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Saddest Songs

"Whiskey Lullaby" - Brad Paisley and Alison Krauss
 
White Flag- Dido
Happy Home- Garbage
I Don't Know If I Should Stay- Alexz Johnson
Adam's Song- Blink 182
The Ocean- The Bravery
We Might As Well Be Strangers- Keane
Early Winter- Gwen Stefani
Lemon- Katy Rose
Hear You Me- Jimmy Eat World
Pieces- Sum 41
 
Tim McGraw- Please Remember Me

Leann Rhimes- Probably Wouldn't Be This Way
 
Jeff Buckley's Hallelujah takes that title HANDS DOWN. The chord progressions of that song can make even frolicking puppies seem depressing

Notable Runner's Up
Strange Fruit- Billie Holiday
The River- Bruce Springsteen
Under The Bridge- Red Hot Chilli Peppers
Goodbye My Lover- James Blunt
 

Motion picture soundtrack — Radiohead


I'm not sure if I would pick that or "How to Disappear Completely"

But my other picks would be:

Patty Griffin - Top of the World
Sia - Breathe Me

I totally agree with metman
Antony and the Johnsons - Hope there's someone
 
Draconian - She Dies
Draconian - Death Come Near Me
Draconian - The Cry Of Silence
Draconian - The Dying
Draconian - It Grieves My Heart

basically most of their songs...
 
Sia - Breathe Me
Portishead - Roads
The above two make me sad because a friend put them on a mixed cd, and I knew she'd been feeling incredibly depressed in the previous few months, to the point where we were worried we'd lose her, so listening to these songs it almost felt like she was singing it herself.

Sigur Ros - Vaka (untitled #1) (just because it's so damn beautiful.. but also because of the sad filmclip)
Fiona Apple - Oh Well (the way she sings "Oh well" breaks my heart everytime I hear it)
Sarah Blasko - I could never belong to you
Bjork - New World (because of what has happened to Bjork's character in Dancer in the Dark)
 
The Fray - How to Save a Life
Keane - She Has No Time
Aerosmith - Amazing
Dave Matthews - The Dreaming Tree
Coldplay - Amsterdam
Jet - Shine On
Matt Nathanson - Sad Songs (lol. I just had to include it.)
OAR - James
All-American Rejects - It Ends Tonight
Guster - Rainy Day

Thanks for putting me in a depressing mood lol.
 
Joni Mitchell - Blue
Nina Simone - Little Girl Blue
 
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