Speaking of Radiohead, Thom Yorke's duet with Bjork on her song "I've Seen It All" is one of the most depressing songs ever.

Also, the Grandaddy song "The Warming Sun" is a serious downer. In fact several songs off of Sumday are pretty depressing.

My top 5 favorite wallowing songs:

1. A new low in getting high- Brian Jonestown Massacre
2. Last night I dreamt that somebody loved me- The Smiths
3. Wickerman- Pulp
4. Seems so long ago, Nancy- Leonard Cohen
5. The parting glass- The Pogues

Hope it helps
Misery loves company


Noel

The song ends with "I will see you in the next life." I take that as a more hopeful/optimistic feeling myself, but idk.

Pyramid Song - Radiohead
Life in a Glasshouse - Radiohead.
Actually, pretty much anything by Radiohead.

Part Five – On a Downer: 60 Songs for Long Dark Night of the Soul (Q Magazine's 1010 songs you must own)

o 10:15 Saturday Night – Cure
o Atmosphere – Joy Division
o Black Hole Sun – Soundgarden
o Blue Moon – Elvis Presley
o Blueski – Underworld
o Born to Lose – Ray Charles
o Climbing to the Moon – Eels
o Country Feedback – R.E.M.
o Cry Me a River – Justin Timberlake
o Crying – Roy Orbison
o Don’t Let Me Be Misunderstood – Nina Simone
o Future – Leonard Cohen
o Ghosts – Japan
o Goin’ Back – Dusty Springfield
o Goodbye to Love – Carpenters
o Helpline Operator – The The
o I Can’t Stand the Rain – Ann Peebles
o I Didn’t Mean to Hurt You – Spiritualized
o I Don’t Know – Beastie Boys
o I Just Don’t Know What to Do with Myself – Dusty Springfield
o I See a Darkness – Johnny Cash
o I’m on Nights – Richard Hawley
o I’m So Lonesome I Could Cry – Hank Williams
o In the Wee Small Hours of the Morning – Frank Sinatra
o Jealousy – Pet Shop Boys
o Last Goodbye – Jeff Buckley
o Live to Tell – Madonna
o Losing My Mind – Liza Minnelli
o Lover Man – Billie Holiday
o Martha – Tom Waits
o Naufragio – Ibrahim Ferrer
o Need Your Love so Bad – Little Willie John
o Neon Lights – Kraftwerk
o Ratts of the Capitol – Mogwai
o Sad Mood – Sam Cooke
o Scatterbrain – Radiohead
o Since I’ve Been Loving You – Led Zeppelin
o Small Black Flowers That Grow in the Sky – Manic St Preachers
o Song Cry – Jay Z
o Sour Times – Portishead
o State Trooper – Bruce Springsteen
o Stinkin’ Thinkin’ – Happy Mondays
o Strange News from Another Star – Blur
o Suicidal Thoughts – Notorious BIG
o This is Hardcore – Pulp
o Too Far Down – Hüsker Dü
o Underneath the Weeping Willow – Grandaddy
o Vicious World – Rufus Wainwright
o Visions of Johanna – Bob Dylan
o Way To Blue – Nick Drake
o Well I Wonder – Smiths
o What Becomes of the Broken Hearted – Jimmy Ruffin
o Where Did You Sleep Last Night? – Nirvana
o Where Do We Go Now But Nowhere? – Nick Cave & the Bad Seeds
o Whisky & Water – Tindersticks
o Who Knows Where the Time Goes? – Sandy Denny
o Wichita Lineman – Glen Campbell
o Wild Is the Wind – David Bowie
o Will Never Marry – Morrissey

Ultimate Downer Track: Big Louise – Scott Walker

I guess it can be interpreted different ways, but for me that's like the most depressing line ever. Have you heard the acoustic version? It makes it ten times more depressing because it doesn't have all those heavenly harps and stuff.

Martha by Tom Waits. Hands down!

After hearing that 3rd verse in the acoustic version I'm going to concede this one to you. Depressing indeed. Wonderfully underrated song, and when that line is sung it is one of the most powerful Radiohead moments.

Grapefruit Moon is pretty damn sad as well. The entire album is a really emotional experience.

Moonlight Mile by the Rolling Stones is an extremely heartfelt song and could definitely go under the depressing category, I highly recommend it. Something In The Way by Nirvana is another good one it doesn't get much sadder then that tone wise. Another lesser known one would be Cold Again by Freedy Johnston.

Check out "Wai"- by Bonnie "Prince" Billy. I don't listen too closely to lyrics till like the 800th time through but upon the first 100 listens its at the very least melancholy. And it's the most beautiful song I know right now.