Hospice, hands down. Not a glint of light on that album.

Every Elliot Smith album.

The Smiths' debut always leaves me feeling slight suicidal after a spin

I agree with Hospice and anything by Empire Empire (I Was A Lonely Estate)

I'll add The Saddest Landscape - You Will Not Survive. Very emotional, extremely sad, but a great listen.

Also Mansions - New Best Friends.
Which to me is an album you can only enjoy when you are extremely miserable. If you listen to that album in a good mood... well you should never listen to that album in a good mood.

Yeah, Suffer Little Children is as dark as you can get.

Here are some more additions...
Faith - The Cure
Berlin - Lou Reed
The Wall - Pink Floyd
Nico's solo albums always struck me as being rather sad, as does a lot of Leonard Cohen's work.

This is only a song, not an album, but it is one hell of a sad song.



In a way, And Don't the Kids Just Love It is a sad album.

Makes me cry every time... There's no way an album can get sadder than this...

http://upload.wikimedia.org/wikipedi...ica_-_Load.jpg

But that's not the saddest, there's worse... However, nothing can get sadder than this one.

http://upload.wikimedia.org/wikipedi...ica_Reload.jpg

oh wait...

http://upload.wikimedia.org/wikipedi...stanger_lg.jpg

I've got a few that are really depressing to me, that may not be for other people. First and foremost:

http://www.tinytim.org/images/complete-reprise-cd.jpg

This one may be especially strange to some (many? most?), so allow me to explain: I always listened to a little bit of Tiny Tim for the novelty. You know - chilling and listening to "Livin' In the Sunlight, Lovin' In the Moonlight" or "Tiptoe Through the Tulips", appreciating the strangeness, whimsy, and fanciful nature of the tracks. I was looking for a good "pick-me-up" album after a rough stretch, and chose to download this thinking, "Oh, joy! This is ukulele-laden bliss, and it will pick me right up!" Perhaps it was just my mindset at the time, but that wasn't the case. I found that it made me overwhelmingly sad. What I saw the album for was this: Tiny Tim adopted this persona deliberately to have the naivete and wide-eyed wonder that a child has. It's the world as seen through the eyes of a child, is basically what I'm saying - you probably gathered that, but yeah. In addition, even the covers took on a whole different effect for me, listening. Anyway, certain tracks especially troubled me, as I saw the album from that perspective. Several of these will be included below.




And, Hell, even:

StarSailor - Love Is Here
 

Pretty much every song on this album is about soemthing heartwrenching.

But still one of my favourite albums.

Probably one of the best break up albums ive ever listened too ha.