The bestest sadest songs in the whole world.

[Sightless]

You wish you were.

 

[Kijan]

http://www.youtube.com/watch?v=ROKcr2OTgws - don't think it's sad per se... but I think it's quite melancholic.

 

[XboxLiveLover]

not sure if its been posted yet but pete yorn lose you:

http://www.youtube.com/watch?v=3wabdSbowXQ

EDIT:

I can't forget about these two songs as well:

2Pac-Changes
http://www.youtube.com/watch?v=Wikrv81Fh3I

Puff Daddy-I'll be missing you
http://www.youtube.com/watch?v=mM0-ZU8njdo

 

[UghRochester]

When I posted Metallica's music vid for "One," I forgot it had a neat solo towards the end. So, I'm learning that bit by bit
http://www.youtube.com/watch?v=TaG3NkzdXb0

Oh and here's another sad song. don't know if it was posted but it's "Mad World" by Gary Jules (perhaps you best remember it from the Gears of War trailer)
http://www.youtube.com/watch?v=D1Nq086Q ... re=related

 

[cyberjim2000]

I don't usually listen to sad music but here's an oldie that's short and sweet:

http://www.youtube.com/watch?v=stwt_ew6Bac

 

[segageek]

ive been pretty down latley one of the best sad song


http://www.youtube.com/watch?v=yhX6Sxba ... re=related