Brad Paisley & Alison Krauss - Whiskey Lullaby. About a guy who has his heartbroken by a girl, becomes an alcoholic then kills himself, she blames herself and starts drinking - then she too, commits suicide. Pretty sad.

Sarah McLachlan - Do what you have to do.
Damien Rice - Cannonball.
Coldplay - Fix you.

Blink 182 - Stay together for the kids. Probably not sad for many people, but if you listen to the lyrics and have ever been in that situation, then it's kind of emotional.

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To love is to suffer. To avoid suffering, one must not love; but then one suffers from not loving. Therefore, to love is to suffer, not to love is to suffer, to suffer is to suffer. To be happy is to love; to be happy then is to suffer, but suffering makes one unhappy; therefore to be unhappy one must love or love to suffer or suffer from too much happiness. I hope you're getting this down.

Last Goodbye by Jeff Buckley
I had to listen to this song at least ten times before I would stop crying from it. Very good song though. Preview from amazon: WMP and RealPlayer.

giga! I love tom waits.. his voice is so .. unique

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i love sarah maclachalan. her voice is just so sad to me. especially her songs " i will remember you" and "angel." how bout james blunt's song "goodbye my lover." or michelle branch's "goodbye to you."

i dont know. ive been depressed because i havent "him" in more than a week. im sad cause i miss him so much..

Ray LaMontagne- Empty. This song kicks my ass.

oooooh
i am sad

anything from beck's sea change
nightblindness - david gray
stay - coal
winter - joshua radin
maggie - colin hay
hide and seek - imogen heap
the scientist - coldplay
nobody's fault but my own - beck
fidelity - regina spektor
everybody's gotta learn sometimes - beck
broken drum - beck
that time - regina spektor
i don't know why - colin hay

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People are bastard coated bastards with bastard filling

Coldplay can do some good tearjerkers, alas most of their songs sound depressing anyway.

Deftones - Pink Maggit

KoRn - Daddy

KoRn - My Gift to You

Incubus - Nice to Know You [kinda, not really]

ICP - Under the Moon [extremely sad]

Evanescence - Hello

Coldplay - The Scientist

Chimaira - Nothing Remains [if you can understand it]

Bush - Glycerine