Gorgeous Melancholy, I Love You (Sad Songs Write-Off)

Aug 08 '05    Write an essay on this topic.


The Bottom Line Go pick up some underplayed folkies & cry your heart out.

I saw this write-off started by alexdg1 and couldn’t help think it was perfect for me. Given my penchant for modern singer-songwriters & folk music, it is inevitable that I end up listening to a lot of sad songs. I love them, I can’t help it. There is nothing better than a good cry. So I had a really hard time narrowing this down. Some of my favorite “sad songs” follow – ones that are guaranteed to make me stay in the car to hear the end, or curl up under the covers crying. Am I crazy to enjoy that? Perhaps. Now you can enjoy it too…

Rose Polenzani: Olga (Dragersville – Damon Records, 1999)

Well, ever since I've fallen under Jesus,
I feel so closed up,
and my heart, it aches for Mariana,
and I miss her, I miss her.
Sometimes I see her in the marketplace,
and I cry out,
and they hold me down.
They think I've seen the savior's face,
but it's only that I'm lonely.


This was the song that made Rose an indie-folk “hit”, although that means considerably less when you’re talking about an audience in the dozens. Still, this little story about a girl who fell in love with another girl and is forced to marry a boy in order to “come to Jesus” and be redeemed is incredibly sad. It has almost a folk-tale feel about it, and Rose’s haunting voice adds to the power and fear of Olga.

Jennifer Kimball: This is My New Vow (Veering From the Wave – Imaginary Road, 1998)

Walk back down the aisle -
No cameras, no flowers this time.
You will find your way back home, no one at your side.
Only absence will be your lover, regret your bride.
And this is my new vow
not to have you or hold you
no more my arms enfold you
from this day on.


Because I am a glutton for punishment (or something), I listened to this song quite a bit in the weeks before my wedding. It is all about the gut-wrenching process of divorce told from the perspective of a woman who has major regrets but knows she is doing the right thing. She goes through the happy memories (“swimming in the azure blue”), and the good intentions (“we have lived and partly lived not to let this happen”) to try and figure out how they arrived here. This song is played entirely on strumstick, which gives it a spare, melancholy feel. If you need a good cry at the end of a relationship, this is definitely a good one.

Patty Griffin: Not Alone (Living With Ghosts – A&M Records, 1996)

One of them bullets went straight for the jugular vein
There were people running , a flash of light
Then everything changed
Nothing really matters in the end you know
All the worries sever
Don't be afraid for me my friend
one day we all fall down forever

The wedding date was June just like any other bride
She loved him like no one before
and it was good to be alive
But sometimes that can slip away as fast
As any fingers through your hands
So you let time forgive the past
and go and make some other plans


No list of sad songs is complete without something from the queen of melancholy, Patty Griffin. It was very difficult to pick out just one of her songs, but this one from her first album won out. Mostly because I didn’t start listening to this album until just before 9/11, and after that day, I couldn’t stop listening to this song over and over. Some young man traumatized, who has the love of his life but can’t quite reach her, who experiences incredible tragedy through illness & death. I couldn’t stop thinking about all those people who died horrible deaths, who “fell down forever.” And yet, there is something very comforting about this song – that there is a common experience that can be gleaned out of tragedy.

Natalie Merchant: Beloved Wife (Tigerlily - Elektra, 1995)

you were the love
for certain of my life
you were simply my beloved wife
I don't know for certain
how I'll live my life
now alone without my beloved wife
my beloved wife

I can't believe
I've lost the very best of me


A very simple love song from a man to his deceased wife. You hear stories about elderly married couples where one dies, and the other dies a few days later. Why? The doctors can only guess that the spouse really did die of a broken heart. To me, that is touching, so sad, and beautiful. This song seems to describe that very situation – you can’t imagine that the narrator will be holding on much longer.

Holly Cole (orig. by Patty Larkin): I Told Him My Dog Wouldn’t Run (Dark Dear Heart - Blue Note Records, 1997)

He was laughing but I didn't get the joke
He was dying to light up a smoke
And I wanted to cry
In the florescent light of the restaurant
I smiled and I got up to go
I was hoping for a goodbye to hold
But it was kinda like touching a ghost
So I ran when I walked out


Although this is originally a Patty Larkin song, I find the Holly Cole version so much more heartbreaking. It relays the story of a woman who goes to meet up with an old, very dear friend, who has become completely wrapped up in fear and anxiety (He said, “I read the Bible every day to try to keep the demons at bay. Thank God when the sun goes down I don’t blow away.”) I listened to this song endlessly after my boyfriend and I broke up over religious differences and CRIED. (He is now my husband, so obviously we worked that out.) The care that the narrator has for her friend (that she asked to marry at one point) is evident, and watching him spin himself into a little cocoon is incredibly sad. Holly Cole has a knack for spinning out heartrending & melancholy tunes – her voice is so beautiful, it just lets this one shine right through.

Jeff Buckley: Last Goodbye (Grace - Sony, 1994)

Did you say, ‘No this can’t happen to me?’
Did you rush to the phone to call?
Was there a voice of some kind in the back of your mind, saying maybe, you didn’t know him at all?
You didn’t know him at all…you didn’t know.

Well, the bells out in the church tower chime
Burning clues into this heart of mine
Thinking so hard on her soft eyes and the memories
Offer signs that it’s over... it’s over


My only male entry here was a no-brainer. This is the ultimate break-up / death / loss song. The guitar build is phenomenal, the lyrics are gorgeous, and Buckley’s voice is, as always, haunting. Add to that the fact that Jeff Buckley died a tragic death at age 30, getting swept away by a Mississippi River undertow and drowning in 1997, this song is the definition of Sad Song.

Ani Difranco: Hello Birmingham (To The Teeth - Righteous Babe Records, 1999)

And the blood poured off the pulpit
The blood poured off the picket line
Yeah, the hatred was immediate
And the vengeance was divine
So they went and stuff god
Down the barrel of a gun
And after him
They stuffed his only son

Hello birmingham
It’s buffalo
I heard you had some trouble
Down there again
And I’m just calling to let you know
That somebody understands


It has been a few years since Ani has really moved me, but this entire album was absolutely beautiful. Pouring sadness and regret and anger out in every track, To the Teeth culminated for me in this ode to Birmingham, Alabama from Ani’s hometown of Buffalo. Ani compares the respective history of racial violence in Birmingham with the recent shooting of Dr. Slepian, a Buffalo doctor who performed abortions. The lyrics are all at once tender and furious…Ani’s anger comes through each soft note with ferocity.

Tori Amos: Tear in Your Hand (Little Earthquakes – Atlantic, 1992)

all the world is
all i am
the black of the blackest ocean
and that tear in your hand
all the world is DANGLIN'...
danglin'... danglin' for me DARLIN'
you don't know the power that you have
with that tear in your hand
that tear in your hand

maybe i ain't used to maybes
smashing in a cold room
cutting my hands up
every time i touch you
maybe maybe it's time
to wave goodbye now
time to wave goodbye now


Oh, Tori, how I have loved you. I received this album on my 16th birthday and immediately gravitated towards this song even before I really listened to the lyrics. But when you are a teenager and your heart is getting broken, Tori’s descriptive words combined with killer piano are exactly the thing. This song has just the right touch of orchestral background & slow sadness to make the list. It’s another that I’ve put on ‘repeat’ for hours on end…

Honorable Mention
Ben Folds: Carrying Cathy
Jonatha Brooke: West Point
U2: Bad
Joni Mitchell: Both Sides Now

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