The Saddest Songs Ever

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Kind of an odd choice considering some of the generic choices people have been listening, but this song is the perfect example of the tragic romance... of video game characters.
 
All right, 2 things to get out of my chest, Led Zeppelin did not write Babe I'm Gonna Leave You, Anne Bredon did and it was first covered by Joan Baez (although some people hate that version). Neither did Jeff Buckley write Hallelujah, although his cover is excellent, Leonard Cohen wrote it.

As for my choices:

Tears In Heaven, The Circus Has Left Town - Clapton (come on, songs about his dead 5 years old son? you can't beat that kind of sadness)
If It Be Your Will - Leonard Cohen (although some of the previously mentionned choices are just as adequate)
And a couple of Tom Waits, for sure, Road To Peace and Ruby's Arms are the first that come to my mind.
 
"Paint It Black" by the Rolling Stones is, in my opinion, the best song about grief ever made. The lyrics are powerful, evocative and poetic...no simple, generic sentimentality.
 
Fast Car by Tracy Chapman is awesome.

One song that always gets me is The Background by Third Eye Blind. Me and my ex dated for over 2.5 years and it was a really passionate, but really messy relationship. This song would always make me cry like a pussy.

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I think its about someone passing or something (not really sure to be honest)... but a few lines always got me crying for months after we were done.

"The plans I made still have you in them"
"and im hangin on your worRAB like I always used to do
"I felt you long after we were through:

This song just really spoke to me at the time, it felt like a lot of what I was going through. **** now I'm probably gonna start crying again lol
 
Where do I begin!
_Follow you into the dark -Death Cab for Cutie
_Nothing Better- The Postal Service
_ I Never Came- Queens of the Stone Age
_This Place is a Prison- The Postal Service
_The Water-Feist
 
I don't really know his music much beyond the singles but "Brick" is certainly a hell of a depressing song. I didn't even realize how depressing until someone explained what it was about to me.
 
I find "Alone" with Celine Dion's rendition very sad yet powerful. Also Anne Murray's A Broken Hearted Me makes me really sad
 
Forget Her - Jeff Buckley
It's Cool, We Can Still Be FrienRAB - Bright Eyes
Heaven Beside You - Alice in Chains
The Promise - Bruce Springsteen
Society - Eddie Vedder
True Love Waits - Radiohead
Tangerine - Led Zeppelin
Hurt - Johnny Cash's version
 
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