I have a few options for most depressing, and obviously each for different reasons:

This song is completely ethereal, yet so hopeless at the same time. I always imagine this song illustrating a story of attempting to save someone that you simply cannot:

Sigur Ros' "Saeglopur"

Once you've fully listened to and fathomed these lyrics, there isn't many things more depressing than a song about not only losing a child, but blaming yourself for it. So relevant:

Modest Mouse's "3rd Planet"

And after a pretty dark (ah, teenage angst) period in my life, this song is always what I resorted to playing alongside downing a bottle of wine:

Explosions in The Sky's "What do you go home to?"

Sorry, I cannot post links quite yet seeings that I am a new user. But I swear, each song hits you in some fashion.

^Definitely good choices! 3rd Planet is super depressing and I really like how they pair super dark lyrics with such upbeat happy sounding music. Seaglopur is also really sad sounding, but I think that Gong is way more depressing :3
And I actually don't think I've ever heard What Do You Go Home To, surprisingly. What album is it on?

Personally, this is one of the most depressing songs I've ever heard:

It's on the album, "Suddenly I miss everyone" which is my second favorite album of theirs :)

Jason Molina - It's Easier Now


Songs:ohia - Trouble Will Find You

A lot of his songs could go here really, most of it's quite bleak and sparse. I don't think there are many musicians who can do so much with so little. I'm so gutted he died.

Nico - Eulogy to Lenny Bruce

This song creeps me out a bit. Life just seems a bit hopeless whenever I listen to it. Good song though.

Pink Floyd - Time gets more depressing every passing year.

There are others like Smashing Pumpkins - Wound and The Everlasting Gaze that I find hard to listen to but that's more down to personal associations rather than the music itself.

"Lost Cause" by Beck.


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It was on Vevo if I remember well...

''The saddest song in the world''
Artist not remembered

Post \3/

This is the saddest song...The song is the singer's story about losing his dog in the Georgia Strait ( The strait between Vancouver Island, and the mainland (Vancouver) )

Sings it as if it were about a woman sort of, but its a true story about his pooch.

Gone Away - The Offspring
Cough Syrup - Young the Giant
Only Time - Enya
The Unforgiving - Metallica