Black Crowes - Cursed Diamond, Descending
Jeff Buckley - Last Goodbye
Wilco - Misunderstood
Ben Harper - Walk away, Another Lonely day, Alone, the drugs don’t work (cover)
As the 27-year-old child of a divorce that took place 22 years ago, this song brings tears to my eyes to this day.
What’s-his-name hit the nail on the head when he wrote this song.
stv
Janis Joplin: Me and Bobby McGee.
I don’t think of Nightswimming as sad. Nightswimming makes me think of good times spent with friends.
The first song that ever really got to me was “The Only One” by Huey Lewis. It’s about this guy who gets hit by a car.
I would also like to nominate “Evaporated” by Ben Folds Five. Here’s the best line:
“I poured my heart out…it evaporated.”
Think of the ending to Ol’ Man River :
I gits weary and sick of tryin’;
I’m tired of livin’ and scared of dyin’
And Ol’ man river, he just keeps rollin’ along
The utter hopelessness of it. So very sad.
surprised not to see more tori amos here.
my votes are for her:
“Northern Lad”
and
“1000 Oceans” (Especially at time like now when my fiancee, who hooked me on Tori, is an ocean away)
Both of Steve Earle’s death penalty songs - “Billy Austin” and “Ellis Unit One” are very sad. They’re very good, but very sad.
“Neither One of Us (Wants To Be the First to Say Good-bye)” by Gladys Knight and the Pips is a heartbreaking “the relationship is over and I don’t want to admit it and I don’t want to hurt you, either” song.
Comedian Richard Jeni used to tell a story about using “The Wreck of the Edmund Fitzgerald” to clear his house when a party was over. The lyrics are so depressing that people would find excuses to leave. 
Two for me: (forgive me if these have already been nominated)
God, John Lennon
That's the Way It Should Be, Led Zeppelin
Both choke me up every time.
-j
Well, the old man is still sad about it. The lines preceding my previously quoted verse are:
I read those words just hours before my Grandma passed away,
In the doorway of a church where me and Grandpa stopped to pray.
I know I’d never seen him cry in all my fifteen years;
But as he said these words to her, his eyes filled up with tears.
sniff
Two quick ones:
A late recording of Hank Williams doing “I Can’t Escape From You.” It was done a few months before he drugged himself to death, and it’s just him and an acoustic guitar. You can hear the terrible sadness and weariness in his voice, and at one point his voice sort of catches in the middle of the chorus, and you can tell his heart was broken.
Little Rain (For Clyde) - Tom Waits
She was fifteen years old,
and she’d never seen the ocean.
She climbed into a van
with a vagabond
And the last thing she said
was, “I love you, mom.”
And a little rain never hurt no one.
Two artists already named but I don’t think these songs were mentioned yet:
“Fake Plastic Trees” by Radiohead
“Lover You Should Have Come Over” by Jeff Buckley
And “Sadly Beautiful” by the Replacements
Oo oo ooh, katey. You reminded me…
“Satisfied Mind,” by Jeff Buckley (yes yes, I know it was originally by Porter Wagonner, so all you musicologists jest calm down.)
The lyrics are just so terribly appropriate, since he died so young. It was, in fact, played at his funeral. Plus I’ve never heard his voice more glorious than on that song.
Miles Davis “Blue In Green” - The piano at the end of the song is truly haunting. The rest of the album that this tune is on, Kind of Blue, is a fantastic downer.
I would like to nominate another Jeff Buckley cover as well, this time a Leonard Cohen original: "Hallelujah"
well, maybe there’s a god above
but all i’ve ever learned from love
was how to shoot somebody who outdrew you
it’s not a cry that you hear at night
it’s not somebody who’s seen the light
it’s a cold and it’s a broken hallelujah
To hear Buckley sing it takes my breath away every time.
Here area a few of mine:
Trisha Yearwood’s “Like We Never Had a Broken Heart” – two people making love just because they have no one else (co-written by Garth Brooks, FYI). It’s the “don’t be afraid to close your eyes” line that gets me.
Let’s make love tonight…
Like we never had a broken heart…
Don’t be afraid to close your eyes…
Pretend I’m someone that you love…
And I won’t have to tell you lies…
‘Cause it’s not you I’m thinkin’ of…
Townes Van Zandt’s “Tecumseh Valley” (especially as performed by Nanci Griffith and Arlo Guthrie). It tells the story of a miner’s daughter who was sent to town for the winter.
She saved enough to get back home
when spring replaced the winter
but her dreams were denied
her pa had died
the word come down from Spencer
So she turned to whorin’ out on the streets
with all the lust inside her
and it was many a man
returned again
to lay himself beside her
They found her down beneath the stairs
that led to Gypsy Sally’s
in her hand when she died
was a note that cried
fare thee well… Tecumseh valley
Allison Moorer’s album “The Hardest Part” has a hidden track called “Cold, Cold Earth.” It’s sad by itself, but it’s heartbreaking when you realize she’s singing about the murder-suicide of her parents:
A slave to the bottle
He’d driven his family to leave
A wife and two daughters
He treated so terribly
He went into the city
To try to make amends
Asked his love for pity
But she would not give in
Overwhelmed with sadness
He reached for his gun
And took her life along with his
Before the morning sun
Then there’s John Lennon’s “Mother.” I was going to quote the lyrics when I realized it was the absolutely depths-of-his-soul screams that make the song so tragic.
Dave Matthews Band (don’t hurt me!)- Pay for What you Get
Tori Amos - China
Tori Amos(this is a remake) - '97 Bonnie & Clyde
Deep Forest - The First Twilight
Pizzicato 5 - Sweet Thursday
I’ve got a huge case of depressing CDs, and yet I can’t think of sad songs.
The two songs that stick out to me off the top of my head are Leader of the Band by Dan Fogelberg (strong personal feelings) and I also think Fields of Gold by Eva Cassidy is pretty damn sad, sadder than Sting’s version.
And as a baseball junky forceably retired from the game, This Used to be My Playground by Madonna.
Without a doubt;
ALONE AGAIN NATURALLY (Gilbert OSullivan) This song came out when I was in first grade. I can remember hearing it on the car radio and I would just curl up on the floor of the car in the fetal postion and practically have an anxiety attack! At the age of 5 or 6! This is not exaggeration.
DOWNBOUND TRAIN (Bruce Springsteen)
ONE STEP UP & TWO STEPS BACK (Bruce Springsteen)
One just needs to listen to the lyrics of the Springsteen songs to understand why.
Both “She’s Leaving Home” and “Wharf Rat” are positive songs in my book.
“She’s Leaving Home” is about a woman who’s been living a stifling, oppressive life and leaves home. The last stanza contains the line “She…is having…fun.” She meets a guy from the motor trade, has a date. Her life is completely transformed.
As far as Wharf Rat goes, August West may be a old man asking for spare change for a cup of coffee, but he’s got his spirit left. “I’ll get up and fly away…I’ll get up and fly away…fly away.”
<Cue Brent’s big Hammond B-3 intro followed by a searing Jerry solo>
I can’t believe no one has mentioned How Soon Is Now by the Smiths. This is by far the saddest song ever.
I used to think that At Seventeen by Janis Ian was really sad, until I understood the lyrics. It’s totally an in-your-face revenge song.
Sample lyrics:
Hah! And when I was a kid, Wildfire always made me cry. That poor horse!