Hard times call for desperate measures *tearing intensifies*

How the hell is Tears in Heaven by Clapton not on this list?

My favorite sad song is “Creep” by Radiohead.

What about "follow you into the dark" by death cab for cutie? That is a beautiful sad song.

Gary come home

"Season's in the Sun" sung by Terry Jacks?

I was just listening to Everybody Hurts

I love that Rival Sons made the list.

'look on down from the bridge' by Mazzy Star is about a woman who is standing on a bridge, trying to gather the courage to commit suicide. It is beautiful and something you can listen to anytime.
'asleep' by the Smiths is also about suicide and makes me extremely depressed just to listen to, especially the last minute or so. I almost killed myself to this song once.
It got too personal. I might add more but now I feel like crying

Down in a hole by Alice In Chains

Last Kiss by Pearl Jam was the first really sad song I ever heard

The Dance by Garth Brooks

Into the West by Annie Lennox

Asleep by The Smiths, when you're sad and wanna cry this'll make you cry

Cat's in the Cradle by Cat Stevens always makes me sad

Binks' brew

Glass Eyes- Radiohead. This is the kind of song where you bury your head in your pillow and weep.

Red Like Roses part 2 by Jeff and Casey Lee Williams

What about 'Do I Wanna Know ? ' by the arctic monkeys? It made me cry because I'm just that lonely.

No Mad World by Gary Jules? Seriously?