Gloomy Sunday by Billie Holiday must be impossible to equal.
Hallelujah, the Jeff Buckley version
BTW, Diamanda Galas does it well, but I still think Lady Day has the most gripping version.Billie Holiday: Gloomy Sunday Her voice just tears at my heart.
She also sings “I’ve Got My Love to Keep Me Warm”, a Irving Berlin tune, and makes you feel all the loneliness in the world. She sings about having that love, and you sense that it’s like the wishful thinking of a child, and that she’s all alone, out in the cold winter, dreaming of such a love. When I listen to this song, I invariably pour myself a tumbler of scotch and dilute it with my tears.
Ben Folds’ Brick is about as sad a song as I’ve ever heard, especially when you know the background of it.
I’m sure I’m not the only one who finds “Happy Birthday” a little more depressing every year.
The eight-minute song California One/Youth and Beauty Brigade by The Decemberists is considered by many to be their best ballad. But few realize what the song is actually about. (Note: these lyrics are not the full song, just a portion of it. Full lyrics here. )It starts off with the narrator inviting the love interest of the song to take a drive with him on California One and enjoy the beauty of the surroundings:
And the road a-winding goes
From golden gate to roaring cliff-side
And the light is softly low as our hearts Become sweetly untied
Beneath the sun of California one
Later there is a chord change and the song subtly segues into a second part, with these lyrics:
*
Annabelle lies, sleeps with quiet eyes
On this sea-drift sun
What can you do?
And if I said, O it’s in your head
On this sea-drift sun
What can you do?*
It seems like this has nothing to do with the rest of the song. Who is Annabelle? And what does the bit about “it’s in your head” mean? But then the song goes in yet another direction, as the tempo slows down and a heartbeat-like bass-drum line takes over. If you listen very carefully, you can hear a female voice speak the following:
I’ve heard of ghosts…good ghosts who wander the battlefield at night, guiding soldiers out of danger. You can see them almost everywhere. [Unintelligible.] …A stray bullet…if I were such a ghost, I would stay so close to you, you could feel my breath on your cheek.
Hmm…now what does this have to do with anything?
It’s not until the final portion of the song, when he talks about the “youth and beauty brigade” that makes up part of the title, that we get a clue:
*
We’re lining up the light-loafere’d
And the bored bench warmers
Castaways and cutouts, fill it up
Come join the youth and beauty brigade
*
Knowing this, the parts of the song all come together and tell a story. There is obviously some kind of war going on. Given the information in the song, I’m going to assume that it’s some kind of civil war involving California - maybe the state has seceded from the union, or something. We can surmise that it’s set in the future. There was a call to arms, and the military needed more manpower so it had do accept anyone who could fight: young men who were accustomed to idle and passive lives (bored bench warmers) gay (light-loafered) or social outcasts (castaways and cutouts). We can assume that the narrator was one of these recruits who would not ordinarily be interested in fighting, but was coerced into it.
Presumably, he had a girlfriend back home (Anabelle,) and the cryptic line about the ghosts on the battlefield protecting the soldiers, spoken by a female voice, is supposed to represent the narrator’s conception of Anabelle as his guardian - his imagining that she is there, watching over him, when he goes into combat.
When he says, “it’s in your head,” after the first verses of the song, to me this is an indication that the scenario of driving through the California countryside with his lover, drinking wine, etc, is a hallucination, and that the narrator is actually dead, and was dead from the very beginning of the song. He was killed in battle, suffering an unceremonious death after being lured into the “youth and beauty brigade” with promises of glory. As he is dying, he’s thinking about Anabelle, about the idealized trip that he wanted to take with her on California One, and then in the final portion of the song, cynically recounting how he was lead to his death by government propaganda. Awful, just awful.
This may seem like an overinterpretation, but it makes sense when you consider the Decemberists’ obsession with war, and their many songs about historical battles from World War I to the Civil War to Iraq. It seems to me they’re trying to make a statement about how war is not glorious but tragic, and steals the lives of idealistic young men who believed the recruiting propaganda. Knowing this, the song becomes much deeper, but also more depressing.
Send In the Clowns. Sinatra did a nice version of this.
Rainy Days and Mondays. Karen Carpenter
Ol’ Man River. Paul Robeson
**Is That All There Is? ** Peggy Lee
Woods of Darney - Richard Thompson
We Could Leave Right Now - Oysterband
‘Given Time’ - Rainbow Chasers (Written by Ashley Hutchings, it’s about his meeting with Nick Drake who wasn’t given any time at all…)
‘The Reaper/My Bonny Boy/Scarecrow/Battle of the Somme’ - The Home Service. A folk-rock medley about World War One:
See the barbed wire growing like a bramble on the land
See a farm turned to a fortress, a future turned to sand
See a meadow turned to mud and from it grows a hand…
I think the most depressing song I’ve ever heard is “Down from Dover” by Dolly Parton.
Oh!! Oh!! How could I forget one that was mixed by one of my dad’s best friends?!
Pirates of the Mississippi- Feed Jake
That’s a duet with Allison Krauss and Brad Paisley.
I’d have to agree with Lucky on it, too.
Ditto with earlier posters on Lady Day’s version of Gloomy Sunday.
Others on my list:
I Can’t Make You Love Me - Bonnie Raitt
Molly Ban - The Chieftains and Allison Krauss
Diana Krall’s version of Danny Boy
There were Roses - Tommy Sands
And, frankly, despite the upbeat tune, I think the words to Born to Run are really pretty morose.
And just checking - **Willie McBride ** and The Green Fields of France have both been mentioned. I think they’re different titles for the same song. 
(Which is awfully depressing, btw)
Two I didn’t notice mentioned (though I scanned this thread rather quickly):
Red Dirt Girl - Emmylou Harris
Keep Me in Your Heart - Warren Zevon
Love, Me by Collin Raye
Alyssa Lies by Jason Michael Carroll
Someone already mentioned Whiskey Lullaby, so Hi Opal!
Concrete Angel by Martina McBride.
The 8th of November by Big & Rich
Depressed enough yet?
Good call, jjimm. I play piano in a French cabaret/music hall group, and we do Ne me quitte pas. Perhaps the saddest song ever.
Part of the lyrics, as translated by our singer:
*We’ve often seen erupting the fire of the ancient volcano
We believed to be too old
There are, I was told, burnt fields that produce more corn
Than the best April
And at dusk, for a flamboyant sky, doesn’t red
Blend perfectly with black?
Don’t leave me, don’t leave me, don’t leave me
Don’t leave me, I’ll stop crying, I’ll stop talking
I’ll hide here and watch you dancing, and smiling, and listen
To you singing and laughing. Let me become the shadow of your
Shadow, the shadow of your hand, the shadow of your dog, but
Don’t leave me, don’t leave me, don’t leave me*
(The rest of the lyrics, in English and French, here.
I don’t speak French, and think Brel is one of the greats for raw emotion.
Other songs that rate “most depressing”:
Bruce Springsteen
Racing in the Street
Atlantic City
Highway Patrolman
One Step Up
Paul Simon
American Tune
The Band
It Makes No Difference
Bill Morrissey (folk guitar/singer/songwriter)
Man From Out of Town
Casey, Illinois
Crash Test Dummies
Superman’s Song
Dire Straits
Brothers in Arms
Don Henley
A Month of Sundays
Joe Jackson
Trying to Cry
Drowning
. . . are a few others, to add to the great list we’ve got already.
I’ve only heard one of their songs and that was depressing enough for me (Have You Forgotten from the Vanilla Sky soundtrack)
Also depressing:
Walk on the Ocean - Toad the Wet Sprocket
Landslide - Fleetwood Mac (also covers by Tori Amos, Smashing Pumpkins, and Sheryl Crow)
Fair - Remy Zero
You’re Beautiful - James Blunt
Fade into You - Mazzy Star
Nothingman - Pearl Jam
Nobody Home - Pink Floyd
My Friends - Dar Williams
Independence Day - Ani DiFranco
If I Lived Right - Tracy Chapman
I Just Don’t Think I’ll Ever Get Over You and Waiting For My Real Life to Begin - Colin Hay
“Full of Grace” – Sarah McLachlan
Lyrics sample:
The winter here’s cold, and bitter
It’s chilled us to the bone
We haven’t seen the sun for weeks
Too long, too far from home
I feel just like I’m sinking
And I claw for solid ground
I’m pulled down by the undertow
I never thought I could feel so low
Oh, darkness, I feel like letting go
Ugh. Always makes me want to crawl into bed and stick my head under the covers and cry.
“Emyli” – Pretty Balanced
emyli everybody wants to be you
they don’t know the shit that you’ve been through
they just like the way you look
the way you dress
the way you walk
they couldn’t care less about the way you took a beating
Nothing like a song about domestic abuse and covering it up to be a real downer. But it’s still a great song. Actually, come to think of it, a lot of Pretty Balanced songs are mega-depressing. Take Mel and Colin or Spring Cleaning.
Wow, can’t believe no one’s mentioned Tears for Fears “The Hurting”. With wonderfully uplifting vignettes such as these you can’t go wrong:
Mad World
Memories Fade
Suffer the Children
Watch Me Bleed
Start of the Breakdown
Good stuff!
Lots of songs by the Smiths and Morrissey, particularly “Every day is like Sunday” and “There is a light that never goes out.”
No Tom Waits yet? I can’t listen to “Invitation to the Blues” or “San Deigo Serenade” without several shots of whiskey and a hanky.
Not to mention the original by Bobbie Gentry