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Posted at 10:43 AM ET, 12/15/2006

Friday List: Sad Songs

By Liz Kelly

Sad songs. They say so much. (Or so sang Elton John in his mid-80's paean to the sappier side of the musical spectrum.) And obviously others agree. A new "scientific" study has named The Verve's "The Drugs Don't Work" as the saddest rock/pop song ever. Here's the full Brit-centric list:

1. The Verve - "The Drugs Don't Work"
2. Robbie Williams - "Angels"
3. Elton John - "Sorry Seems To Be The Hardest Word"
4. Whitney Houston - "I Will Always Love You"
5. Sinead O'Connor - "Nothing Compares 2 U"
6. Will Young - "Leave Right Now"
7. Elvis Presley - "Are You Lonesome Tonight?"
8. Christina Aguilera - "Beautiful"
9. James Blunt - "Goodbye My Lover"
10. Radiohead - "Fake Plastic Trees"

I dunno about the above list, but I think Sir Elton has a point.

There seems to be a sad song for every emotional let down the world throws at me us. Well do I remember working myself into a frenzy over repeated childhood listenings of Michael Martin Murphey's "Wildfire" (hush you Weingarten chatters) and I will never forget the roommate who literally paused my emotional breakdown to cue up the Eagles' "Wasted Time" when my college boyfriend abruptly dumped me. And, being a good Irish girl, I can't help but tear up if I even hear a musak version of "Danny Boy." Then, of course, there's The Pretenders' "Back on the Chain Gang" and "I Go to Sleep." Still, for me, the Velvet Underground has a pretty big portion of my sad songs playlist covered -- "I'll Be Your Mirror," "All Tomorrow's Parties," "Stephanie Says." Lou knows from sad.

What songs make your eyes go all misty or get you in a wistful mood? Add your picks to the comments section.

By Liz Kelly  | December 15, 2006; 10:43 AM ET
Categories:  Friday Lists  
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I was in high school and college in the '80s, but I still have sad, sad memories of that '70s song from Brian's Song, "The Hands of Time" maybe?

For the '80s, how about "Into the Mystic" by Van Morrison or?

Posted by: Kelli | December 15, 2006 10:57 AM | Report abuse

When I'm sad I just play the following playlist on repeat (eat eat popeyes):

Jewel - Foolish Games
Radiohead - How to disappear completely
Fiona Apple - Love Ridden
Nine Inch Nails - Hurt
Tori Amos - Precious Things
Beth Orton - Blood Red River
Portishead - Roads
Morcheeba - Over and Over
Moby - Why does my heart feel so bad

Haha I swear I'm not a cutter!

Posted by: not bluto | December 15, 2006 10:57 AM | Report abuse

Oh wait, I forgot She's like the Wind, by Patrick Swayze

Posted by: not bluto | December 15, 2006 10:58 AM | Report abuse

When my college boyfriend dumped me -- for another girl -- I played Fleetwood Mac's "Landslide" over and over and over. And then about a month later, the Dixie Chicks version came out. I can't hear that song now without a feeling of empowerment coming over me.

"Well, Ive been afraid of changing/cause Ive built my life around you/But time makes you bolder/Children get older/Im getting older too"

Posted by: Anonymous | December 15, 2006 11:01 AM | Report abuse

Not just one song but the entire album Bitter by Me'Shell NdegeOcello. Love her, love her music but that cd gets me every time I play it. Special note: "Wasted time" and "Fool of me". Those songs won't make you wanna get up and dance, just wallow for a bit and they're addictive.

Posted by: petal | December 15, 2006 11:05 AM | Report abuse

'When It's Cold I'd Like to Die' by Moby

Posted by: koffee | December 15, 2006 11:05 AM | Report abuse

Karma Police and Creep are also really depressing, but How to Disappear Completely makes me feel like gouging my eyes out with a melonballer is fun:

In a little while
I'll be gone
The moment's already passed
Yeah, it's gone

I'm not here
This isn't happening
I'm not here, I'm not here

Posted by: not bluto | December 15, 2006 11:08 AM | Report abuse

Theme song from Ice Castles
Garth Brooks' The Dance
Elton John's tribute to Diana (England's Rose or something along that line)

For the holidays:
Christmas Shoes

Posted by: WDC | December 15, 2006 11:08 AM | Report abuse

The Allman Borthers "Tied to the Whipping Post". It's not just sad, it's MISERABLE. "Good Lord I feel like I'm dying..." (I was very meodramatic in college and played it whenever I'd been disappointed. Woe is me!)

Posted by: KiKi | December 15, 2006 11:10 AM | Report abuse

I'm completely with you on the Velvet Underground. I could even through in a few more: "Afterhours," "New Age," and "Oh Sweet Nothing." But the two most devastating songs I've ever heard are "Holocaust" by Big Star and "The Kids" by Lou Reed. And oh, how could I forget "Scratches on the Door" by Freakwater.

Posted by: Mr Ecks | December 15, 2006 11:12 AM | Report abuse

I'd go with Johnny Cash's cover of Hurt. Very poignant, particularly given the circumstances around its recording.

Posted by: derberg | December 15, 2006 11:13 AM | Report abuse

"Tell Me There's A Heaven" by Chris Rhea makes me want to curl up in a ball and melt.

Posted by: CMC | December 15, 2006 11:17 AM | Report abuse

"Lazarus" by Porcupine Tree off of "Deadwing".

"Moonlight is bleeing from out of you soul" still tears me up.

Posted by: scott | December 15, 2006 11:19 AM | Report abuse

I once had to leave a grocery store after bursting into tears.

They were playing "Cats In The Cradle".

Posted by: sb | December 15, 2006 11:22 AM | Report abuse

When I was in college and my boyfriend dumped me(this list should had been called "Sad Songs for when you dumped in college"), "Crazy for You" by Madonna always made me cry.

Posted by: Lisa | December 15, 2006 11:22 AM | Report abuse

Tori Amos makes me sad.

And I always thought Eric Clapton's Tears in Heaven was sad, but I heard it once after my son was born and weeped.

Posted by: mfd | December 15, 2006 11:23 AM | Report abuse

I'm with derberg and the Johnny Cash version of "Hurt."

Also Sheena Easton's "In the Winter," that's the one I always listen to when I'm depressed and think "man, I guess someone still has it worse than me!"

Posted by: AG | December 15, 2006 11:27 AM | Report abuse

I have no idea who sings this song, but it always makes me cry (and if you know who it is, please let me know).

It's a cover of Somewhere Over the Rainbow on a Ukele. I think it's been in a ton of movies and commercials (Meet Joe Black. I think the Rice Crispie Treats Commercial right now)

Posted by: mfd II | December 15, 2006 11:27 AM | Report abuse

"Fire and Rain" by James Taylor. Sweet and oh so sad...

Posted by: JT for sure | December 15, 2006 11:30 AM | Report abuse

Seasons in the Sun (because it was my little sister's favorite song; she died of leukemia when she was 5 years old)

Nowhere to Stand by kd lang (about child abuse)

4 and 20 by Crosby, Stills, Nash and Young

Posted by: CJB | December 15, 2006 11:34 AM | Report abuse

Eleanor Rigny by the Beatles gets me every time.

Posted by: HEC | December 15, 2006 11:35 AM | Report abuse

The Smiths, need I say more and that song the Highlander tv series always played "Dust in the wind"

Posted by: petal | December 15, 2006 11:35 AM | Report abuse

Fleetwood Mac, "Songbird"

It's kind of wistful and nice - she wants him to be happy - until you realize, she's completely giving him up and letting him go because she thinks that's best for him, even though she still wants him more than anything.

Carole King, "You've Got A Friend"
The Beatles, "For No One"
The Beatles, "In My Life"
Elton John, "Daniel"

And some that are personally depressing because I associate them with particular girls who are no longer in my life:
The Beach Boys, "Wouldn't It Be Nice"
Crosby, Stills, and Nash, "Suite: Judy Blue Eyes"

Posted by: aelfric | December 15, 2006 11:35 AM | Report abuse

my favorite breakup song was always "via chicago" by wilco. 'i dreamed about killing you again last night and it felt all right to me', you can't really beat that for passive agressive hatred

Posted by: sweetdee | December 15, 2006 11:38 AM | Report abuse

Anyone ever heard of Sarah McLachlan? Everything, absolutely everything that woman every sang was sad, so sad. Can't have a sad song list without Sarah. It's a rule. Look it up.

Posted by: Duh | December 15, 2006 11:39 AM | Report abuse

Y'all are in my wheelhouse now.

Lucinda Williams, Lake Charles. The chorus haunts me like a host of banshees.
"Did an angel whisper in your ear? Hold you close, and take away your fears, in those long, last moments."

Having lost several loved ones to cancer, I can tell you those words capture the prayers of all of us left behind.

Patti Griffin: Makin' Pies; Useless Desires; Florida.

Lou Reed: Heroin

The Smiths (I know, anything from Morrissey constitutes cherrypicking).
There Is a Light that Never Goes Out, and of course the obligatory Last Night I Dreamed Somebody Loved Me.

Bob Dylan: Simple Twist of Fate.

The Band: Acadian Driftwood.

Bruce Springsteen: Stolen Car.

Lastly, I wasn't asked but given the season I'll put forth the greatest Xmas song ever written. The Pogues, A Fairytale of New York.

Posted by: Mikey T | December 15, 2006 11:40 AM | Report abuse

Just about anything by George Jones

Posted by: singinthblues | December 15, 2006 11:41 AM | Report abuse

Tracy Chapman--Fast Car
Beth Hart--L.A. Song
Bonnie Raitt--Have a Heart
Indigo Girls--Blood & Fire
DITTO James Blunt--Goodbye My Lover
Johnny Cash--Hurt
Mariah Carey--My All
REM--Everybody Hurts

Posted by: Melanie | December 15, 2006 11:41 AM | Report abuse

Maybe it's a different kind of sad, but I choke up every time I hear it, especially these days:

Eric Bogle's "And the Band Played Waltzing Matilda," performed by the Pogues.

Then a big Turkish shell knocked me arse over tit
And when I woke up in my hospital bed
And saw what it had done, I wished I was dead
Never knew there were worse things than dying
For no more I'll go waltzing Matilda
All around the green bush far and near
For to hump tent and pegs, a man needs two legs
No more waltzing Matilda for me

So they collected the cripples, the wounded, the maimed
And they shipped us back home to Australia
The armless, the legless, the blind, the insane
Those proud wounded heroes of Suvla
And as our ship pulled into Circular Quay
I looked at the place where me legs used to be
And thank Christ there was nobody waiting for me
To grieve and to mourn and to pity
And the band played Waltzing Matilda
As they carried us down the gangway
But nobody cheered, they just stood and stared
Then turned all their faces away

And now every April I sit on my porch
And I watch the parade pass before me
And I watch my old comrades, how proudly they march
Reliving old dreams of past glory
And the old men march slowly, all bent, stiff and sore
The forgotten heroes from a forgotten war
And the young people ask, "What are they marching for?"
And I ask myself the same question.

Posted by: halleck23 | December 15, 2006 11:44 AM | Report abuse

Wasted Time -The Eagles definitely
I Take You with me - Melissa Etheridge-she has a lot of them
That's why they call it the blues- Elton John
Looking through the eyes love - Theme from Ice Castles
Leaving on a Jet Plane and Puff the Magic Dragon- Peter Paul and Mary
Thinder Road - Bruce Springsteen

Posted by: Paula | December 15, 2006 11:44 AM | Report abuse

Tom Waits - Broken Bicycles/Empty Pockets (among countless others)
Rockpile - Crying In the Rain
Ray Charles - What'll I Do?
Ella Fitzgerald - Angel Eyes (just murder, I tell you)
Rebekah del Rio - Llourando (Orbison's Crying sung acapella and in spanish)
Doc Watson - The Last Thing On My Mind

Oh I need to just stop.

Posted by: spike | December 15, 2006 11:47 AM | Report abuse

mfd II-- The Hawaiian-style Over the Rainbow/What a Wonderful World is by Israel Kamakawiwo'ole. It's on his album "Facing Future" and is probably available on other compilations/soundtracks as well...

Posted by: halleck23 | December 15, 2006 11:48 AM | Report abuse

Lou Reed, What's Good.

Posted by: Rabid Rabbit | December 15, 2006 11:49 AM | Report abuse

Beck- Lost Cause.
Gets me every time.

And apparently, as a small child, I cried my eyes out to Stan Rogers' Northwest Passage.

ukulele version of Somewhere over the Rainbow is by Israel Kamakawiwo'ole. It's beautiful.

Posted by: J | December 15, 2006 11:50 AM | Report abuse

Gilbert O'Sullivan: Alone Again Naturally
Don Mclean: American Pie
Red Hot Chili Peppers: Under the Bridge
Queen: Who Wants to Live Forever
Squeeze: Tempted

Posted by: J | December 15, 2006 11:53 AM | Report abuse

I'm with duh -- in college we nicknamed Sarah Mclaughlin CD's "sucide music volume 1, 2, 3, etc..." kind of sick, but true -- if you listen to her music when you really are sad it makes it worse -- if you're happy she's sort of calming...

Posted by: pkc | December 15, 2006 11:53 AM | Report abuse

Dido's "Here With Me" is definitely the song that makes me want to crawl into bed and just cry. Pearl Jam's version of "Last Kiss", Tim McGraw's "Don't Take the Girl" and Billy Joel's "Allentown" (I know, random) are situation songs that just make you feel so bad for the people involved.

Posted by: Melinda | December 15, 2006 11:54 AM | Report abuse

Carole King - It's too late baby , now it's too late , though we really did try to make it . Somthing inside has died , I can't hide and I just can't fake it . Ouch , hurts every time .

Posted by: shore | December 15, 2006 11:55 AM | Report abuse

Can we do 'Happy Songs' on Monday?

Posted by: dvictor | December 15, 2006 11:57 AM | Report abuse

I agree with The Verve's "The Drugs Don't Work," and J, Beck's "Lost Cause" also gets me every time.

I would add, even though it's been overplayed (on radio AND every single tv show with a doctor), the Fray's "How to Save a Life."

George Michael's "Heal the Pain"
Ben Fold Five "Alice Childress"
Pet Shop Boys "Being Boring"

Posted by: Northerner | December 15, 2006 11:58 AM | Report abuse

Wicked Game, Chris Isaak
Angie, Rolling Stones

Posted by: Jo | December 15, 2006 11:59 AM | Report abuse

I happen to be in a super sad situation this holiday season -- just found out my husband of less than a year has been having an affair -- SooOoo, I have a whole iPod soundtrack from the mess. For your wallowing pleasure:

Roger Miller -- One Dyin' and a Burying
Kirsty Maccoll -- Wrong Again
Aretha Franklin (the undisputed GREAT whenever life sucks) -- Sit Down and Cry -- actually just play a lot of early Aretha.
Nina Simone -- Ain't No Use
The Be Good Tanyas -- Waiting Round to Die
John Lee Hooker -- Serves You Right to Suffer
Tracy Nelson -- God Will
John Prine -- Speed of the Sound of Lonliness

Posted by: squiff | December 15, 2006 11:59 AM | Report abuse

I meant Ben FoldS Five.

And seeing Dido reminded me-"See the Sun" is such a sad song.

Posted by: Northerner | December 15, 2006 12:02 PM | Report abuse

Forgot to add, the British master of the sad song -- Richard Thompson

The Great Valerio
Waltzings for Dreamers (and Losers in Love)
Al Bowlly's in Heaven
Withered and Died
Down Where the Drunkards Roll

and many other brilliant and bleak

Posted by: squiff | December 15, 2006 12:03 PM | Report abuse

Ditto on The Pretenders' Back on The Chain Gang.
Other saddies:

Least Complicated-Indigo Girls
Isis-Bob Dylan
Baba O'Reilly-The Who
The End of the Innocence-Don Henley
What a Wonderful World

Posted by: princesspolitics | December 15, 2006 12:05 PM | Report abuse

Annie Lennox's Medusa album...the album to listen to if you need to get over a break-up.

Posted by: ckf | December 15, 2006 12:06 PM | Report abuse

Israel Kamakawiwo'ole covered Somewhere Over the Rainbow on a Ukele

Posted by: for mfd II | December 15, 2006 12:06 PM | Report abuse

"My Sh**'s F***ed Up" by Warren Zevon is a song he wrote just before he died about how his medications were no longer working, and his MD gave him a death sentence. Can't get much sadder because it was real.

Posted by: baikinange | December 15, 2006 12:06 PM | Report abuse

Yeah, the Smiths are a big one here. "I Know It's Over" just guts me every time:

Oh Mother, I can feel the soil falling over my head
and as I climb into an empty bed
Oh well. Enough said.
I know it's over-still I cling
I don't know where else I can go
Oh Mother, I can feel the soil falling over my head
see, the sea wants to take me
the knife wants to slit me
do you think you can help me?

Also, Pearl Jam's "Black":

I know someday you'll have a beautiful life
I know you'll be a star
In somebody else's sky, but why
Why, why can't it be, why can't it be mine?

Posted by: Simone | December 15, 2006 12:07 PM | Report abuse

In high school I broke up with a boyfriend and listened to Fiona Apple's "Never is a Promise" about one thousand times, just weeping.

pkc - I specifically make "Suicide Mix" CDs! How sick is that?!

Posted by: KG | December 15, 2006 12:07 PM | Report abuse

B-13 by Jump, Little Children, and about half of the Escucha CD by Laura Pausini, which is funny because I really have no idea what the lyrics translate into, but what. a. voice.

Posted by: Jeb | December 15, 2006 12:09 PM | Report abuse

Barry Manilow -- Time in New England
Kenny Logins and the Kermit version of Rainbow Connection
I forget who sings it -- New York Minute (post 9/11)
Celine Dion's version of All by Myself (the only Celine Dion song that I "liked" -- college break-up days)

Posted by: Thought of some more... | December 15, 2006 12:12 PM | Report abuse

Pearl Jam's version of "Last Kiss" (ditto) & "You've Got to Hide Your Love Away" - Eddie Vedder (from the I am Sam soundtrack)
--both make me choke up :(

Posted by: drea | December 15, 2006 12:13 PM | Report abuse

three that come immediately to mind:
The Smiths -- Asleep (lyrics sound like a suicide note)
Radiohead -- Let Down
Jeff Buckley -- Last Goodbye (made all the more sad by his untimely death)

Posted by: jimbo | December 15, 2006 12:14 PM | Report abuse

The smithereens had a couple of excellent sad songs - Blood & Roses, and Cigarette.
Elvis Costello - I Want You
I hope I'm not alone on this: Price - Purple Rain

Posted by: soGenX | December 15, 2006 12:16 PM | Report abuse

To Halleck23:

I agree -- "And the Band Played Waltzing Matilda" is one of the most depressing songs I have ever heard. I feel gloomy just thinking about it.

I would add to the list: Queen: "Who wants to live forever" and the opening of Mozart's Requiem.

Posted by: dornish sand | December 15, 2006 12:17 PM | Report abuse

Ferron's "Ain't Life a Brook."

I once was giving someone who had just dumped me a ride somewhere and put it on repeat. I swear that's the nastiest thing I've ever done, and the saddest song I've ever heard!

Posted by: eprice29 | December 15, 2006 12:18 PM | Report abuse

Dan Fogelberg - Same Auld Lang Syne
Our Lady Peace - Are You Sad?
Travis - Last Train (the song is more creepy than sad, but it is really depressing)

Simply Red's Holding Back the Years always makes me cry too

Posted by: McLean | December 15, 2006 12:18 PM | Report abuse

Neko Case - Dirty Knife
Depeche Mode - Black Celebration
and The Connells - Waiting My Turn

"i asked her to stay here with me a while
oh, she said "no"
these words mean nothing, these thoughts won't fly
oh, she said "no""

Posted by: chapelhillexpat | December 15, 2006 12:21 PM | Report abuse

Jimmy Eat World- 23
SheDaisy- Keep Me
Mazzy Star- Into Dust
Keane- Bedshaped (gorgeous song though)
Placebo- Running Up That Hill
Sia- Breathe Me
John Michael Montgomery- Letters From Home
Rascal Flatts- What Hurts the Most and Sarabeth
Coldplay- The Scientist (I think every high school student who graduated between 2002-2004 had it used in their "Remembrance" ceremony for all the students we lost.)
Death Cab For Cutie- I Will Follow You Into The Dark

And generally the really sad heart-wrenching must either be a) country b) sung by a woman with a gorgeous full voice or c) about a sad subject, done by either a) or b).

Posted by: Mason Patriot | December 15, 2006 12:22 PM | Report abuse

Hallelujah - the Jeff Buckley version
My Immortal - Evanescence
Crow on the Cradle - Jackson Browne
The Great Mandela - Peter, Paul and Mary
It's My Life - Bon Jovi (it's a divorce thing)
Gone out the Window (not sure if that's the right title) - Sugar Ray (another divorce thing)
Angel Eyes - Frank Sinatra
Not really sad, but will make me cry
My One and Only Love - Johnny Hartman and John Coltrane
Lush Life - Johnny Hartman and John Coltrane (the Joe Williams version is pretty good, too)
Taxi - Harry Chapin

Posted by: b | December 15, 2006 12:24 PM | Report abuse

maybe I'm too old and don't have the exact title, but I vote for "Cat's in the Craddle"

Posted by: ra | December 15, 2006 12:25 PM | Report abuse

How could I forget "Run" by Snow Patrol? Or "Acoustic #3" by Goo Goo Dolls! Finally, "Vermillion pt.2" by Slipknot. (Yes. Slipknot has a sad, depressing, slow song. I listen to it and immediately want to cry.)

I need to stop now.

Posted by: Mason Patriot | December 15, 2006 12:26 PM | Report abuse

And Seventeen by Janis Ian

Posted by: b | December 15, 2006 12:26 PM | Report abuse

Oh yeah, I forgot, almost everything by the smiths is depressing.

"I am human and I need to loooooved"

Sadly that song reminds me of the Breakfast Club and Judd Nelson's nostrils.

Posted by: not bluto | December 15, 2006 12:26 PM | Report abuse

"The Last Song" by Elton John, then one they play at the end of "And the Band Played On." I lose it.

Posted by: RRB | December 15, 2006 12:27 PM | Report abuse

Lydia - by Slaid Cleaves

Posted by: rae | December 15, 2006 12:29 PM | Report abuse

Camera - REM
Washing of the Water - Peter Gabriel
The Only One - Billy Bragg
One Step Up - Bruce Springsteen
This Woman's Work - Kate Bush

Posted by: David S. | December 15, 2006 12:30 PM | Report abuse

The saddest song in the world is Willie Nelson's "You Were Always On My Mind".

No changes, no nuthin's.

Posted by: Fairfax | December 15, 2006 12:31 PM | Report abuse

Wait, how in the world is Wicked Game by Chris Isaak sad????

Isn't it, um, exciting???

Posted by: not bluto | December 15, 2006 12:31 PM | Report abuse

It sounds stupid but Puff the magic dragon always gets me.

Posted by: dmi | December 15, 2006 12:33 PM | Report abuse

You're all amazing. This list is rich enough to populate an iPod exclusively for sad songs.

Posted by: Liz | December 15, 2006 12:33 PM | Report abuse

I think it's by the Gin Blossoms, but "One Headlight" makes me sad....

Posted by: Anonymous | December 15, 2006 12:34 PM | Report abuse

Gosh, what a nice roommate you have Liz. When my college boyfriend dumped me, my roommate played Chicago's greatest hits CD everynight as we went to bed. Those were hard days...

Posted by: Emmy | December 15, 2006 12:36 PM | Report abuse

I love you people.

If were were on Leslie's Comments Blog ("On Balance"), you would all be trying to make each other feel bad about your choices.

After reading that blog's comments, people need these sad songs.

Posted by: klj | December 15, 2006 12:38 PM | Report abuse

What awesome songs you guys have listed!
James Taylor - Fire & Rain (admit that in college [!] I shared a bottle of wine with a friend and we balled when this came on the stereo
Beatles -- In My Life (same friend, years later, another bottle of wine, but this time the song was on a CD and not vinyl)
Terry Jacks -- Seasons in the Sun (when I was little, I made up an interpretive dance to this, my mother sat in the livingroom and applauded when I was done, tears streaming down her face, and now I cry whenever I hear it on the muzak)
Jeff Buckley -- Grace [album and song] (it's a sad suicidey song, unfortunately will always be linked to my first car accident, I drove the car into a light pole and totaled the car, and YES it was an accident; the silver lining of the accident was I quit smoking while behind the wheel, eventually quit smoking all together)

Posted by: miss belle | December 15, 2006 12:39 PM | Report abuse

Wow, how is Billie Holiday missing from the list? Good Morning Heartache, Lover Man, I Gotta Right to Sing the Blues, One for My Baby, God Bless the could go on and on. Great music.

Posted by: Vienna | December 15, 2006 12:41 PM | Report abuse

* Bell Bottom Blues - Derek and the Dominoes
* Most of the Time - Bob Dylan
* I Just Don't Think I'll Ever Get Over You - Colin Hay
* It Makes No Difference - The Band (Rick Danko's vocals DO make a difference).

Posted by: Martin | December 15, 2006 12:44 PM | Report abuse

Oh, and I forgot the entire soundtrack to "Until The End of The World," the awesome Wim Wenders movie.
Calling All Angels by Jane Sieberry and kd lang, Days by Elvis Costello, and Death's Door by Depeche Mode are particularly hard for me to listen to, as this movie/album came out around the time of my sister's death.
Do yourself a favor, at the very least see the movie. William Hurt at his squintiest-best!

Posted by: miss belle | December 15, 2006 12:45 PM | Report abuse

Ooh, this is a great topic, and some really good choices so far!

Joni Mitchell - "River" and "Blue"
Kingston Trio - "Where Have All the Flowers Gone?"
Ani DiFranco - "Both Hands" and "When I'm Gone"
Des'ree - "Kissing You"
Jeff Buckley - "Hallelujah"
Cat Power - "Colors and the Kids"
Sarah Maclachlan - "Good Enough"

When you feel like a dose of high school-style melodramatic angst, pretty much anything by Dashboard Confessional works, especially "Age Six Racer," and Saves the Day's "At Your Funeral."

Posted by: R | December 15, 2006 12:45 PM | Report abuse

a few more

Soul Asylum -- "Runaway Train" (at least when combined with the video)
John Lennon and Yoko Ono -- "Watching the Wheels" (for me at least, will always be associated with his murder)

and from the same era as "Wildfire":
Eric Carmen -- "All By Myself", or "Never Gonna Fall In Love Again", take your pick...

Posted by: jimbo | December 15, 2006 12:46 PM | Report abuse

"One Headlight" was by Jakob Dylan and the Wallflowers.

Posted by: Arlington, VA | December 15, 2006 12:48 PM | Report abuse

Absolutely saddest song:
Wild and Lonely by the Associates.
But close second 'Gloomy Sunday' by ..well most bands/singers that have covered this song.
Aldo known as 'The Suicide Song'

Posted by: G | December 15, 2006 12:49 PM | Report abuse

"Hello in There" John Prine
"I Think It's Going to Rain Today" Randy Newman

Posted by: clq76 | December 15, 2006 12:49 PM | Report abuse

Bonnie Raitt's "Make You Love Me"
Julie London's "Cry Me A River"
Robbie Williams's "Eternity"
Sarah Bettens's "All Of This Past"
and Aimee Mann's "Save Me"

I could keep going, but I'm sad already.

Posted by: loonatic | December 15, 2006 12:50 PM | Report abuse

Elvis Costello-"God Give Me Strength"
The Who-"Cut My Hair" from Quadrophenia
Johnny Cash-"The Beast in Me"

Sad in different ways. I get something new out of them each time I listen.

Posted by: Barb | December 15, 2006 12:51 PM | Report abuse

A few more:

Alison - Elvis Costello

Backstreets and Meeting Across the River - Bruce Springsteen

Posted by: Martin | December 15, 2006 12:54 PM | Report abuse

"Love Hurts" - the Gram Parsons/Emmylou Harris version.

Posted by: Tony | December 15, 2006 12:55 PM | Report abuse

Wait, I totally forgot Evanescence's "My Immortal".

And "Nan's Song" by Robbie Williams. Of course, I'm pretty sure that it's impossible to write a song about your beloved grandmother's death without it qualifying for inclusion in a "saddest songs ever" list.

Posted by: loonatic | December 15, 2006 12:55 PM | Report abuse

I can't believe with all the mentions of Aimee Mann, I forgot "Voices Carry."

Oh, and currently listening to Concrete Blonde's "Joey" on my iPod as I produce this afternoon's Carolyn Hax holiday chat.

All hail '80s sentiment!

Posted by: Liz | December 15, 2006 12:55 PM | Report abuse

When my college boyfriend dumped me suddenly, on his birthday, after I drove an hour and a half to bring him home; I locked myself in my room and played "Melissa" by the Allman Brothers over and over. Ironically, I named my youngest daughter after that song 12 years later.

Posted by: Laina | December 15, 2006 12:58 PM | Report abuse

I agree with halleck23, The Band Played Waltzing Matilda is a sad song but I like Makem and Clancy's version best, they actually sing all of my favorite sad song...Willie McBride (fab. anti-war song), Peter Kagen and the Sea, The Dutchman. But if we're going for the Pogues The Fairytale of New York is wonderful for the season and for it's melancholy combo of hope and loss.

Posted by: The Ocho | December 15, 2006 12:59 PM | Report abuse

Oh, and another: Bauhaus's "All We Ever Wanted."

Okay, I'll stop hijacking the comments thread now.

Posted by: Liz | December 15, 2006 12:59 PM | Report abuse

fade into you - Mazzy Star
My Immortal - Evanescence
Cooling - Tori Amos
Possession - Sarah Maclachlan
Street Spirit - Radiohead

Posted by: Jimmy | December 15, 2006 1:01 PM | Report abuse

"It Was a Very Good Year" -- Frank Sinatra
"In My Room" -- Beach Boys
"Salty Dog" -- Procol Harum
"Sky Pilot" -- The Animals
"Goodnight Saigon" -- Billy Joel
"Rooster" -- Alice in Chains
"The Wreck of the Edmund Fitzgerald" -- Gordon Lightfoot
"Don't Give Up" -- Peter Gabriel
"Summer Skin" -- Death Cab for Cutie

Posted by: rich | December 15, 2006 1:02 PM | Report abuse

I agree with halleck23 about "Waltzing Matilda" but it's "Fairytale of New York" by The Pogues and Kirsty MacColl that really gets me.

"A Pair of Brown Eyes" (also the Pogues) is a killer too.

Posted by: Emmie | December 15, 2006 1:04 PM | Report abuse

Tracy Nelson and Mother Earth - "Down So Low" Excellent song for when you're in the depths of despair from a relationship break up.

For people who enjoy songs other than rock music:

Emmylou Harris - "Calling My Children Home" - sad in that "Tears From Heaven" way. And I don't even like children.

Doc Watson or Lucinda Williams (I think she covered it, too) - "Farther Along"

Posted by: Cubeland | December 15, 2006 1:04 PM | Report abuse

hands down, saddest cd on the planet (the whole thing, every song) - berlin by lou reed. i tell everyone, if you already blue and just want to cry and cry, put berlin on.

Posted by: kelly | December 15, 2006 1:04 PM | Report abuse

Jeez, how could I forget The Mountain Goats--No Children.

Posted by: The Ocho | December 15, 2006 1:05 PM | Report abuse

Richard Marx - Right Here Waiting for You

I lived oversees (in college) and my boyfriend was here in the U.S. and that song used to make me bawl, and then even more when we broke up.

Also, Bette Middler's "Wind Beneath My Wings." That's a tearjerker.

Posted by: AJ | December 15, 2006 1:06 PM | Report abuse

Ah, you beat me to it The Ocho - did you happen to see the Pogues at the 9:30 club last year? Jem Finer's daughter came out and sang Fairytale with Shane. I managed not to completely lose it, but I was close!

Posted by: Emmie | December 15, 2006 1:07 PM | Report abuse

Rufus Wainwrigt- hallelujah

Kenny Logins - House in Pooh Corner - it makes me sad that I'm not a little kid and reminds me of my da.

Posted by: mfd | December 15, 2006 1:09 PM | Report abuse

I can't belive it, I have an original Thought and song: Hopeless by Dionne Farris. "I'm hopless like a penny with a hole in it"

Posted by: BB | December 15, 2006 1:16 PM | Report abuse

We really need a happy song in here fast. Reading this list is so sad!

Posted by: oh geez | December 15, 2006 1:16 PM | Report abuse

It may seem a little odd..

TOOL-"Schizm" "H"
Korn-"Throw Me Away"
Most anything by The Smashing Pumpkins

Hunh, something about heroin seems to make peopel really sad

Posted by: EricS | December 15, 2006 1:16 PM | Report abuse

Quote: Oh yeah, I forgot, almost everything by the smiths is depressing.

"I am human and I need to loooooved"

that would be "how soon is now."

U2: With or Without You

Posted by: SS | December 15, 2006 1:20 PM | Report abuse

It's a religious song, but I cannot get through "How Great Thou Art" without a large lump in my throat.

Posted by: Elizabeth | December 15, 2006 1:22 PM | Report abuse

Kind of random, and not a "popular" song, but La Mamma Morta, sung by Maria Callas on the Philadelphia soundtrack always leaves me bawling . . .

Posted by: PartyGirl | December 15, 2006 1:23 PM | Report abuse

Sorry to be disagreeable, but Israel Kamakawiwo'ole's version of Over the Rainbow/What a Wonderful World is SO not a sad song!

I think Gram Parsons singing "Love Hurts" is soooo sad.

Posted by: soso | December 15, 2006 1:23 PM | Report abuse

Two songs that haven't been mentioned are

U2: Wake Up Dead Man
Death Cab for Cutie: Transatlanticism

Posted by: Wobig | December 15, 2006 1:32 PM | Report abuse

I can't believe U2 has not made the list. "One" and "With or Without You" are classic sad songs.

Posted by: jcs | December 15, 2006 1:32 PM | Report abuse

You don't know from sad until you've heard G.C. Cameron's So Hard to Say Goodbye to Yesterday. Ignore Boyz II Men's upbeat version. The haunting music and lyrics are a quick roller coaster ride to sadville if you're not careful. Most are oldies but very effective for a pity party of 1.

Enchantments - Gloria
Mahalia Jackson - Trouble of the World
Phyllis Hyman - Living All Alone
O'Jays - Cried Together
Dru Hill - We're not Making Love No More
Most of Sade's catalog

Posted by: db | December 15, 2006 1:33 PM | Report abuse

I agree with Leonard Cohen's "Hallelujah" sung by Jeff Buckley

Also, "Without You" by Nilsson, and "Ashokan Farewell" by Jay Unger - gets me every time.

Posted by: lafred | December 15, 2006 1:34 PM | Report abuse

Hahaha Joey by concrete blonde!

Is All is Full of Love, by Bjork sad?

Posted by: not bluto | December 15, 2006 1:38 PM | Report abuse

The songs that always make me cry are:

U2 - Sometimes you can't make it on your own

Joni Mitchell - River

Posted by: Kat | December 15, 2006 1:40 PM | Report abuse

Typo of the day, courtesy of Miss Belle:

"James Taylor - Fire & Rain (admit that in college [!] I shared a bottle of wine with a friend and we balled when this came on the stereo"

But wouldn't that be a happy memory?

Posted by: Nameless One | December 15, 2006 1:45 PM | Report abuse

I want to know how there is a blog on sad songs and the Cure was not mentioned once. What's up with that?

How about Elliot Smith? Anybody who stabs themselves to death ought to at least get a nod.

And just a note. Via Chicago is about a break up, but it's about his old band... at least that's what I heard. And when I hear things, I accept them as truth without attempting to verify.

Also, there was this song on a game called "Teddy Boy" I had for my Sega Master System.. it made me cry. It wasn't even sad, it was just the right series of electronic blips to really stir my emotions. Plus I was five. Not to mention the song that was the theme for the movie version of "My Side of the Mountain." Man did that ever get to me. Especially after -sniff- the hunter.. killed his Peregrine falcon. And they just HAD to show that in my sixth grade class the week my own Parakeet was tragically smushed in the refrigerator.

RIP Buddy Bird

Posted by: what?!? | December 15, 2006 1:46 PM | Report abuse

"Tears in Heaven" is by far the saddest I can think of

For Christmas it has to be "Do They Know it's Christmas" (...tonight thank God it's them instead of you...) really, how depressing is that?

Posted by: jes | December 15, 2006 1:47 PM | Report abuse

A sad song for me that fortunately is not played much is "19". Don't know who sang/spoke it but it relates that the average enlisted age of men in Vietnam was 19; in WWII the average age was 26. Listen to that and then go to the Vietnam memorial and I guarantee you'll lose it!

Already mentioned is "The Last Song" by Elton John.

Showing my age again but does anyone remember "Scarlet Ribbons"? A poor father overhears his little girl asking God for scarlet ribbons for her hair. Of course, daddy couldn't afford them and, of course, the next morning the ribbons appeared. Used to make me boo-hoo every time!

Posted by: pnina | December 15, 2006 1:47 PM | Report abuse

Okay, still listening to the iPod. Did anyone add Elvis Costello's "She" yet?

Posted by: Liz | December 15, 2006 1:54 PM | Report abuse

Props to whoever first mentioned "Fairytale of New York" -- I tend towards the cynical, but this song NEVER fails to grab my heart and take me for a ride. It tells a complete story about two people that is sad, depressing, funny, and uplifting all in less than 5 minutes.

Sing along, everyone: "The boys of the NYPD choir were singing 'Galway Bay'/And the bells were ringin' out for Christmas Day. . ."

Posted by: Doc | December 15, 2006 1:57 PM | Report abuse

Bob Dylan's "If You See Her, Say Hello."

The line "Say for me that I'm alright, though things get kind of slow/She might think that I've forgotten her, don't tell her, it isn't so" pretty well sums it up.

In fact, the whole Blood on the Tracks album is pretty damn depressing, though it's also one of the best records ever made.

Posted by: NJ | December 15, 2006 1:59 PM | Report abuse

Totally agree with Into the Dark by Death Cab for Cutie.
Jimmy Buffett: Coast of Marseilles
Beach Boys: Caroline, no
Eagles: Best of my love

This is a great topic!

Posted by: seattlemom | December 15, 2006 1:59 PM | Report abuse

"Moving on a Holiday" - Freedy Johnston
"Family Life" - Blue Nile

Posted by: TSH | December 15, 2006 2:03 PM | Report abuse

"December" by the Counting Crows. yeah, a boyfriend-association...a 4-year relationship down the drain and it ended in December, right around when the song came out. still kindof gets to me, but at least I can get through the song nowadays.

Posted by: bunny girl | December 15, 2006 2:03 PM | Report abuse

I've got a lot of favorites and most have them been mentioned but I just got Teddy Thompson's (Richard's son) new CD Seperate Ways and his songs:

I Should Get Up
I Wish It Was Over
Separate Ways
Sorry To See Me Go
Think Again

Just bring back so much...

Posted by: wdtcm | December 15, 2006 2:03 PM | Report abuse

"And So It Goes" by Billy Joel
"Angel from Montgomery" by John Prine (and sung by Bonnie Raitt)
Alone Again, Naturally" by Gilbert O'Sulivan
"Misty Blue" by Dorothy Moore
"I know" by Fiona Apple
"No Easy Way to Cry" by David Gray
"Christmas Card from a Hooker in Minneapolis" by Tom Waits

"Jolene" by Ray LaMontagne is probably one of the saddest songs I've ever heard

Posted by: Christofornio | December 15, 2006 2:04 PM | Report abuse

Sugar Mountain - Neil Young
Find the Cost of Freedom - Crosby, Stills, Nash & Young
To the Last Whale: Critical Mass/Wind on the Water - David Crosby and Graham Nash
Dreams - Allman Brothers
Even in the Quietest Moments - Supertramp
Paradise - John Prine
Sunset Grill - Don Henley
Where Have All the Flowers Gone - Pete Seeger
Puff the Magic Dragon - Peter, Paul & Mary

Posted by: RK | December 15, 2006 2:05 PM | Report abuse

So You Say by Manhattan Transfer

Posted by: b | December 15, 2006 2:07 PM | Report abuse

Boys of Summer by Don Henley

Posted by: b | December 15, 2006 2:09 PM | Report abuse

Josh Rouse, My Love Has Gone

The Jayhawks, Crowded in the Wings

Neil Young, Helpless

The Band, It Makes No Difference

Damien Jurado, Ohio

Posted by: Anonymous | December 15, 2006 2:09 PM | Report abuse

Remembering a few more...

Pretty much any Elliot Smith song will do the trick, but "Needle in the Hay" and "Say Yes" are my miserable favorites.

"Abraham, Martin and John" is one of the saddest songs I've ever heard - and I grew up in the '80s!

Bonnie Raitt - "I Can't Make You Love Me"
Verve Pipe - "The Freshman"
Jude - "I Do" (makes me cry almost every time, especially if I have a glass of wine beforehand)

Posted by: R | December 15, 2006 2:10 PM | Report abuse

Patsy Cline - walkin after midnight

Posted by: not bluto | December 15, 2006 2:12 PM | Report abuse

I always thought that Iz's rendition of Rainbow/What a Wonderful World was beautiful and mesmerizing.

This hero of Hawaii died young, about 10 years ago. He was known to everyone as a "gentle giant" with a constant good cheer.

Over 20,000 people attended his memorial service; and for the only third time in state history, the Hawaiian flag flew at half mast over the state capitol.

There's a vid of Iz performing Rainbow, and the memorial service, available on YouTube. Warning- it's touching, so you might want to have a tissue ready.

Posted by: Mikopedia | December 15, 2006 2:13 PM | Report abuse

Auugggghhh! I forgot the saddest song of all time...

I'm So Lonesome I Could Cry - Hank Williams

There's also an even more gut-wrenching version of that by Keb Mo

Posted by: Christofornio | December 15, 2006 2:17 PM | Report abuse

Yes, Bluto, "All Is Full of Love" is a sad one. (There is an equally sad cover of it by Death Cab as well.)

Elliott Smith is a good call too, "Needle in the Hay". "Miss Misery" and others. Speaking of needles, "The Needle and the Damage Done" is pretty sad. And since I don't think anyone's mentioned any other Neil Young to this point, I'd add "Powderfinger" to the list too.

Posted by: jimbo | December 15, 2006 2:18 PM | Report abuse

Missing - Springsteen
Missing You - The Mavericks
Just about anything by Leonard Cohen aka "Songs to Slit Your Wrists"

Posted by: Rowdy Yates | December 15, 2006 2:21 PM | Report abuse

Bonnie Raitt - Matters of the Heart, not crying, just reach for the bottle

Eva Cassidy - Tall Trees of Georgia, even if you don't know she was dying and saying goodbye to her parents

Simon and Garfunkle - Sounds of Silence, even Muzak (tm) can't totally kill it

Posted by: old guy | December 15, 2006 2:25 PM | Report abuse

How about John Prine's "Sam Stone"

There's a hole in daddy's arm where all the money goes,
Jesus Christ died for nothin' I suppose.
Little pitchers have big ears,
Don't stop to count the years,
Sweet songs never last too long on broken radios.

Posted by: Mikopedia | December 15, 2006 2:28 PM | Report abuse

Re Sam Stone, I'll do you one better:

Sam Stone was alone
When he popped his last balloon
Climbing walls while sitting in a chair
Well, he played his last request
While the room smelled just like death
With an overdose hovering in the air

Posted by: Sam Stone | December 15, 2006 2:30 PM | Report abuse

No Retreat, No Surrender - Springsteen
The Rising - Springsteen
Fields of Gold - Sting
Me and Bobbi McGee - Kristofferson

Posted by: Kate | December 15, 2006 2:31 PM | Report abuse

Dan Fogelberg - Same Auld Lang Syne

This gets me every time - I have to pull over the car.

Posted by: Anonymous | December 15, 2006 2:31 PM | Report abuse

I agree, " And the Band played Waltzing Matilda" is among the top saddest songs ever. I have it by Joan Baez, who also sang "Birmingham Sunday", about the Alabama church bombing. Pretty depressing too. Dylan's The Ballad of Hollis Brown should probably be on the list. Simon and Garfunkel's Old Friends is pretty sad too.

Posted by: tdp | December 15, 2006 2:36 PM | Report abuse

Amazing that I read through almost a hundred posts before I got to the saddest song I can think of:

CAROLINE NO by the Beach Boys

Just a beautiful heartbreaking record. That "Ohh, Caroline nooooooooo" at the end where his voice goes high just gets me every time.

Some of these picks cross the line from "sad" to "depressing." "For No One" by the Beatles is sad; "Eleanor Rigby" is depressing.

"Angel Eyes" by Sinatra is a good one; "Suspicious Minds" by Elvis is a good one. And I think that the one person who said "pretty much anything by George Jones" is definitely on to something: "She Thinks I Still Care" would be in my top ten too.

Great topic.

Posted by: Margo | December 15, 2006 2:36 PM | Report abuse

Nobody mentioned Taylor Hicks' Do I Make You Proud??????

(Tho' his Dancin' in the Streets makes me cry with laughter).

Posted by: not bluto | December 15, 2006 2:37 PM | Report abuse

Bronski Beat "Small Town Boy"
Smithereens "Lonely Place"
Pink Floyd "Wish You Were Here"

BTW, "One Headlight" is the Wallflowers, not Gin Blossoms.

Posted by: Rasputin | December 15, 2006 2:37 PM | Report abuse

You've Lost that Lovin Feeling has the saddest lyrics, but happy-ish music. And ever since Tom Cruise sang it in Top Gun, people sing it to each other all the time, but if you listen to the words, it's really pretty depressing. Who hasn't been there?

Posted by: Sad Song that No One seems to know is Sad | December 15, 2006 2:38 PM | Report abuse

The saddest song I can think of is not even a "sad" song, but hearing it breaks my heart every time: "(Just Like) Starting Over" by John Lennon always reminds me of autumn 1980, and how great it felt to hear John Lennon back on the radio with new music after five years... a record full of hope and joy that jumped out of the radio every time it played... and then all of it destroyed on December 8. I still feel deeply deeply sad every time I hear that record.

Posted by: Max | December 15, 2006 2:39 PM | Report abuse


Oh amen. That song absolutely kills me.

Others that tear me up:
Tangerine--Led Zeppelin
Hallejujah--Rufus Wainwright version
The freakin theme from Brokeback
One Moment More--Mindy Smith

Posted by: lizpoppe | December 15, 2006 2:40 PM | Report abuse

Lydia. Lydia is the song that kills me.

Posted by: lizpoppe | December 15, 2006 2:43 PM | Report abuse

Auugggghhh! I forgot the saddest song of all time...

I'm So Lonesome I Could Cry - Hank Williams

There's also an even more gut-wrenching version of that by Keb Mo

Posted by: Christofornio | December 15, 2006 02:17 PM
Yes, yes, yes, Christofornio! You are correct. "I'm So Lonesome . . . " IS the saddest in the world.

("You Were Always On My Mind" is second, however.)

Posted by: Fairfax | December 15, 2006 2:45 PM | Report abuse

Warren Zevon: Keep Me in Your Heart (written near the end of his life, pleading with his family not to forget him)

Smiths: Please Please Please Let Me Get What I Want (lyrics--"Lord Knows It Would Be the First Time")

The Cure: A Thousand Hours (lyrics: "How Much Longer Can I Cry Like This")

Johnny Cash's cover of Hurt by NIN (the video is downright hard to watch)

Annie Lennox: Why

Posted by: Sarah | December 15, 2006 2:46 PM | Report abuse

Ryan Adams, the whole "Heartbreaker" album. The title says it all.

Also, "Betterman" by Pearl Jam.

Posted by: GoBlue girl | December 15, 2006 2:50 PM | Report abuse

I'm surprised some sap didn't mention Unchained Melody

Posted by: not bluto | December 15, 2006 2:55 PM | Report abuse

Pearl Jam's Black. Cry every time, to this day. And I wasn't even going through a breakup when it was most popular.

Posted by: NoShowMo | December 15, 2006 2:56 PM | Report abuse

It was Chrismas Eve, babe
In the drunk tank
An old man said to me
Won't see another one....

And glory be to the righteous who've pointed out "And The Band Played Waltzing Matilda". Gut shot.

Posted by: Mikey T | December 15, 2006 2:57 PM | Report abuse

I'd have to vote for:

"Crying" by Roy Orbison (particularly the version he sings with k.d. lang)
"She Was the Prize" by Gaelic Storm
"Don't Cry Daddy" by Elvis
"That's the Way I've Always Heard it Should Be" by Carly Simon. I remember listening to that tape (!) on drives between home and college and being so afraid of having regrets.

Posted by: pigelot | December 15, 2006 2:58 PM | Report abuse

Alan Parsons - "Sooner or Later"
Alanis Morissette - "Unsent"
Alphaville - "Forever Young"
Annie Lennox - "Walking on Broken Glass"
Billy Joel - "Summer, Highland Falls"
Bon Jovi - "You Give Love a Bad Name"
Bryan Adams - "Cuts Like a Knife"
Carole King - "So Far Away"
Carrie Underwood - "Lessons Learned"
Cat Stevens - "Wide World"
Cathie Ryan - "Garden Valley"
Celine Dion - "Coulda Woulda Shoulda"
Cherish the Ladies - "The Broom of the Cowdenknowes"
Cheryl Wheeler - "This Is Me"
Chicago - "Look Away"
Clay Aiken - "Invisible"
Crosby, Stills, Nash, and Young - "Southern Cross"
Dar Williams - "When I Was a Boy"
Def Leppard - "Love Bites"
Dido - "White Flag"
Dire Straits - "Romeo and Juliet"
Dixie Chicks - "Travelin' Soldier"
Dougie Maclean - "Caledonia"
Eric Carmen - "All By Myself"
Eurythmics - "17 Again"
Fred Small - "The Heart of the Appaloosa"
George Winston - "Variations on the Kanon by Pachelbel"
Gordon Lightfoot - "The Wreck of the Edmund Fitzgerald"
Holly Near - "Uh Huh"
Hootie and the Blowfish - "Let Her Cry"
Howard Shore - "The Steward of Gondor"
Indigo Girls - "Ghost"
James Taylor - "Fire and Rain"
Jamie O' Neal - "There Is No Arizona"
Janis Ian - "At Seventeen"
Jethro Tull - "Wond'ring Aloud"
John Denver - "Leaving on a Jet Plane"
John Mayer - "My Stupid Mouth"
Jonathan Coulton - "Not About You"
Joni Mitchell - "Both Sides Now"
Journey - "Separate Ways"
Juliana Hatfield - "Feelin' Massachusetts"
Kenny Loggins - "Heart to Heart"
Kimberley Locke - "I Can't Make You Love me"
Lisa Moscatiello - "Nightbird"
Mamas and Papas - "California Dreamin'"
Mary Black - "I Live Not Where I Love"
Mary Chapin Carpenter - "The Dreaming Road"
Melissa Etheridge - "Tuesday Morning"
Nanci Griffith - "Once in a Very Blue Moon"
Neil Young - "Ohio"
Nickel Creek - "When You Come Back Down"
Pink Floyd - "Comfortably Numb"
Rascal Flatts - "Prayin' For Daylight"
Savage Garden - "Crash and Burn"
Shania Twain - "Nah!"
SheDaisy - "Get Over Yourself"
Simon and Garfunkel - "I Am a Rock"
Stephen Bishop - "On and On"
Sting - "Mad About You"
Sugar Ray - "Is She Really Going Out with Him?"
Supertramp - "Take the Long Way Home"
Suzanne Vega - "The Rent Song"
The Beatles - "Yesterday"
The Chieftains - "A Stor Mo Chroi"
The Corrs - "What Can I Do?"
The Cranberries - "I Can't Be with You"
The Moody Blues - "Your Wildest Dreams"
The New St. George - "All the Tea in India"
The Rolling Stones - "You Can't Always Get What You Want"
The Thompson Twins - "Hold Me Now"
They Might Be Giants - "Don't Let's Start"
Tim McGraw - "For a Little While"
Tom Petty and the Heartbreakers - "Don't Do Me Like That"
Tori Amos - "God"
Trisha Yearwood - "The Song Remembers When"
U2 - "With or Without You"
Vanessa Carlton - "A Thousand Miles"
Wilson Phillips - "Eyes Like Twins"
Yes - "Owner of a Lonely Heart"

Posted by: Since You Asked... | December 15, 2006 3:01 PM | Report abuse

Angel by Massive Attack, you would think it would be uplifting with lyrics like "you are my angel" but the beat says different.

Posted by: petal | December 15, 2006 3:03 PM | Report abuse

Homeward Bound- Simon and Garfunkel
Do You Realize? - Flaming Lips
Pictures of You- The Cure
Fix You- Coldplay
Glory Days- Bruce Springsteen
Knockin on Heaven's Door/ You're Gonna make me Lonesome when you Go- Bob Dylan
Bed of Roses- Bon Jovi

Saddest breakup song: In your Wildest Dreams by Moody Blues. Wow.

Did anyone list "Sleep" by Dandy Warhols?

"if I could sleep forever
but it's of her i dream
if i could sleep forever
i could forget about everything"

Posted by: LR | December 15, 2006 3:03 PM | Report abuse

GREAT suggestions!

I'll try to add a few that I ahve not seen. It's okay to snicker if you think my selections are passe or require an insulin injection.

Same Old Tears on a New Background by Stephen Bishop. Art Garfunkel cover is better, IMO.

Tom Traubert's Blues by Tom Waits

Ruby's Arms by Tom Waits

And a number of songs by Randy Newman, including:

Texas Girl at the Funeral of Her Father

Real Emotional Girl

Every Time It Rains

Living Without You

Louisiana 1927

And the biggest downer of a tune I've EVER hear, also by Randy Newman:

Old Man

Everyone has gone away
Can you hear me? Can you hear me?
No one cared enough to stay
Can you hear me? Can you hear me?
You must remember me old man
I know that you can if you try
So just open up your eyes, old man
Look who's come to say goodbye

The sun has left the sky, old man
The birds have flown away
And no one came to cry, old man
Goodbye, old man, goodbye

You want to stay, I know you do
But it ain't no use to try
'Cause I'll be here-and I'm just like you
Goodbye, old man, goodbye

Won't be no God to comfort you
You taught me not to believe that lie
You don't need anybody
Nobody needs you
Don't cry, old man, don't cry
Everybody dies

Posted by: Mister Methane | December 15, 2006 3:05 PM | Report abuse

No one said No Doubts "Don't Speak?" Amazing.

Posted by: Rockville | December 15, 2006 3:05 PM | Report abuse

P Diddy/Puff Daddy whatever he was at the time -- Missing You

Ditto for Auld Lang Syne and Puff the Magic Dragon.

Also, not really a "main-stream" song, but the song from Dumbo when the mamma elephant is taken away...

Billy Joel -- Lullabye, If Only I Had the Words to Tell You, Honesty

Josh Groban -- You Raise Me Up only because they played it a lot after the space shuttle accident a few years back

Posted by: Anonymous | December 15, 2006 3:06 PM | Report abuse

tearjerkers by the legendary Neil Diamond:
"Hello Again"
" I Am, I Said"

Posted by: LRN | December 15, 2006 3:10 PM | Report abuse

Beatles. Yesterday. Surprised it hasn't been mentioned.

Posted by: Oldie but goodie? | December 15, 2006 3:10 PM | Report abuse

Thank you, Mikey T.

Posted by: Anonymous | December 15, 2006 3:14 PM | Report abuse

Tom Waits' "Martha"

"And those were the days of roses,
poetry and prose and Martha
all I had was you and all you had was me.
There was no tomorrows,
we'd packed away our sorrows
And we saved them for a rainy day."

Posted by: TW | December 15, 2006 3:14 PM | Report abuse

Not just a song, a whole album, the Counting Crows' "August and Everything After." It litterally put me into a funk for a good quarter of the ninth grade.

Posted by: Anonymous | December 15, 2006 3:16 PM | Report abuse

oh yeah, I forgot

Simon and Garfunkel "America" how sad. I listen to it to feel sorry for myself for never having gone on a bus tour of America while playing silly games with my special lady.

Posted by: what?!? | December 15, 2006 3:17 PM | Report abuse

Almost anything at all by Eva Cassidy: Songbird and Over the Rainbow especially.

Feels like Home To Me - Bonnie Raitt

Desperado - Eagles

Angel - Sarah MacLachlen

Grace - the Irish folk song about Joseph Plunkett and Grace Grifford marrying in the Kilmainham Jail prison the day before he is executed by firing squad for his part in the Easter Uprising

Leaving Nancy - Eric Bogle

In My Life - Beatles

Have I told You Lately - Rod Stewart or Van Morrison

Distant Thunder - Mack Bailey

Would You Know My Name If I Saw you in HEaven - Eric Clapton

Crazy - Patsy Cline

Both Sides Now - the most recent version by Joni Mitchell

That's all I can think of now -- I think I'll crawl into a glass of wine, or 2 or 3.

Posted by: Southern Maryland | December 15, 2006 3:18 PM | Report abuse

"No Woman, No Cry," though a song of consolation, I guess, always makes me cry. Thick with nostalgia and loss. "My feet is my only carriage, so I got to push on through."

Posted by: a few more | December 15, 2006 3:21 PM | Report abuse

Another great heartbreaker is Paul Simon's song about John Lennon--"The Late Great Johnny Ace."

Posted by: Silver Spring | December 15, 2006 3:23 PM | Report abuse

I'm glad someone mentioned Eva Cassidy. There are so many songs of hers that could fit here. I'll mentioned 2 - Fields of Gold and American Tune.

A sad song for this holiday season, Coventry Carol. Joan Baez sings it beautifully on her Noel album, recorded in 1966. (For you PDQ Bach fans, Peter Schickele did the arrangements for all the music on this album)

Posted by: mary ann | December 15, 2006 3:24 PM | Report abuse

And Beth Orton's "Concrete Sky." Her voice is heartbreaking, and the lyrics make me so sad.

I'm going to have to get to work on iTunes and make me some depressing mixes . . . .

Posted by: Northerner | December 15, 2006 3:34 PM | Report abuse

Um, Paul Simon's 'The Late Great Johnny Ace' is *primarily* about 50's R&B singer Johhny Ace and only partially, and to a lesser degree about John Lennon.

Posted by: Marsh Man | December 15, 2006 3:36 PM | Report abuse

Apron Strings - Everything But the Girl

Everything I Own - Bread

Bless the Weather - John Martyn

Posted by: CK | December 15, 2006 3:39 PM | Report abuse

Ok, I'll say it. Folks, there is a fine line between sad and cheesy.

Posted by: Anonymous | December 15, 2006 3:40 PM | Report abuse

Also, "She Misses Him" about Nancy Reagan handling her husband's alzheimer's. The first time I heard it I listened with tears running down my face.

Posted by: CK | December 15, 2006 3:40 PM | Report abuse

Bookends by Simon and Garfunkel brings a tear. How about cheery songs, or silly dance pop or something next Friday?

Posted by: meg | December 15, 2006 3:43 PM | Report abuse

Goo Goo Dolls - Iris ("you bleed just to know you're alive")
Third Eye Blind - How's It Going to Be
Frank Sinatra - One for My Baby (one more for the road)
Everybody Hurts - REM

Posted by: ex cap girl | December 15, 2006 3:48 PM | Report abuse

"The Queen and the Soldier", Suzanne Vega:

"Out in the distance her order was heard,
and the soldier was killed, still waiting for her word.
And while the queen went on strangling in the solitude she preferred,
the battle continued on."

Her whole first album, come to think of it, is rather depressing. Beautiful and haunting, but depressing.

Runner-up: David Sylvian, "Nostalgia"

Posted by: Aynthem | December 15, 2006 3:51 PM | Report abuse

"Tears In Heaven" makes me want to go home, fold my toddler in my arms, and never ever let go. Parenthood (and knowing the story behind the song) puts it into a whole new world of emotional.

Posted by: Jeb | December 15, 2006 3:59 PM | Report abuse

My favorite sad song is Duke Ellington's "I've got it bad and that ain't good" I've heard several versions, but no one beats Dianne Reeves. Whenever I hear it I have to stop whatever I'm doing to listen to it.

Posted by: jake and millie | December 15, 2006 4:01 PM | Report abuse

Great lists, folks; oh so sad and yet so beautiful. I'd like to add the saddest German song ever:

Lili Marleen - Marlene Dietrich/ Lale Andersen

Posted by: Anonymous | December 15, 2006 4:06 PM | Report abuse

Whoever said Tom Waits is absolutely right, about every song they mentioned, he kind of has the market on sad songs.

But I've neglected The Mountain Goats, their music is largely sad, sad and disturbing.

Emmie, I missed the Pogues at the 9:30 last year. Hopefully they'll come back through soon.

Posted by: The Ocho | December 15, 2006 4:08 PM | Report abuse

Halleujah, the cover by Jeff Buckley, I think. Makes me weep.

When I was little I cried everytime I heard Doggie and the Butterfly by Heart.

Posted by: JMDC | December 15, 2006 4:09 PM | Report abuse

Death by cancer, indierock style:

Casimir Pulaski Day- Sufjan Stevens

Posted by: Chris K | December 15, 2006 4:12 PM | Report abuse

"Did She Mention my Name" Gordon Lightfoot
I know I am really old but "The Baggage Coach Ahead" and "Two Babes in the Woods"; and the little girl selling matches but burned them all up trying to keep warm. What's up with singing those songs to kids? We loved them though.

Yes! for "Angel from Montgomery", "Hello in There", "I'm So Lonesome, I Could Cry"
Another of Hank Williams good for crying is "Weary Blues"

Posted by: Anonymous | December 15, 2006 4:15 PM | Report abuse

Lightning Crashes by Live makes me cry. It is worse since I had my daughter.

Posted by: So sad | December 15, 2006 4:18 PM | Report abuse

Pearl Jam: Black
Pearl Jam: Army Reserve
Radiohead: Street Spirit
Ben Harper: Another Lonely Day

Posted by: ErFigone | December 15, 2006 4:20 PM | Report abuse

Nameless One: about 45 minutes after I posted, I realized my mistake, and laffed my ass off! Miss Helen would also think this is funny (shout out to my home skillet, sweet dreams and flying machines and everything else). FYI, we bawled, we're not that kind of friends.
TSH, bringing the Freedy! Love Freedy Johnston, Home Again is the saddest song I can remember from 199?. Perhaps 1996?

Posted by: miss belle | December 15, 2006 4:22 PM | Report abuse

Strange Fruit -- Billie Holliday

Posted by: tarheelgal | December 15, 2006 4:25 PM | Report abuse

umm...mason patriot i think has the exact same "heartbroken" playlist for his ipod...every single one he suggested...but add "you could be happy" and "chasing cars" by snow patrol in addition to "run"

Posted by: amatulips | December 15, 2006 4:25 PM | Report abuse

Whelp ... seein's how I am preparin' a little iTunes Christmas gift to the man who broke my heart .. how's these??

"Leave" - Matchbox 20
"Two Days in February" - Goo Goo Dolls
"Over My Head" - The Fray
"Holy Mother" - Eric Clapton
"Out of this World" - Bush
**Cheese Factor Alert*** - "I'm not in Love" - 10cc
"Dusk & Summer" - Dashboard Confessional
"It Doesn't Matter" - Alison Krauss .. actually any thing she does .. she's country's Sarah McLachlan
"But Not For Me" - Sarah Vaughn

As stand-alone sad songs...
"Vera" - Pink Floyd
"The River Runs Low" - Bruce Hornsby & The Range
"Waiting" - The Devlins
"One of These Days" - Tim McGraw
(Yikes .. High School Memory/High Cheese Factor here ....) - "I Won't Hold You Back" - Toto

Okay .. I have tortured you enough with my crap musical tastes!

Posted by: Wil In Minneapolis | December 15, 2006 4:33 PM | Report abuse

"society's child," janis ian
"no one is to blame," howard jones
"knockin' on heaven's door," warren zevon (and only warren zevon)
"nothing man," bruce springsteen
"so far away," carole king
"so far away," dire straits (yeah, i was in a long-distance relationship once)
"am i welcome here?" eric lane barnes
"happy christmas (war is over)," john lennon
"asleep," the smiths

Posted by: bamagirlinVA | December 15, 2006 4:35 PM | Report abuse

"I'm on Fire" by Springsteen!

Posted by: Team Weingarten | December 15, 2006 4:43 PM | Report abuse

How the Hell could I neglect Miss Patsy Cline!! ... "She's Got You"

And Bamagirl in VA ... check out "Far Away" by Nickelback .. if you like Carole King and Dire Straits .. you might like this one too.

Posted by: Wil In Minneapolis | December 15, 2006 4:44 PM | Report abuse

Lee Greenwood's God Bless the USA
Neil Diamond's Heartlight (ET anyone?)

Posted by: WDC | December 15, 2006 4:45 PM | Report abuse

As sad as the backstory for Tears in Heaven is that for:
Led Zeppelin, All my Love

Maybe it's just because I have a young son I cherish, but those songs make me both terribly sad but also appreciate my life and good fortune .

Posted by: 4Dillon | December 15, 2006 4:51 PM | Report abuse

Is it wrong that I just literally laughed out loud when I read "Taps"

Hahaha I'm still laughing. Sorry.

Posted by: not bluto | December 15, 2006 5:01 PM | Report abuse

How could I forget -- even endless airplay can't blot the depressing images (can't stand hearing it on the radio in the morn) Everclear's "Father of Mine" Something about the line: "Never had the joy of a welfare christmas" Sigh!

Posted by: dornish sand | December 15, 2006 5:03 PM | Report abuse

Led Zep - "That's the Way"

Miles Davis - "Flamenco Sketches"

Pink Floyd - "Us and Them" and "Wish You Were Here"

The Doors - "Hyacinth House"

Prince - "Purple Rain" (and for some reason my brother picked that as his wedding song...aaaand divorced his wife a few years later...)

Posted by: now i'm depressed... | December 15, 2006 5:08 PM | Report abuse

Gotta have
Steely Dan "Any world that I'm welcome to"
Supertramp "Is it mine"

IMO some entries are confusing sad with emotional (which has larger scope).

Posted by: jk | December 15, 2006 5:18 PM | Report abuse

Michael Andrews and 'Mad World' is one of my newest sad ones. But when you have just had your heart broken lots of songs sound sad. When you are happy they are just fun to sing along to--like 'creep', by radiohead.

Posted by: Anonymous | December 15, 2006 5:32 PM | Report abuse

"Teenangel" always makes me cry.

Posted by: Anonymous | December 15, 2006 5:33 PM | Report abuse

The question was ... What songs make your eyes go all misty or get you in a wistful mood? There is nothing that says we can't comment on emotional songs as well. Wistful means "full of yearning or desire tinged with melancholy" .. Misty means "tearful" .. tears don't always come with sadness .. sometimes they come with other emotions. Right?

Posted by: Anonymous | December 15, 2006 5:40 PM | Report abuse

Gets me EVERY time:

Strange Fruit by Billie Holiday

Posted by: CJB | December 15, 2006 5:47 PM | Report abuse

Safe and Sound by Sheryl Crow
Long Road by Pearl Jam
Ghost by the Indigo Girls

God, this discussion could go on forever, couldn't it??

Posted by: Doonesburied | December 15, 2006 6:33 PM | Report abuse

When my father in law was in intensive care we would bolster ourselves by listening to Andrea Bocelli's Canto de la Tierra, after he passed away it has become the most sad song to my wife and me. Invariably we hear it when we go into an italian restaurant and it breaks us up...

tw mentioned Tom Waits- (wait a minute is tw Tom Waits?)- Tom gets me too with his new cd set, disc 2 is aptly named bawlers.

Marfa by Salif Keita
Who knows where the time goes by Sandy Denny
One for my baby by Sinatra
sad songs all

Posted by: grubster | December 15, 2006 6:47 PM | Report abuse

Of course there is opera.
How about a father saying goodbye to his favorite daughter, knowing if he doesn't banish her, the world will end? That's "Die Walkure",
and also the end of "Otello" when he asks for one more kiss from the beloved wife he just murdered.
"Vesti Il Gubbio" about a clown who has to dress up and perform every night, knowing his younger wife is cheating on him.
And Carmen, when he loves her, but hates himself.
Trust me, get a Placido Domingo CD and listen!!! (please forgive any typos!)

Posted by: Barb | December 15, 2006 7:36 PM | Report abuse

Sanvean by Lisa Gerrard
Hymn for the Fallen by Dead Can Dance
Love will Tear Us Apart by Joy Division
Come Back to Me by X (song about Exene's sister's death)

Posted by: Lisa | December 15, 2006 8:25 PM | Report abuse

Would you believe Carpenters' TOP OF THE WORLD? Once had to pull of the road in tears when it came on the radio. How about BRIDGE OVER TROUBLED WATER or Trisha Yearwood's THE SONG REMEMBERS WHEN, which seems to be an anthem, but's actually full of regret? Same for ME & BOBBY McGEE.

Posted by: DEGATESJR | December 15, 2006 8:25 PM | Report abuse

"Yellow Coat" by Steve Goodman

Remember all the mornings
We'd walk around the park
The nights we babysat for Billy's kids
And all the times we used to talk
Of having one ourselves
I don't remember why we never did

"Mr. Bojangles" by almost anybody

He danced for those in minstrel shows
And county fairs
Throughout the south
He spoke with tears of fifteen years
How his dog and him traveled about
His dog up and died, he up and died
After twenty years he still grieves

Very different songs and they both tear me up.

Posted by: WesternShore | December 15, 2006 8:50 PM | Report abuse

Damien Rice's "Delicate."

"And why'd you fill my sorrow
With the words you've borrowed
From the only place that you've known
Why'd you sing Hallelujah
If it means nothing to you
Why'd you sing with me at all?"

I never liked "China" by Tori Amos until after heartache.

Alot of Fleetwood Mac songs, especially "Silver Springs".

Posted by: t | December 15, 2006 9:53 PM | Report abuse

Some of you people have very strange readings of Springsteen songs. Thunder Road? Yikes!

I didn't see any Jackson Browne. These Days is a perfect song about clinical depression. Odd to say that it's the highlight of Greg Allman's solo career.

I would also add Neil Young's Tonight's the Night -- the whole album.

Posted by: Mark | December 16, 2006 8:37 AM | Report abuse

NJ and TW beat me to the punch with their shout-outs to Bob Dylan's "If You See Her, Say Hello" and Tom Waits' "Martha," respectively.

I don't think anyone has mentioned these, but there's so much text to sift through that I may have missed it. With the hope of originality and the perception that no one has mentioned Dave Matthews, I offer the following:

Dave Matthews, "Stay or Leave"
Dave Matthews Band, "Grace Is Gone"
Dave Matthews, "Gravedigger"
Dave Matthews Band, "I'll Back You Up"
Dave Matthews Band, "Halloween"
Don't know who originally did "Long Black Veil" - I heard DMB's version first and then Johnny Cash. Either way, dang.
Ben Folds, "Carrying Cathy"
Ben Folds Five, "Selfless, Cold and Composed"
Dire Straits, "Romeo and Juliet"
"There's a Fine, Fine Line" from Avenue Q
Virtually anything and everything by PJ Harvey
Rascal Flatts, "What Hurts the Most"
Rolling Stones, "Angie"
Beatles, "The Long and Winding Road"
"Angel from Montgomery" - don't know who did the original
Damien Rice - O, the entire album. I bought it and can't listen to it.
David Gray - most of White Ladder, but especially "Say Hello and Wave Goodbye"
Rod Stewart, "The First Cut Is the Deepest"
Rascal Flatts, "My Wish." I didn't know the name of this song and started crying just reading the lyrics I had googled. Also especially poignant having moved recently, far away from friends and family.
Carbon Leaf, "Changeless." Ripped me up to hear it as I moved. ("What are the odds, what are the odds this ends and we don't meet again? What are the odds, what are the odds that I will miss your smile?")
"Tell Laura I Love Her" - can't remember the artist
Jeff Carson, "The Car"
Guster, "Rocketship"
Guster, "Medicine"

Posted by: musicgeek | December 16, 2006 11:48 AM | Report abuse

Ugh...I did NOT want to participate in this list, but last night I attended the memorial service of a dear friend that committed suicide and her family played this song, which is going to haunt me FOREVER.

"The Wind Knows My Name" - Fairground Attraction

Posted by: Alison | December 16, 2006 12:45 PM | Report abuse

"Hallelujah" by Leonard Cohen but there are soo many cover versions...and "American Pie" by Don McLean...and "Wenn sie diesen Tango tanzt" ("When she dances this tango") by Pur

Posted by: Bille | December 16, 2006 3:54 PM | Report abuse

Not Bluto, I am curious. Why would Taps be funny. I grew up mostly on army bases so don't get the joke. Am I old AND out of touch? Guess so.

Posted by: Dona Dunsmore | December 16, 2006 4:19 PM | Report abuse

I see, this list is really for a different sort of sad song.

Posted by: Dona Dunsmore | December 16, 2006 4:20 PM | Report abuse

Grateful Dead, He's Gone. Jerry says goodbye to Pig Pen.

Bob Dylan, Tangled Up in Blue.

Silent Night, by whomever. It was playing while we decorated the tree when the police came to our door to tell us my brother was killed in an accident on his way home from college in 1982. 25 years later it tears me apart whenever I hear it. Tim probably laughs at me ever time, "What, you wanted 'Grandpa Got Runover By a Reindeer'?".

25 years. 25 effin years.

Posted by: I'm Don, and I'm an Alcoholic.... | December 16, 2006 5:14 PM | Report abuse

What a nice holiday season theme. Finally.

Townes Van Zandt: Tecumseh Valley; Nothin'; Pancho and Lefty.

John Hiatt: If I Could Love Somebody (Esp Marti Jones' version).

Paul Cebar & The Milwaukeeans: Somewhere We Both Belong.

Seldom Scene: Darlin' Corey.

Posted by: Rabid Rabbit | December 16, 2006 5:38 PM | Report abuse

Pancho and Lefty! Great call!

Posted by: Mark | December 16, 2006 5:57 PM | Report abuse

Edelweiss, Sound of Music soundtrack
Happy Christmas, John Lennon
Imagine, John Lennon
Beautiful Boy, John Lennon
What a Wonderful World, Louis Armstrong

Posted by: Jom | December 16, 2006 10:19 PM | Report abuse

In the spirit of the season, I recommend John Cale's version of Blue Christmas. Beyond sad, close to suicidal. Although, can a song be sad and also tongue-in-cheek?

Posted by: Benny Boy | December 17, 2006 2:11 AM | Report abuse

Blue in Green. Miles Davis.

Posted by: Ern | December 17, 2006 11:39 PM | Report abuse

And-->Bulletproof...I wish I was. Radiohead.

Posted by: Ern | December 18, 2006 12:04 AM | Report abuse

The Clash, "Broadway".

Posted by: Avon-on-Thames | December 18, 2006 8:44 AM | Report abuse

Signed D.C. by Love

Posted by: London | December 18, 2006 8:58 AM | Report abuse

What about "F--- and Run" by Liz Phair? That song gets me every time.

Posted by: Mr Ecks | December 18, 2006 10:06 AM | Report abuse

How no one has mentioned this I don't know..
Sounds of Silence by Simon & Garfunkel

Also, Mad World by Gary Jules (cover of Tears for Fears)

Posted by: Tiff in the OK | December 18, 2006 10:35 AM | Report abuse

In college I majored in Suicide Rock. I am also from Texas so I have the whole miserable c&w angle covered as well. My choices:

(1) I can't help it if I'm still in love with you - Hank Sr. and many others
(2) Long, long time - Jerry Jeff Walker
(3) Pancho and Lefty - Willie and Waylon
(4) He stopped loving her today - George Jones
(5) Anything that ever came out of Patsy Cline's mouth

(1) Break your heart - Bare Naked Ladies, also Brian Wilson
(2) Wouldn't it be nice - Beach Boys. Upbeat pace, deadly lyrics.
(3) Mona Lisas and Mad Hatters - Elton John
(4) Cathedrals - Jump Little Children
(5) I'm so happy (I can't stop crying) - Sting

Bob Dylan section:
(1) Don't think twice, it's alright
(2) Just like a woman
(3) Bob Dylan's Blues
(4) Queen Jane Approximately
I could go on and on like this.

And a few seasonal picks:
(1) River - Joni Mitchell
(2) Same old Auld Lang Syne
(3) Brick - Ben Folds Five
(4) Theme from Charlie Brown's Christmas

This is painful, but fun, like picking at a hangnail!
Just a taste

Posted by: Anonymous | December 18, 2006 11:01 AM | Report abuse

River (Robert Downey Jr's version)
The Night Before Life Goes On (Carrie Underwood)
Everything Tom Waits ever did
When I Look to the Sky (Train)
Catalyst by Anna Nalick

Posted by: Dupont | December 18, 2006 12:43 PM | Report abuse

Again - Janet Jackson
Something I can Never Have - NIN
All I Want is You - U2 (Gets me every time I watch Reality Bites)

Posted by: CB | December 18, 2006 12:55 PM | Report abuse

will second (third? fourth?) these:

jimmy eat world, "23"
radiohead, "bulletproof (i wish i was)"
death cab for cutie, "i will follow you into the dark" - i actually cannot listen to this in the car or i will crash from bawling.

will add these if no one's already said them:
ani difranco, "so what"
ani difranco, "school night"
simon & garfunkel, "overs"
the beatles, "julia" - few things sadder than john lennon singing an ode to his dead mother.

i used to consider queen's "bohemian rhapsody" a funny song until i found out what it was about. after that i still love it but sometimes it's just unbearably sad.

Posted by: firehat | December 18, 2006 1:31 PM | Report abuse

"I Know You By Heart" - Eva Cassidy. Can't listen to it around anyone, it's just too embarrassing. Her version of "Over the Rainbow" is a very close second.

"Angel" - Sarah McLachlan

"Coat of Many Colors" - Dolly Parton (she can kill you, and I don't mean with those boobs, either)

Posted by: ek | December 18, 2006 3:27 PM | Report abuse

For God's sake, no Elliot Smith!???

Posted by: JM | December 18, 2006 5:55 PM | Report abuse

Macy Gray -- I Try
Annie Lennox remake of Bob Marley -- Waiting In Vain

Posted by: Allison | December 18, 2006 6:26 PM | Report abuse

This compilation seems to beg for another playslist - best breakup songs - which is another blog post altogether. Up for it, Liz?

Posted by: musicgeek | December 18, 2006 11:43 PM | Report abuse

It isn't pop but "I'll be home for Christmas" always reminds me of the kids in the armed forces. More so these last few years

Posted by: casper51 | December 19, 2006 8:25 AM | Report abuse

How about a list of songs that get you fired up? I'm itching to submit some Gil-Scott Heron.

C'mon Liz. I've got $5 making a hole in my pocket, it's yours if'n you grant my request. Perhaps name a cat after you. Your call.

Posted by: St. Nick | December 19, 2006 8:39 AM | Report abuse

The Dirty Three- "I remember a time when you used to love me" (They opened for Sonic Youth back at a concert I went to and this song stopped me dead in my tracks and I became so wrapped up in the intensity I literally began to cry. There are no words but man, this guy's heart BLEEDS on this song through his violin)

Me'Shell NdegeOcello- "Fool of Me"

Tori Amos- "Hey Jupiter (The Dakota Version)" (I go from time to time.
I know where the cupboards are.
I know where the car is parked.
I know he isn't you. Nothing is.)

Smashing Pumpkins- "Soma" (So let the sadness come again.
On that you can depend on me
Until the bitter, bitter end
When good sleeps in bliss)

Something Corporate- "Walking By" (sooo good!) (Why do you look when you've already found me?
What did you find that could leave you walking by?)

Ben Harper- "Walk Away" (my official break up song)

Dire Straits- "Romeo and Juliet"

Mariah Carey- "Without You"

Ben Fods Five- "Brick"

Ani DiFranco- "Both Hands"

Oh man, I could go on all day with this one...

Posted by: Anonymous | December 19, 2006 10:51 AM | Report abuse

Oops, almost forgot... as supplement to my list above,

Barenaked Ladies- What a Good Boy (I found this AMAZING college accapella version on the internet once that just blew me away- made the song absolutely beautiful).

Posted by: he broke my heart | December 19, 2006 10:56 AM | Report abuse

When I was drinking - Hem
Once in a While - M. Peyroux
You're Gonna Make Me Lonesome. - M. Peyroux
Handbags & Gladrags - Rod Stewart
A Minor Incident - Badly Drawn Boy
Knot Comes Loose - my morning jacket

Posted by: fulltilt | December 19, 2006 12:37 PM | Report abuse

What? no Gloomy Sunday?

Posted by: northzax | December 19, 2006 6:37 PM | Report abuse

X, 4th of July

Posted by: Anonymous | December 20, 2006 12:47 PM | Report abuse

"Last Kiss" by Pearl Jam
"Tears in Heaven" by Eric Clapton

They were already sad, but took on extra meaning after we lost our 5 week old daughter to a rare and undiagnosed congenital heart condition. I cry every time I hear these songs, probably will the rest of my life.

Posted by: carusocm | December 20, 2006 6:44 PM | Report abuse

Ain't No Sunshine When She's Gone by Bill Withers

Posted by: Brucie | January 3, 2007 10:43 PM | Report abuse

I agree.

Garth Brooks: The Dance
and an old Irish song, Willie McBride

Posted by: Amanda | January 10, 2007 9:07 PM | Report abuse

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