top 100 saddest songs of all time

"It Never Entered My Mind" - Rodgers/Hart
"You're A Big Girl Now" - Bob Dylan
"So Long" - Rickie Lee Jones

Michelle Shocked - "Stillborn"

Since I just finished the 33 1/3 book on Swordfishtrombone:

Tom Waits - "Soldier's Things"
"And this one is for bravery
And this one is for me
And everything's a dollar in this box"

"How I Long to Feel that Summer" - Gorky's Zygotic Mynci

EMO, I know, but even when I was IN that summer this song felt sad and nostalgic.

Roads - Portishead
All Things to All Men - Cinematic Orchestra and Roots Manuva

"Smalltown Boy", The Bronski Beat

to broadly echo stuff from immediately upthread, so much of mark koz's or ricki lee's catalog brings on the sad

62. "Against All Odds" by Phil Collins -- Fuck you. It's the best song he ever pulled out of his ass. And it's a great, soppy, tear-jerker.

yeah. why this one works, i don't pretend to understand. but, it does, against all odds, even.

"Teddy Bear" - Red Sovine
*sniffle*

http://www.youtube.com/watch?v=06MfMaxp8RU

Well you better believe I took my turn at riding Teddy Bear

*stifles a laff*

Gnossienne No. 5, Modéré

i think we need to re-do this because nobody mentioned "halah" by mazzy star, which i can't listen to without crying (esp the line "you're leaving before my time").

I have the same experience with Hope Sandoval's "Down the Steps", a portrait of someone who's in denial after the death of a friend. there's something very convincing in the way she avoids using the word "death" or any of its synonyms, slips confusedly between past and present tense, and mixes matter-of-fact observations about the body with incoherent musings about where the soul has gone. her quavering, uncertain delivery of the last line ("wake up, make us some tea") is just devastating.

that is a great one too. she is easily one of my favorite singers of all time. her voice is just so beautiful, clear and youthful yet darkened always by this palpable weight of despair, like she could just break down and start crying any second.

Man of the World - Fleetwood Mac (Peter Green iteration)

14, Fleetwood Mac - Man Of The World
― eyesteel (eyesteel), Friday, June 2, 2006 7:43 AM (7 years ago) Bookmark Flag Post Permalink

Oops! Sorry, eyesteel

Any number of versions of Adagio for Strings -- hell, it even works "for horns":
https://www.youtube.com/watch?v=6fYNlsRHSXo

Stephin Merritt and two of his 69LS allies did a 'saddest songs' show in 2000:

I'm Forever Blowing Bubbles [Kenbrovin/Kellette]
Seasons in the Sun [Brell/McKuen]
I Live off You [X-Ray Spex]
He Hit Me (It Felt Like a Kiss) [Goffin/King]
My Man [Yvain/Willmetz/Charles/Pollock]
The Winner Takes It All [Abba]
Big Red Balloon [Lee Hazelwood]
Anywhere (Like the Moon) [Kid Montana]
The Silver Swan [based on a 16th century madrigal by Orlando Gibbons]Oh, Danny Boy [trad. Irish]
If You Go Away [Brell/McKuen]
Pretty in Pink [The Psychedelic Furs]
Maria, Maria [Merritt]
Some Small Hope [Astley/Sakamoto]
Don't Get Around Much Anymore [Duke Ellington]
In My Room [Pocktiss/Vance]
Measure of a Man [ld beghtol]
The Slave's Lament [Robert Burns]
Big Louise [Scott Walker]
An Hour Too Late - 1890s parlour ballad
As Soon As I Hang up the Phone [Conway Twitty]
The Butcher Boy [trad. Irish]
Send in the Clowns [Stephen Sondheim]
'Tis the Last Rose of Summer [trad. Irish; lyrics by Sir Thomas More] - Is That All There Is? [Leiber/Stoller; extra lyrics by Christina]

which allies? was it LG Benghtol and Lemony Snicket? sounds awesome regardless.

Is broken hearted same as sad?

Cat Power - Still In Love
Palace - New Partner

it is. for cat power, my pick would be "maybe not".

Treeship, it was LD & Dudley Klute. (w/ SM, The Three Terrors)

that is a great one too. she is easily one of my favorite singers of all time. her voice is just so beautiful, clear and youthful yet darkened always by this palpable weight of despair, like she could just break down and start crying any second.

― Treeship, Wednesday, June 19, 2013 12:39 AM (Yesterday)

hmm, I don't really get an "on the verge of a breakdown" feeling from her music, apart from "On the Steps" and a few of the quieter Mazzy Star songs ("Look on Down From the Bridge"?). if anything it sounds like she could fall asleep any second, and the constant, low-level moodiness is perfect for when you're feeling tired and depressed but aren't in the mood for anything properly weepy.

when i imagine the breakdown, it is like she is on the verge of quietly walking out of the studio and driving calmly back to her apartment and lying in bed lightly but ambivalently crying.

but i agree, there is a numbness there, which is familiar to anyone who has experienced really significant depression for a prolonged period of time. she sounds like she is suffering to me, i guess. but i still enjoy listening to the music and find it very beautiful.

well she does have a habit of quietly walking offstage in the middle of concerts, so you may have a point there (I kid). I've listened to her solo stuff so often while falling asleep that it's hard for me to hear it as anything but chill-out music — it's like I've conditioned myself to tune out the content/lyrics/emotions in favor of the vibes, maaaan. the same thing happens when I listen to certain music regularly while exercising. using music for purely functional purposes has its drawbacks.

oddly I don't like most of Mazzy Star's stuff, especially when they're in retro-psych mode, and I don't like Opal's heavier material (on Happy Nightmare Baby). Rain Parade completely bores me. sorry, Dave Roback, but I don't think I like you.

Man, Taking Tiger Mountain brings the tears every time. Every time! And I'm mostly unemotional? Sort of?

No xpost

Carol - "So Low"

"Flooding" by Kristin Hersh, the piano demo.

"In This Hole" - Cat Power
"Holding" - Grouper
"For Martha" - the Smashing Pumpkins
"My New Freedom" - Elliott Smith
"Something in the Way" - Nirvana
"The End of the Rainbow" - Richard & Linda Thompson
"Sawdust & Diamonds" - Joanna Newsom
"God" - John Lennon
"This Night Has Opened My Eyes" - The Smiths
"Buzz Saw" - Xiu Xiu

People have some odd ideas on what constitutes a sad song.

A harder challenge would be coming up with some sadder than any of the songs on Mount Eerie's A Crow Looked at Me.

Yeah :-(

I mean, Phil abandons/dismisses any attempt at making "art" on that record, because it's been rendered completely meaningless and useless to him. understandably. I couldn't get through 4 songs.

Sufjan Stevens - Carrie and Lowell is probably a contender for saddest album.

otm, I could listen to that one twice all the way through, and haven't revisited it since. songs are good, I just can't sink into that mood.

Little Green, Joni Mitchell – The wistful optimism is just heartbreaking

oh man, I was gonna mention that one. "A Case of You" as well, even if it's more bittersweet. "Little Green" is similar to "This Night Has Opened My Eyes" - the complicated emotions that come with having an abortion / giving up a child for adoption.

River too -- subject matter is kind of run-of-the-mill as far as sad songs but the treatment is especially heartbreaking.

joni mitchell - other people's parties

Inconsolable - Jonatha Brooke

Zabelle Panosian, Groung (The Crane)

https://www.youtube.com/watch?v=GizgyxGSrFs

The Train by Sinatra, off Watertown, a brutally sad album all told.

https://www.youtube.com/watch?v=dXP-417oiv0

Franz Schubert - 'Der Leiermann' (from Winterreise):

https://www.youtube.com/watch?v=sIIS-UgixGE

The Band - It Makes No Difference

the winner

Bruce Springsteen, “Brilliant Disguise”

Randy Newman - “Marie”

just thinking about that song, christ..