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Y'know when i first came to netalive over two years ago, the first post i made was referring to evanescence, my immortal, i think.
It is the ultimate depressing song for me. Though if you really want to hit the spot, you might need to be more specific. Give me a better idea of what sort of theme your on to and i might be able to help more.
Mad World - Gary Jules.
Gotta be one of the sadest songs i know, especially when listening to the lyrics.
And I find it kind of funny
I find it kind of sad
The dreams in which I'm dying
Are the best I've ever had
I find it hard to tell you
I find it hard to take
When people run in circles
It's a very, very
well yeah, sometimes speaks right from my soul (apart from me not being suicidal ;) )
"The wise have always said the same things, and fools have always done the opposite"-Schopenhauer
Chris Smither's "No Love Today" pretty much takes the cake for me right now. The Arcade Fire's "My Body is a Cage" is another really good one, and a couple other songs from that same album ("Bad Vibrations/Black Wave" and "Intervention" come to mind) will definitely make it on my top twenty most depressing songs list. If you're looking for post-apocalyptic black hole of despair type depressing, the first half or so of Godspeed! You Black Emperor's "Dead Flag Blues" is certainly there. It features the actor who played The Seargent in The Big Red One doing this very weird monologue that reminds me of Chief Broom from One Flew Over the Cuckoo's nest. Only creepier but slightly more sane. Also, there's a fistful of Jeff Buckley and Radiohead songs that come to mind, but that's really more of a buffet than a specific dish, so you could just go wild with their respective discologies.
I'll believe in anything if you'll just believe in anything