The Saddest Songs Ever

lucy- skillet
jolene- zac brown band
what sara said- death cab for cutie
miserable at best- mayday parade(mediocre band, great song)
whiskey lullabye- brad paisley and allison krauss
cats in the cradle- any artist that has done it
rescue me- buckcherry
almost easy- avenged sevenfold
most of the alkaline trio's stuff from from here to infirmary and mabey ill catch fire
(the last three are for mostly personal reasons)
 
Songs which make me incredibly sad, more often than not:

Trey Anastasio - A Case Of Ice and Snow
Nirvana - You Know You're Right
Don McLean - Vincent
Julia Nunes - Stairwell
Sarah Brightman - Dust In the Wind
Queen - Dear FrienRAB
Sarah Blasko - Goodbye Yellow Brick Road
Elton John - The Last Song Between a Father and His Son
Emiliana Torrini - If You Go Away
Imogen Heap - Hide and Seek
Elliott Smith - 2:45 AM
Joni Mitchell - River
Leonard Cohen - Famous Blue Raincoat
Tom Waits - Tom Traubert's Blues
Richard & Linda Thompson - The End Of the Rainbow
Tim Buckley - Morning Glory
 
Oh, definitely; overexposure and inappropriate context can really kill a great song. That's one reason why I don't listen to the radio/watch TV, etc.
 
Joy Division- The Eternal

I have not heard a song more depressing then this, and knowing the story of the lead singer makes is worse.
 
John Lennon- Real Love
Elliot Smith's music.
The topic may not be sad...but, when you start thinking about how he died, ugh, it is sad and creepy.
Hari Kari.....*shudders*
 
Any of the last four tracks off of Joy Division's 'Closer' get my vote. Nick Cave's 'Lay Me Low' is a pretty sad song too. Other than those, Oasis' 'Sad Song' pretty much goes without saying
 
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