Originally Posted by HackedUpForBBQ
Opeth - To Bid You Farewell
I'm with you 100% on that one. I'll take it a step further and say it's the best song Opeth has ever written.
Originally Posted by BTBAM310
NIN - Something I Can Never Have
Agree, but I think there have been sadder NIN songs. "A Warm Place," for example, I find to be incredibly sad, even though I think Reznor intended for it to have the opposite effect. Also, "What If We Could" on the Reznor/Ross album, maybe if not necessarily sad, is extremely sobering.
Originally Posted by MetalIsArt
Together with Billy Joel, one of the best singer-songwriters imho.
Absolutely, and there are so many to pick from. As Chuck Klosterman said, every one of his songs — including the happy ones — are ultimately about loneliness.
A few more that come to mind:
Bob Marley - Redemption Song
Agalloch - Our Fortress Is Burning... II - Bloodbirds
Permixtio - Melancolia in Requie
Nada Surf - If You Leave
Caspian - Last Rites
Sorne - Coyote
The Beatles - While My Guitar Gently Weeps (the acoustic version by Harrison, that almost sounds like it was recorded live)
Metallica - Fade to Black; this song left quite the long-lasting impression on my teenage self, and it's still incredibly powerful to this day.
Alcest - Sur L'Ocean Couleur De Fer; absolutely heart wrenching atmosphere in this song, maybe the saddest song atmosphere-wise I've ever heard.
Avenged Sevenfold - So Far Away; pure channeled emotion from the death of childhood friend and bandmate, Jimmy Sullivan.
Borgne - All These Screams Through Me; oppression at its finest right here. From what I can tell the lyrics are about an invalid seeking to find some meaning in life, but she finds herself in circumstances that make it impossible. The crushing weight of the song, and especially the piano outro, reinforce her hopelessness.
Godspeed You! Black Emperor - [Antennas to Heaven...]; Two of the most emotional minutes of music. Bleakness and dread mixed with a touch of hope, with a tragic finish. Songs that convey multiple emotions simultaneously are the best kinds of songs.
Also a number of Scorpions ballads, notably Lady Starlight.
And Mabel Faletolu's "Gandalf Falls" soundtrack.