that song "when i was 17"...forgot who it was by.
but simpsons ripped it off...

I always "Four Seasons In One Day" by Crowded House to be a pretty darn sad song...

"Asleep"
 

Jeez, there are so many great songs to just sit and wallow with.

One that gets me every time is "Asleep" by the Smiths.

Hope nobody suggested that already.

At 17 I think was by Janice Ian initially.

Oh yeah, I remember that Song and the Simpsons knock off of it...

When I was seventeen, I drank a very good beer...

Morphine - Saddest Song
Great imagery my friend

sad
 

Andrew McCahon sucks, but Konstantine is really sad. Makes my eyes burn.

So,
Konstantine - Something Corporate
Sleeper 1972 - Manchester Orchestra
Jesus Christ - Brand New ("Jesus Christ I'm alone again, so what did you do
those three days you were dead? 'Cause this problem's
gonna last more than the weekend.")
Oh, Deceiver - Right Away, Great Captian
No Name No. 5 - Elliott Smith
Why I'm So Unhappy - Dntel
This Blackest Purse - Why?
A Ghost Beneath the Tower - The Winston Jazz Routine
My Sundown - Jimmy Eat World
Your Ex-Lover Is Dead - Stars
I've Been Eating For You - Bright Eyes

I approve of about half your list and your username just makes me laugh.

Nothingman by Pearl Jam... got it on right now and it nearly breaks my heart in two every time I hear it...

Said the whale - Curse of the currents/from autumn to ashes - chloroform perfume
Works every time :}