http://www.youtube.com/watch?v=g9LswXpoD8w
http://www.youtube.com/watch?v=vPsRgFQSfSU
http://www.youtube.com/watch?v=x4TLj1Kwo4Q

the big 3

http://www.discogs.com/artist/Aphex+Twin
http://www.discogs.com/artist/boards+of+canada
http://www.discogs.com/artist/freescha

http://www.youtube.com/watch?v=SLJllk-0o6c

http://www.youtube.com/watch?v=zQbdQ96SJWc - cyne

Dust in The Wind by Kansas. It's my ultimate sad song.

Actually, I just listened to Yesterday by The Beatles. That one is pretty good too.

http://www.youtube.com/watch?v=qOtX8TJFXQU
http://www.youtube.com/watch?v=ScwrmGToPyY
http://www.youtube.com/watch?v=dsh9xzTCFRk
http://www.youtube.com/watch?v=o2L8-nODgHI

swapped out the neurosis song because it's just more eerie than sad

Ten Years Gone: http://www.youtube.com/watch?v=J9bP-LbR8u8

Gets me every time. :(

http://www.youtube.com/watch?v=XNSsv86lsok Schindler's list

I was going to say Giles Corey/Have A Nice Life. I'm not surprised you've beat me to it again.

Xasthur is good too. Other sad-ish dsbm/black metal I'd recommend are Peste Noire, Make a change...kill yourself, Weakling, and probably Mystifier too.

As for general sad music, Godspeed You! Black Emperor tends to get me in a certain mood, because it's really ambient and gloomy. The Pine, I Hate Myself, and My Dad Is Dead are really good older emo bands. I could go on but that's probably enough suggestions to get anyone started.

http://www.youtube.com/watch?v=Ep5JAoWP2l4

https://www.youtube.com/watch?v=Hbhx4p9qTts

sad music sux

This song gets me every time - there's a beautiful chord progression near the end - even if you don't understand the subject it's hard not to feel horrible.

http://www.youtube.com/watch?v=0q2ijYcbuxc

(the entire audience was in tears after this performance) General Voroshilov later told the singer, had Stalin still been alive (the song was Stalin's favorite) he'd have immediately been awarded the highest possible honor for artistry.

http://www.youtube.com/watch?v=JfhsRIDh1RQ

Black- Pearl jam

Unrelated but they are coming out with a new album on the fifteenth.

http://www.youtube.com/watch?v=dNjAEjz4eFY

I win

Tf2 has changed...

https://www.youtube.com/watch?v=S6Odu44wYk4

sorry I must :|

http://www.youtube.com/watch?v=Md1lOSvswrM

http://www.youtube.com/watch?v=YmjqO7DD14I

https://www.youtube.com/watch?v=TWcyIpul8OE

Jonny Cash:

Hurt
In My Life
Give My Love To Rose

Pretty much his entire last album gets me :(

http://www.youtube.com/watch?v=8qUvWGb3mG4
http://www.youtube.com/watch?v=BjWfRpfpXJQ
http://www.youtube.com/watch?v=nehYBw__AyQ
feels_felt

;~;

https://www.youtube.com/watch?v=U3i3n8ZTDsc
https://www.youtube.com/watch?v=4Uj2JpvsvX4
https://www.youtube.com/watch?v=jFwIHnbOyrg
https://www.youtube.com/watch?v=TugcoNVboeA
https://www.youtube.com/watch?v=VD8mjrq4vjw

http://www.youtube.com/watch?v=xButjfhZWVU

Probably been linked, but goddamn its good and gets me goosebumps. Perfect for a sad rainy day

"I wear my scars like the rings on a pimp." Love this song.

http://www.youtube.com/watch?v=RS_3pED-wJo

http://www.youtube.com/watch?v=6G2Dya_Eb6g

this song is called sounds of pain and its 20 minutes long
http://www.youtube.com/watch?v=4E-Vk6j_UDQ