Oh dear gawd - I know it. For some reason, I think it was recorded by David Geddes, who also gave us the classic “Run Joey Run.” <Moved by reminiscence of this song, LifeOnWry takes a metal skewer and jams it through her ear and into her brainpan> I could be wrong about the “artist,” but I’ll find out.
I have been observed crying at a McDonald’s commercial, so I’ll just say here that there’s not too many songs that DON’T make me cry.
How’z about “And So It Goes” by Billy Joel?
Also a more obscure one: “The Coral Castle” by Andrew Peterson
Well as Eleanor Rigby and Leonard Cohen got props, it’ll make this easier for me. A lot of good ones mentioned, I’ll have to give a shoutout to How Soon is Now.
here are my picks however.
Radiohead - Street Song or Talk Show Host (I would say Knives out but that’s more cuz of personal experience)
Placebo - My Sweet Prince
Portishead - Sour Times
and as cheesy as it has become Candle in the Wind actually gets me.
and last but not least
Where the Wild Roses Grow by Nick Cave and Kylie Minogue. (the song that shocked a whole message board)
Erek
That’s a good one.
For me, it’s Mazzy Star - Fade Into You
Well, an English song that just spontaneously brought tears to my eyes the first time I heard it was
“Kisses sweeter than wine” (lyrics by Paul Campbell)
Another song/ghazal (in Urdu) that is terribly moving is
“Chupke Chupke” sung by Ghulam Ali.
I’m not sure it qualifies as a sad song, but this from The Cardigan’s LoveFool really gets to me:
“I don’t care if you really care,
as long as you don’t go.”
Sheri
hmm lets see…
Yuki Kaiura - Wake Wings
Martina Sorbara - Bonnie & Clyde II
Lynard Skynard - Freebird
Coldplay - Yellow
Sasha & John Digweed - Rabbit in the Moon - Out Of Body Experience
Fiona Apple - Across the Universe
Power Symphony - Never Dream of Goodness
thats all i can think of off the top of my head
Especially when it’s performed on an amplifier that goes up to 11.
Wow, jjimm, *John Doe No. 24 * is pretty powerful, especially if one knows New Orleans very well: St. Charles Ave., street cars, shot gun houses… It’s sad that no one said a word at the grave side (re: article).
For this category I always think of Madonna’s version of Love Don’t Live Here Any More. She puts a lot of passion into the song, IMHO. And it’s very sad.
Let’s see… Leonard Cohen’s been mentioned (although I think he’s really funny as well as sad),
“Holocaust” by Big Star
“My Father” by This Mortal Coil
“Northern Country” by Heidi Berry
“Sanvean” by Dead Can Dance
“In a Lonely Place” by New Order (“Ceremony” as well… but you have to know what happened for the real impact)
-fh
Have we had this thread before?
Hmmm… as far as Lynard Skynard goes I would have to say “Mr. Banker” or “Four walls of Raiford” are MUCH sadder. Lyle Lovett has some sad ones… “Baltimore” and “Family Reserve” come to mind. Gordon Lightfoot “The Wreck of the Edmund Fitzgerald” is pretty sad. Type “O” Negative’s “Red Water” is a sad christmas time song.
I’m not a huge Fiona Apple fan, but I have to admit I was entranced by her version of this song. Very soulful. The video is amazing as well.
A lot of modern singers have done versions of “Gloomy Sunday,” but none so well as Heather Nova. On her new album South, she has a deeply-moving rendition of it. Not as good as the original, though.
All this discussion has made me think of another song that has made me cry… sweet and sad.
“16 Days” by Lori Carson
There are lots of sad songs in my collection, but it’s possible to beat just about anything from 20th-c. pop by digging into the Renaissance composer John Dowland, whose oeuvre is full of ditties like “Flow My Tears” and “The Cypress Curtains of the Night” and “In Darkness Let Me Dwell” and “From Silent Night, True Register of Moans”. A little of this stuff goes a long, long way.
Another vote for Iris DeMent’s My Life, which my mother also hates with a passion as it happens. Sucks to her.
Johnny Hodges’ recording of “Blood Count” on Ellington’s And His Mother Called Him Bill was recorded shortly after Billy Strayhorn died, and is pretty devastating.
Bill Frisell’s “Strange Meeting” in the recording on Live. He’s recorded it many times but never to such desolating effect.
Gavin Bryars’ “After the Requiem”, which also coincidentally (or not) features Frisell.
There’s an aborted solo session by Bill Evans recorded shortly after the death of Scott La Faro in a car crash (only released in the 1980s on the Riverside boxed set); after cutting four tunes, including what must be the most downcast version of “Danny Boy” on record, he couldn’t go on & aborted the session. The producer Orrin Keepnews rightly remarked that it was a de facto memorial for La Faro.
Portishead “Roads”- Oh Christ, definitely in the running. How can something so gorgeous be so incredibly depressing?
I don’t care for Fiona Apple, either, but “Never is a Promise” is a tearjerker, especially if you know the story behind it.
For No One by the Beatles is one of the most relentlessly depressing songs I’ve ever heard.
Leeds by the Indigo Girls is powerfully sad. “Hold my head love, I’m sick tonight/Find the open hole and press your fingers there with all your might/Before the last ounce of my spirit bleeds/Onto the pristine sheets of the hotel bed in Leeds.”
And though it may be corny, I can’t even think about The Cat’s In the Cradle by Tom Croce without getting sad.
Heh, Ramasutra - Low always goes on my wrist slitting playlists, so I’ll have to add that one in there.
Nirvana - Heart Shaped Box as well.
The Dirty 3’s Everything’s Fucked always gets me going, as does any song ever by The Paradise Motel, particularly their Left Over Life To Kill EP.
When The Tigers Broke Free and most of the Final Cut album by Pink Floyd come under the “most depressing” tag for me.
However, the song that always gets me crying, every time, is The Color and the Kids by Cat Power, which isn’t so much sad as it is touching and nostalgic - a heartstring-tugging-tearjerker supreme.
Nothing makes me sadder than Drops of Jupiter by Train.
The line "And did you miss me while you were looking for yourself out there " gets me every time.
Of course, there’s “The Wreck of the Edmund Fitzgerald” by Gordan Lightfoot
[Richard Jenni]
"and the wave hit the boat and they died like rats…
[/Richard Jenni]
Shit, Drops of Jupiter just came on the radio.
Could someone please explain this reference?
For sheer weepiness, I prefer Jeff Buckley’s version of “Hallelejah” to Cohen’s. Buckley’s “Lover, You Should Have Come Over” is pretty damn sad too.
Ben Folds Five have a number of songs that manage to break me up. “Don’t Change Your Plans” and “Evaporated” in particular.
Hunters and Collectors “Throw Your Arms Around Me” does the trick too. Speaking of Hunters, Mark Seymour’s version of “Home Again” always threatens to make me cry if I’ve been travelling away from home for a while.
Smashing Pumpkins “For Martha” is about losing your mother, so that’s always pretty difficult to listen to. I still play it though when I’m feeling especially down. 
The Rolling Stones “You Can’t Always Get What You Want”.
In the painfully embarrassing category:
Mary Hopkins “Those Were the Days” and Don McLean “Vincent”. Oh, the shame.
Danny Boy