I second this...

John Wayne Gacy, Jr. - Sufjan Stevens

Take some drugs and listen to anything by the Doors and you will want to pull the trigger!

Pink Cigarette by Mr Bungle, better for if you were dumped though.
http://www.youtube.com/watch?v=TwWQYg7aS5o

Nice David Lynch style video too.

[This message has been edited by mjfrog (edited 12/13/2008 6:30p).]

Anything with vocals by Kurt Coblam...eerrr Cobain.

"I want so much success it'd blow my head off"

OK so he never said that, but to try an achieve so much that it would depress you that much.....

PULEEEZE.

Disappear by Dream Theater.

St. Patrick's Day -John Mayer

I cant believe the only Smiths song in this thread is Girlfriend in a Coma which is tongue in cheek anyway. how about "I Know Its Over" which starts & ends:
Oh Mother I can feel the soil falling over my head...

"Wichita Lineman" by Glen Campbell

"Pink Moon" by Nick Drake

"The Needle and the Damage Done" by Neil Young

Heal Me, Im Heartsick - School of Rock SoundTrack (No Vacancy)
Broken - Cross Canadian Ragweed
Life Aint Always Beautiful - Gary Allan (first song after his wife committed suicide)
Cab - Train
Hate Me - Blue October
It aint easy being me - Chris Knight
Dead Flowers - Townes Van Zandt



[This message has been edited by truger83 (edited 12/17/2008 8:51a).]

Townes -- "Marie"

quote:

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"Pink Moon" by Nick Drake

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the album is dark, but not sure how this song is depressing. depending what you think the pink moon stands for, it still doesnt seem as depressing as something like Big Star's Holocaust.

Anything by Polyphonic Spree...

Ok, not really...