top 100 saddest songs of all time

Remember hearing this after some romantic disaster and it slayed me.

29. End of the Rainbow - Richard & Linda Thompson

28. Hospital - Modern Lovers

a hot summers day and sticky black tarmac
feeding ducks in the park and wishing you were far away

26. Crossroad Blues - Robert Johnson
25. Dark Was the Night, Cold Was the Ground - Blind Willie Johnson
24. River of Sorrow - Antony & the Johnsons

(My mother listened to far too many 70s complilations when I was a kid... which is why I know all these)

Not precisely sad, or funny, or disturbing, but some sort of middle ground - the chord arrangement and Jamie's delivery, though, make it strangely mournful.

12. "the bitterest pill" - the jam

11. "wise up" - aimee mann

I Hate Myself and Want to Die: The 52 Most Depressing Songs You've Ever Heard by Tom Reynolds
http://www.amazon.co.uk/exec/obidos/ASIN/1860746284/203-7908214-9069500

0. hardly getting over it - husker du.
-1. borrowed tune - neil young

Donny died during recording and Roberta's lyrics just go on and on without him... for about 10 minutes actually.... there is a lot of "I miss you" and futile language in this song.... it is really really sad in context.

I just put this up, if anyone's interested: The Walrus Magazine picks 30 of the saddest songs ever.

Includes contributions from sometime-ILX-person DaveM and, er, me. Feel free to leave some comments/abuse/recommendations.

Thanks, sorry, whorishness over.

mozart's requiem lol

Great list. FWIW, another good sad (rock) song is Grant Hart's You Don't Have To Tell Me Now, which is unsettling in how direct it is.

Some more that come to mind: Gregg Allman's All My Friends and his version of Jackson Browne's These Days, both of which are on the Laid Back disc; Chris Bell's You And Your Sister; The Clientele Dreams Of Leaving; Pernice Bros.' Number Two; Sun Kil Moon's Carry Me Ohio (not entirely sure about this one, but it feels right); Bruce Springsteen's One Step Up; Jimmy Cliff's Many Rivers To Cross; Richard Hawley's The Ocean (Again, I'm not totally sure about this one. In some ways, Hawley sounds hopeful and content; in others, he sounds like he's lost so much time and he's saying goodbye); and 2/3 of Billie Holiday's catalogue (and a good deal of Iron & Wine's early catalogue).

Gnossienne No. 5, Modéré

Biz Markie - Alone Again (Naturally)
[Grand Upright Music, Ltd. v. Warner Bros. Records, Inc.]

Hello In There--John Prine

Did I see "Thousand Dollar Wedding" upthread? Not sure.

KATY SONG - RED HOUSE PAINTERS - shush

Can't believe this wasn't metioned: "I Know it's Over" - Smiths

"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