These are the ones I thought of. The first is about losing love, the second about needing to escape poverty.

YouTube - Bonnie Raitt-I can't make you love me

YouTube - Fast Car - Tracy Chapman

Just another excuse for me to post it for the 14,000th time and he's dead now (only last month) so it should start to gain more fans due to the fickle nature of the populace:

Fickle Nature; as follows,
 

Count me in,:p: or among the fickle, one of the ficklest, whatever.
Thank you for turning me on to John Martyn,:yeah: thank you very much Jackie Boy.

it's just a matter of time with me and Martyn, my favourite is the 60's stuff he did for Island, 'Stormbringer' credited to John & Beverly Martyn in particular

Broken - Lifehouse

In total agreement with Jackhammer about John Martyn, a great loss to music

I think "Disenchanted" and "Cancer" by My Chemical Romance are sad.

"i got id" pearl jam

My favorite Spiritualized song and one of the saddest songs I have ever heard.

My this is a hipster list of mine.
Closer-Joshua Radin
Have You Forgotten-Red House Painters
No Surprises-Radiohead
Dirt In The Ground-Tom Waits
Twilight-Elliott Smith
Doomsday-MF Doom (In a different way than you'd think)
A Lack Of Color-Death Cab For Cutie