Saddest song you have heard
 

That's the Way by Led Zeppelin

oh god, almost makes me cry whenever I listen to it.

Particularly the version on How the West Was Won

"Mad World" that song from Donnie Darko

by Gary Jules

Yeah, Mad World by Gary Jules is definitely up there. Even the Tears For Fears version is kinda depressing.

the christmas shoes

lol awesome dude

"My Humps" by Black Eyed Peas

It saddens me to think of popularism invading hip-hop culture, but...

Seriously, Aphex Twin's "Rhubarb" is as mellowing as it is melancholy.

"Let's not shit ourselves" and "waste of paint" by bright eyes

"She's Leaving Home" by The Beatles

IAM - Un cri court dans la nuit

Who let the Dogs out?

It saddens me that the dogs were let out.

"We Won't Get Fooled Again" has specific undertones to me which I find to be more depressing than most shit. It's almost like the whole "The Wall" Neverending cycle (Isn't this where we came in) in terms of "Meet the new boss, same as the old boss."

Then again, it's not so much a sad song as much as a cerebral depression based upon the sad reality it mentions. So...

How to dissappear completely--Radiohead

When the Tigers Broke Free- Pink Floyd

Ever Rose has it's storm

duh! the name of that song is Every Joe has some porn

Whiskey Lullaby - Brad Paisley and Allison Krauss

"Cold Wind" By the Arcade Fire and "Breathe Me" by Sia immediately spring to mind.

Nothing Compares 2 U -- Sinead O'Connor

Tears in Heaven -- Eric Clapton

Down in a Hole -- Alice in Chains

Add every mellow drug referenced AIC song to the list as well.

Last Train Home - Lost Phrophets, I have my reasons

Not being sarcastic here, but 'Are You Sad' by Our Lady Peace almost makes me cry when I hear it, and thats when nothing bad has happened.

Styrofoam Plates - Death Cab for Cutie

Gary Jules - Mad World
Sublime - Poolshark
The Smiths - Last Night I Dreamt That Somebody Loved Me
Death Cab For Cutie - Styrofoam Plates
Elliott Smith - Fond Farewell
All Time Quarterback - Send Packing
Glassjaw - Everything You Ever Wanted To Know About Silence
Smashing Pumpkins - Daphne Descends
Weezer - Butterfly

Suck a racehorse's cock with Heinz Tomato Ketchup

inmates by the good life

oh and "album of the year": by the good life

I dunno, I listen to a fair bit of melancholy music, it's hard to really choose one. :$

• "Night And Day" - The Good Life
• "How To Disappear Completely" - Radiohead
• "Motion Picture Soundtrack" - Radiohead
• "No Lies, Just Love" - Bright Eyes
• "After The Movies" - Cursive
• "This Song Brought To You By A Falling Bomb" - Thursday
• A lot of Sigur Ros stuff
• "Fight Song" - The Appleseed Cast
• "This Place Is A Prison" - The Postal Service
• "Styrofoam Plates" - Death Cab For Cutie
• "Fred Jones Pt 2" - Ben Folds
• "The Ballad" - Millencolin
• "El Torrente" - Minus The Bear

...all of those yank at the ol' heart strings for one reason or another.

Dear Momma- 2 Pac

Boston's "More than a feeling" always does it for me :(

There's something about Maps by the Yeah Yeah Yeahs that always makes me feel like shit

I think Hurt by Johnny Cash, but with the video.

Also Untitled #1 by Sigur Rós.

I think that Hurt by Johnny Cash is a really sad song if you really listen to the lyrics.

THe video is also good for that song

Yo Cash didn't write those lyrics.

Explosions In The Sky - Glittering Blackness

no he didnt but he made a change

Yeah, I think he took out "shit" because geezers are offended by cuss words. What's your point?

Yeah seriously. Shut the fuck up Tidus