Forgot... Shannon by Henry Gross (about a dog swimming away)

I love dogs

/Maybe she'll find an island, with a shady tree... *sniff*

Natalie Merchant - "My Beloved Wife"
Warren Zevon - "Keep Me In Your Heart"
Joey Ramone - "Don't Worry About Me"
Connie Francis - "I Will Wait For You"

What about "Mad World" - the Gary Jules version?

And, I can't listen to "When She Loved Me" by Sarah McLaughlin, from the Toy Story II soundtrack. If I watch the movie, I always turn into a blubbering mess right there.

Boulderdash: Warren Zevon - "Keep Me In Your Heart"

After seeing his last performance on Letterman, everything Warren Zevon sang makes me a little verklempt.

I'm going to go ahead and add Jeff Buckley's version of "Hallelujah."

Alone Again Naturally - Gilbert O'Sullivan.

Hender: I'm going to go ahead and add Jeff Buckley's version of "Hallelujah."

I agree. Absolutely beautiful. I played it for my mom when we drove down to FL last month. I just said to not speak for the 7 some odd minutes, just listen to the man and the music. Powerful song.

She ran calling "Wildfire!" - Michael Martin Murphy

Sir Cumference the Flatulent: Alone Again Naturally - Gilbert O'Sullivan.

It's a completely worthless list without that song.

Hender: I'm going to go ahead and add Jeff Buckley's version of "Hallelujah."

Nice, but I find Cohen's much more powerful. Besides, he thought of it.

For lyrical despair, off the top of my head, Radiohead's "Fake Plastic Trees" is on the top of my list. Talk about loneliness. Sinatra's entire album "In the Wee Small Hours" would drive any of these emo kids right over the edge. This, THIS is how you express loss and angst.

"Holes in the Floor of Heaven" gets me every time. That and I Pagliacci.

/Like a baby

Boulderdash: Warren Zevon - "Keep Me In Your Heart"

Seriously, how could you not have a song from an album a man wrote about his own slow descent into cancer-infused death because he didn't feel like going to the doctor?

I'd also like to take off the U2 reference, since nothign by Bono is anything besides pretentiously awful and add:

Dismemberment Plan - "What Do You Want Me to Say?" or "Face of the Earth"
Wilco - At Least That's What You Said
Ween - Fluffy
Grand Funk - Mean Mistreater

Maybe it's just me, but "February Stars" by Foo Fighters gets to me. I thought it was great on The Colour And Shape, but when Skin and Bones came out, it really hit home.

How to Disappear Completely by Radiohead

Nabb1: Hender: I'm going to go ahead and add Jeff Buckley's version of "Hallelujah."

Nice, but I find Cohen's much more powerful. Besides, he thought of it.

I see Leonard Cohen vs. Jeff Buckley signing "Hallelujah" sort of the same way as I see NIN vs. Johnny Cash with "Hurt": one wrote it and first performed it, the other perfected it.

Cohen's gravely voice just doesn't work for me on that song. It seems out of character for the lyrics. I feel the same way about Gary Jules's version of "Mad World," because even though I like Tears for Fears they just couldn't nail the sentiment of the song.

Also:

Built to Spill - The Weather
My Morning Jacket - Knot Comes Loose/Dondante
Flaming Lips - Feeling Yourself Disintegrate

Stephen Malkmus - Church on White
That Sigur Ros song at the end of Life Aquatic
Amazing Grace on Bagpipes
.38 Special - Hold on Loosely (brings me to tears every time)

"All by myself" didn't make the list?

I can't think of a sadder, more hopeless tune.

Hender: I see Leonard Cohen vs. Jeff Buckley signing "Hallelujah" sort of the same way as I see NIN vs. Johnny Cash with "Hurt": one wrote it and first performed it, the other perfected it.

Cohen's gravely voice just doesn't work for me on that song. It seems out of character for the lyrics. I feel the same way about Gary Jules's version of "Mad World," because even though I like Tears for Fears they just couldn't nail the sentiment of the song.

I agree with you on "Mad World," but I have the opposite view on "Hallelujah." I think Cohen's version, with the chorus and the sweeping sort of hymnal feel to it plays off nicely compared to the lyrics, creating a bit of a poignant contrast. Buckley just went for the obvious, albeit in a very nice way. I can't say Buckley brought any innovation to the table. Gary Jules took a mediocre Tears for Fears song and gave it a new life. (Okay, maybe it's better than mediocre, but it was hardly memorable.)

Jeff Buckley's Hallelujah is heartbreaking, but only when you've got the emotional connection and the time. When you have that, you sit there and participate in the sadness he's conjuring up for you. When you don't, you sit there and think, "Man, this is self-absorbed"

Nabb1: Buckley just went for the obvious, albeit in a very nice way. I can't say Buckley brought any innovation to the table. Gary Jules took a mediocre Tears for Fears song and gave it a new life. (Okay, maybe it's better than mediocre, but it was hardly memorable.)

1) I considered Buckley as a pretentious hack for doing that. It's like playing Taps on a trumpet instead of a bugle.
2) How much would that Gary Jules song have an impression without Donnie Darko? I think it's sad, but it's saditude is heightened by its incorporation with the movie's sad montage.

Great, in two hours, a liter is going to come in here and say "Sunday Bloody Sunday"

El Chode: Stephen Malkmus - Church on White

That's a good call right there, especially knowing the back story.

You could have also said Flaming Lips "Waitin' On A Superman."

Solid State Vittles: You could have also said Flaming Lips "Waitin' On A Superman."

I could, and I almost did, but I think the beauty of Feeling Yourself is that it's got like 12 words in it total, and the prapprapprapprappaprapprap part somehow adds to it all.

I also wanted to say "I Heard You Looking" by Yo La Tengo, but that's more because it was once played during a sad situation and it fit, but isn't necessarily sad.

Nabb1: Hender: I see Leonard Cohen vs. Jeff Buckley signing "Hallelujah" sort of the same way as I see NIN vs. Johnny Cash with "Hurt": one wrote it and first performed it, the other perfected it.

Cohen's gravely voice just doesn't work for me on that song. It seems out of character for the lyrics. I feel the same way about Gary Jules's version of "Mad World," because even though I like Tears for Fears they just couldn't nail the sentiment of the song.

I agree with you on "Mad World," but I have the opposite view on "Hallelujah." I think Cohen's version, with the chorus and the sweeping sort of hymnal feel to it plays off nicely compared to the lyrics, creating a bit of a poignant contrast. Buckley just went for the obvious, albeit in a very nice way. I can't say Buckley brought any innovation to the table. Gary Jules took a mediocre Tears for Fears song and gave it a new life. (Okay, maybe it's better than mediocre, but it was hardly memorable.)

Am I the only person who thinks the best version of Hallelujah is Rufus Wainwright? I love it.

My vote is for "Kathy's Song". Sung by Garfunkel is it a wonderful love song, and sung by Eva Cassidy it is hauntingly heartbreaking.

No room for hip hop on the list? "All That I Got Is You" by Ghostface Killah

Check it, fifteen of us in a three bedroom apartment
Roaches everywhere, cousins and aunts was there
Four in the bed, two at the foot, two at the head
I didn't like to sleep with Jon-Jon he peed the bed
Seven o'clock, pluckin roaches out the cereal box
Some shared the same spoon, watchin saturday cartoons
Sugar water was our thing, every meal was no thrill
In the summer, free lunch held us down like steel
And there was days I had to go to Tex house with a note
Stating "Gloria can I borrow some food I'm dead broke"
So embarrasin I couldn't stand to knock on they door
My friends might be laughin, I spent stamps in stores
Mommy where's the toilet paper, use the newspaper
Look Ms. Rose gave us a couch, she's the neighbor
Things was deep, my whole youth was sharper than cleats
Two brothers with muscular dystrophy, it killed me
But I remember this, mom's would lick her finger tips
To wipe the cold out my eye before school wit her spit
Case worker had her runnin back to face to face
I caught a case, housin tried to throw us out of our place
Sometimes I look up at the stars and analyze the sky
And ask myself was I meant to be here... why?

Or maybe "Ghetto Bastard" from Naughty by Nature

El Chode: 2) How much would that Gary Jules song have an impression without Donnie Darko? I think it's sad, but it's saditude is heightened by its incorporation with the movie's sad montage.

It was used in a movie? I thought it was just in Gears of War ads.

/*sniff*
//those poor Locust Horde

You Are My Sunshine

Solid State Vittles: El Chode: Stephen Malkmus - Church on White

That's a good call right there, especially knowing the back story.

What's the back story? Always enjoyed this song.

Danny Callahan

Hender: It was used in a movie? I thought it was just in Gears of War ads.

/*sniff*
//those poor Locust Horde


Yeah, it actually fit really really well because it shows Patrick Swayze all upset about getting the cancer (new window)

El Chode: Hender: It was used in a movie? I thought it was just in Gears of War ads.

/*sniff*
//those poor Locust Horde


Yeah, it actually fit really really well because it shows Patrick Swayze all upset about getting the cancer (new window)

Sarcasm, man. Adjust your radar!

No smiths means it's wrong.

I'll also add:

Scud Mountain Boys "A Ride"
Pernice Brothers "Chicken Wire" (same dude from Scud Mtn. Boys, that is one sad dude)
Tom Waits "Grapefruit Moon"
Tom Waits "Hang Down Your Head"
Acetone "Things Are Gonna Be Alright" (singer actually killing himself adds a cruel sense of irony to this one)
Beach Boys "I Just Wasn't Made For These Times"
Uncle Tupelo "Still Be Around"
Replacements "Answering Machine"

I liked the inclusion of Elliott Smith's "Between the Bars" just because I saw him out at bars pretty much every night my last month living in Portland, almost always by himself. He invited me over for a toast the last night. Cheers *clink*.

Heartbreaking songs about heartbreak:

Meat Loaf:

Is Nothing Sacred
Man of Steel

dammit..have to make a phone call.

Hender: Sarcasm, man. Adjust your radar!

Sorry, it's a music thread. Serious business.

El Chode: Hender: Sarcasm, man. Adjust your radar!

Sorry, it's a music thread. Serious business.

The fight against the Horde is serious business.

SmashLimousines: Solid State Vittles: El Chode: Stephen Malkmus - Church on White

That's a good call right there, especially knowing the back story.

What's the back story? Always enjoyed this song.

His buddy was an up and coming writer in New York that OD'd. This was his goodbye.

yeah... everybody hurts came out right when i was a vulnerable, hormoned teenager so every time i hear that song, it's not only depressing as hell, but it reminds me of how awful and depressing being a teenager was, so it's a double whammy.

sigh.

While I do agree with Boulderdash: Warren Zevon - "Keep Me In Your Heart", I'd also add:

Love Song for a Vampire - Annie Lennox
Getting to the Point - ELO
Redemption Song - Joe Strummer (see above argument about originals vs. covers)
Mindy Smith - One Moment More (I think this is the winner)
Bangles - Something to Believe in

oh, and most of the songs lucinda williams has ever written, including most of the album "car wheels on a gravel road". brilliant album, but so, so sad.

Also, a Sufjan song and not Casimir Pulaski Day?fark that noise.

Oh, wait, I forgot the best one:

I Will Love You - Fisher (new window)

Wow, I hadn't heard the "original internet hit" in a while. Damn.

Tatsuma: No smiths means it's wrong.

Yep.

Good list, I can't really argue, but for those of us who have been there, "The Whiskey Ain't Working Anymore" deserves honorable mention.

There was a time, I could drink my cares away,
And drown out all of the heartaches,
That hurt me night and day.
When the thought of you came crashing through,
I'd have one more.
But now the whiskey ain't workin' anymore.

Solid State Vittles: His buddy was an up and coming writer in New York that OD'd. This was his goodbye.

Similar Story behind "Dondante" (new window)

Demons and Wizards - Fiddler on the Green (new window)

One of the most beautiful songs ever written.

I agree with many of the comments, but the list also needs some Townes Van Zandt.

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... Tecumsah valley

The name she gave was Caroline
daughter of a miner
her ways were free
it seemed to me
that sunshine walked beside her

Hender: I'm going to go ahead and add Jeff Buckley's version of "Hallelujah."

I've always preferred Cale's version, personally.