What's the saddest song on your playlist?

I’m not much of a cryer, but these two songs really make it raw for me:

Cheryl Wheeler’s song “Since You’ve Been Gone” she wrote after the death of her father is just crushing in its realness.
I got married two months ago and used this song (Beth Hart “Mama This One’s For You”) for the mother/son dance. My husband’s mother passed away last year, so he danced with his sisters for the song. I still can’t get through this song without tearing up. It’s not a sad song, but it’s gutting nonetheless.

“She Was Too Good To Me”, Chet Baker

Slight nitpick - it’s not a *song *if there’s no singing.

People who don’t know any other word for a musical piece use “song” for everything musical. Besides, there are these.

And if we’re gonna start listing sad (or wistful) Chopin pieces, we’ll be here all night.

Every time Look Left’s Lighthouse comes up on my ipod, I have a choice to make. Skip it, or have a good cry. Gets me every time.

It’s a tie for me: Assemblage 23’s 30KFT (Assemblage 23 - 30kft - YouTube) and C. W. McCall’s Roses for Mama (Roses For Mama - C.W. McCall (1978) - YouTube).

(Sorry, linking properly on my iPad is a pain.)

The latter is the sappiest song in the known universe (I like McCall and it’s on an album) but I can’t listen to it without blubbering, so I don’t. I always skip it.

A year ago we sandbagged our house and waited for the tide to turn and the rain to stop. Our house was ok but our neighbours lost theirs. A few days later my son sent me a link to Rachael Dadd’s song Our Arms - Rachael Dadd - Our Arms (Official Audio) - YouTube
I am undone by it every time.
‘You take the stairs three at a time and you are first to reach the baby…’

MiM

Very true, my friend. I could add:

I would add Tomaso Albinoni Adagio in G

My daughter and I were at a beautiful outdoor wedding, and after, the first dance was ‘Harvest Moon’ by Neil Young, and the two of us were sitting there with tears streaming down our faces. I can’t say why, really. It’s one of her dad’s (and my husband’s) favorites, and we are both at the age when fathers and husbands pass on from strokes, heart attacks. Like, time is running out…

What is that melancholy, slow, sad song by U2? It’s not one of the older songs, it’s not ‘One’ (though very similar). That one. I could hear it in passing walking down the street on my way to the post office, and I would burst into tears.

Fair enough. The most wistful song with words on my playlist is Ave Maria. I prefer Liszt’s straight piano arrangement, but having no words, it’s not technically a song. :slight_smile:

Chet Atins: Shubert’s Ave Maria

Very nice! Wish they didn’t add the backing strings, though. That, to me, kinda gives it a Muzak vibe.

“Chelsea” by Counting Crows.

I’ve said before that Adam Duritz is the most depressing son of a bitch on the face of the Earth. Johnny Cash would have told him to lighten up. But with such lines as

and

and

At the end of that last quote, he just keeps singing “I keep hoping…I keep hoping…I keep hoping.”

I always felt he nailed it with:

It’s 4:30 A.M. on a Tuesday
It doesn’t get much worse than this
Tuesdays are the worst, and 4:30 means you’re awake at an ungodly hour and you have a whole Tuesday stretched out before you.

Barber’s Adagio Adagio for Strings (Samuel Barber) - YouTube (kind of funny as this link is hosted by a depression treatment center!)

Second Hurt, although my favorite version is on NIN Beside You In Time DVD

One other–Trampled Rose, as performed by Tom Waits himself, or Alison Krause on Raising Sand.

Normally, I’d agree with you. But I work second shift, so I’m usually just going to bed at 430am.

There’s a line in “High Life” where he really gets me. It’s when he sings “waiting for trains that just never come.”

The Band Played Waltzing Matilda makes me feel a bit sad. So do a few Colombian vallenatos like Jaime Molina or El Sentido.

Which pairs well with Tom Waits’ “The House Where Nobody Lives.”

But I can’t listen to Waits’ “Georgia Lee” without full-on leakage. Cuts a little to close to the bone.

Joni Mitchell, Song for Sharon

A woman I knew just drowned herself
The well was deep and muddy
She was just shaking off futility
Or punishing somebody
My friends were calling up all day yesterday
All emotions and abstractions
It seems we all live so close to that line
And so far from satisfaction

:frowning:

What? No Richard Thompson songs yet? RT is the definition of doom and gloom.

I can’t say that I actually have play lists, but I’m a long time RT fan and could throw out a few suggestions:

“Withered and Died” (with Linda Thompson)
“She Cut Off Her Long Silken Hair”
“1952 Vincent Black Lightning”
“Has He Got A Friend For Me?” (with Linda Thompson)

Heck, it’s hardly any fun if we’re allowed to pick RT songs.