very emotional, and when you do, well, that just makes it even more so.
 
Brick by Ben Folds Five.

And All That Could Have Been by Nine Inch Nails.

But the only song I've ever cried to is, Lilly Was Here by Candy Dulfer because it was played at my Nan's funeral last year. Still can't listen to it a year and a half later.
 
Peter Schilling's Major Tom- just read the lyrics

Standing there alone,
the ship is waiting.
All systems are go.
"Are you sure?"
Control is not convinced,
but the computer
has the evidence.
No need to abort.
The countdown starts.

Watching in a trance,
the crew is certain.
Nothing left to chance,
all is working.
Trying to relax
up in the capsule
"Send me up a drink."
jokes Major Tom.
The count goes on...

4, 3, 2, 1
Earth below us
drifting, falling.
Floating weightless
calling, calling home...

Second stage is cut.
We're now in orbit.
Stabilizers up,
runnning perfect.
Starting to collect
requested data.
"What will it affect
when all is done?"
thinks Major Tom.

Back at ground control,
there is a problem.
"Go to rockets full."
Not responding.
"Hello Major Tom.
Are you receiving?
Turn the thrusters on.
We're standing by."
There's no reply.

4, 3, 2, 1
Earth below us
drifting, falling.
Floating weightless
calling, calling home...

Across the stratosphere,
a final message:
"Give my wife my love."
Then nothing more.

Far beneath the ship,
the world is mourning.
They don't realize
he's alive.
No one understands,
but Major Tom sees.
"Now the light commands
this is my home,
I'm coming home."

Earth below us
drifting, falling.
Floating weightless
coming home...
Earth below us
drifting, falling.
Floating weightless
coming, coming
home...
home.....
 
Live In The Sky-T.I. feat. Jamie Fox
Some of the lyrics really have a lot of meaning to me >.>
 
There are a few that are sadder, but I'll have to go with "Bright Eyes" from the Watership Down film, if anything because it practically haunted me since I was a child. It took until I was in eighth grade to 'rediscover' it- I hadn't remembered what the movie was, or most of the movie in general, since I was so little. What I did remember was the song and that scene.

Oh yeah, and the song at the end of The Plague Dogs film. I can't even stand to hear it anymore. Doesn't help how the movie ended when they started playing it. Now I was nearly sobbing at that.
 
Miki-Fan said:
Peter Schilling's Major Tom- just read the lyrics

Standing there alone,
the ship is waiting.
All systems are go.
"Are you sure?"
Control is not convinced,
but the computer
has the evidence.
No need to abort.
The countdown starts.

Watching in a trance,
the crew is certain.
Nothing left to chance,
all is working.
Trying to relax
up in the capsule
"Send me up a drink."
jokes Major Tom.
The count goes on...

4, 3, 2, 1
Earth below us
drifting, falling.
Floating weightless
calling, calling home...

Second stage is cut.
We're now in orbit.
Stabilizers up,
runnning perfect.
Starting to collect
requested data.
"What will it affect
when all is done?"
thinks Major Tom.

Back at ground control,
there is a problem.
"Go to rockets full."
Not responding.
"Hello Major Tom.
Are you receiving?
Turn the thrusters on.
We're standing by."
There's no reply.

4, 3, 2, 1
Earth below us
drifting, falling.
Floating weightless
calling, calling home...

Across the stratosphere,
a final message:
"Give my wife my love."
Then nothing more.

Far beneath the ship,
the world is mourning.
They don't realize
he's alive.
No one understands,
but Major Tom sees.
"Now the light commands
this is my home,
I'm coming home."

Earth below us
drifting, falling.
Floating weightless
coming home...
Earth below us
drifting, falling.
Floating weightless
coming, coming
home...
home.....
Click to expand...

Wow, it's just like David Bowie's Space Oddity but not as good.
 
.-. There's a lot of songs that I find sad these days... However... one that affects me greatly is one that's off of the Pokémon: The First Move Soundtrack -- 'If Only Tears Could Bring You Back' by Midnight Sons.
 
Shiay said:
.-. There's a lot of songs that I find sad these days... However... one that affects me greatly is one that's off of the Pokémon: The First Move Soundtrack -- 'If Only Tears Could Bring You Back' by Midnight Sons.
Click to expand...
For some reason, this song moves me a lot more when I simply read the lyrics to myself than when I actually hear it played. I think it's because when I read them, I always pictured the song from a woman's point of view rather than a man's, and when I hear a male voice singing them it just doesn't hit me as hard.

Yeah I'm weird, I know.
 
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