The Saddest Songs Ever

It's actually my good friend's obsession with him at the moment... and the cheese. Direct quote: "If you like Nick Drake, then you'd love Joshua Radin." You can imagine my disappointment upon hearing him.
 
Pantera - Hollow
Damien Rice - The Blower's Daughter
Kansas - Dust In The Wind
Billy Joel - And So It Goes
Dave Matthews - Gravedigger
R.E.M. - Everybody Hurts

Just to Name a few
 
womp womp womp!!! so sad songs hey... just the kind of music io relate to!
there all sad to me for one reason or another but i dunno if they are to you or not!!.. gave it a shot!

aerosmith -don't want to miss a thing
appleseed cast - steps and nurabers
bayside - just enough to love you
ozzy osbourne - goodbye to romance -
cold - a different kind of pain/bleed/sad happy
pearl jam - last kiss
skid row - i'll remeraber you
bonjovi - always/never say goodbye
fleetwood mac - song bird
elton john - daneil
duran duran - ordinary world
 
Yesterday- Beatles
Last Goodbye- Jeff Buckley
Lover, You Should Have Come Over- Jeff Buckley
Butterfly- Weezer
A Day in the Life- Beatles
Dust In the Wind- Kansas
Scenes From an Italian Restaurant- Billy Joel
The Great Below- Nine Inch Nails
Do Re Mi- Kurt Cobain
While My Guitar Gently Weeps- Beatles

Mr. Blue Sky, of course- ELO
 
Blech to all of this. Every one of those makes me sick.

Also,

Violent Femmes - Gimme the Car

Poor guy, he just wants the car so he can pick her up, get her drunk, make her cry, get her high, make her laugh, and make her shhhhhh. And then touch her all over her body, in lieu of her touching him all over his body. Come on dad.
 
Gary Jules-Mad World
The tone of it is just incredibly sad, and depressing.....
although I love it

Sarah McLaughlin-Angel
I always think it's a meditation on death,
and when she sings, 'may you find some comfort here',
it's so sad, because I think there are so many people out there who wonder if death is more comforting than life.
I'm not really suicidal, but sometimes I do wonder that myself.
 
It's Alright, Ma (I'm Only Bleeding)-Bob Dylan
The last three lines are genius. It's not really sad in a conventional sense, but I find it deeply affecting.
And if my thought dreams could be seen/they'd probably put my head in a guillotine/but it's alright ma/it's life and life only.
 
Haven't read through all of the thread, but has anyone mentioned Dolly Parton's "Me and Little Andy"? What a tearjerker. :(

Sarah McLachlan's "Angel' is rather sad and gloomy- but there's also a strange, beautiful quality to it.
 
The Flying Burrito Brothers - Hot Burrito #1 (though #2 is also killer).

Cash's cover of "Hurt" is always brought up, but "I See a Darkness" is the one that gets to me.
 
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