Dar Williams has some of the saddest, yet beautiful songs. Of these, I pick “End of the Summer” as the most likely to make you “cry, cry, cry”.
I’ll also vote for Taps:
Beethoven’s Sonata, Pathetique, which, among others, was played on many radio stations for 3 days folllowing President Kennedy’s assassination:
Mahler’s Symphony No 5, the theme from Death In Venice:
And for bucket kicks, Dr. Elmo’s Grandma Got Run Over by a Reindeer:
I’ll add Edith Piaf’s version of Autumn Leaves:
And any version of September Song, but especially Walter Huston’s, Jimmy Durante’s & Frank Sinatra’s:
No one seems to has mentioned these two yet, which surprises me
Wicked Game - Chris Isaak
Seasons in the Sun - Terry Jacks
Also I’ll give a mention to Circle, Edie Brickell & the New Bohemians.
Oh my goodness, did you do it? Is there audio or video? My brain is bending into pretzel shapes just thinking of that song on those instruments. I want to hear!
You’re right, I’m wrong. It’s “made to rest.” To think that all these years I was hearing the wrong lyric! Of course, knowing her, that could still mean the kid was murdered. I’ll ask her.
Sorry for the hijack folks.
Really, a sad music thread in which nobody has linked Tom Smith’s A Boy and His Frog?
I’ll be the first to admit it cheats by playing on childhood memories, but it really should get bonus points in that the writer and performer couldn’t get through it without choking up.
Dire Straits, Brothers In Arms. I guess it’s supposed to be uplifting but I can hardly bear to listen to the whole thing.
“In the Winter” by Janis Ian
I get irrationally angry about Terry Jacks’s version. Rod McKuen fucked up a genuinely moving - but subtly ironic - song by Jacques Brel called Le Moribund where a dying man talks to each of his nearest in turn, revealing his ill treatment at their hands.
Which reminds me, Ne me quitte pas (“Don’t leave me”) is another one of Brel’s that McKuen destroyed with “If you go away”. And it’s another song that I can’t get through - purely because of the devastating raw emotion of his original live performances (subtitles provided).
These are just plain sad as hell:
“In the Quiet Morning” by Mimi Fariña and Joan Baez is the saddest thing I’ve ever heard.
“Digging for Your Dream” by Indigo Girls.
Also by Indigo Girls, the 3rd stanza of “Ozilline” if you’re a dog lover. 
These make me cry:
“The Journey On” by Kate Price makes me bawl like a baby every single time. Many years have passed and my time now grows short. The journey becomes harder every year. I know the day will come when I will be the one who’s left behind by those who I hold dear. And life will lead before them and life will carry on. When my days are done they will carry on. When the western gate has opened she will call me to her breast and it’s in my mother’s arms I will rest. There’s nobody else like Kate Price. She’s going to be my entry in one of those “greatest artist no one’s ever heard of” threads.
“Silent Legacy” by Melissa Etheridge is another guaranteed three-hanky song, though that one is directly connected to my own personal history, which the OP ruled out.
“Southland in the Springtime” by Indigo Girls makes me cry from the sheer beauty of it, especially when I’m driving in my home state of Virginia alongside the Blue Ridge wondering… the South is so beautiful why does it have to hate queers so much… very mixed emotions…
“Dante’s Prayer” by Loreena McKennitt is another of those that make me cry from the sheer beauty of it.
I’m going to have the Flower Duet from Lakmé played at my funeral. That is going to be so cool. Wish I could be there.
hapaXL, Ulali’s singing makes electric chills all up and down my spine.
An Arky, “Long Black Veil” is so very old-fashioned romantic as well as Southern Gothic. They just don’t make 'em like that any more.
Imago and Equipoise, thanks for turning me on to Happy Rhodes & “Warpaint.” Wow. That really works for me. Instead of sad it makes me feel inspired & empowered in a grimly-determined sense. I’m really getting a lot out of that song. It reminds me of what making songs is all about.
We did, but there’s no audio and if there’s video out there I don’t know about it. However, we do still play once in a blue moon, so I could talk to her about doing a recording or even just performing it again now that people are more likely to whip out cellphone cameras.
Best to private message from here on to reduce hijacking damage, maybe?
You’re welcome 
.
The song I had mentioned as being sad is not “Warpaint” but the much more lachrymose “Ra Is a Busy God”. I definitely agree with you that “Warpaint” has a strong grimly triumphant type vibe.
I’ll put this hijack for Johanna & Imago in spoilers so people can skip over it easily.[spoiler]
Johanna, melt I’m so glad you love the song “Warpaint.” It’s one of my favorites. It means a lot to me too. Thank you for saying so.
I would dearly love to see it. Happy answered me regarding the meaning of Ra Is A Busy God. I sent her what you wrote.
[QUOTE=Happy Rhodes]
RE: Ra Is A Busy God
Hi V,
Yeah, whoever this is, they actually nailed the overall feeling I was going
for. Although the lyrics were not as metaphorical as all that. As you know,
I wrote the music first for the Ambient CD that Aural G put out. But it was
my favorite piece of music and I really wanted to use it further. To this
day, it’s still one of my favorite tunes,(of mine obviously.)
Now, if an analyst were to examine these lyrics, they’d probably conclude
exactly what this person did. That I’ve had abandonment issues. Yes.
However, when I wrote this, I wasn’t consciously thinking about that. I was
actually thinking very literally about the sun and how sad it made me when
it descended over the hill. I watched many sunsets while writing those
lyrics. The idea is HOPE. The sun always represents hope for people. “The
Sun’ll come out…tomorrow…” “Here comes the sun…doooten doo doo”
“Sunshine on my shoulder makes me happy…” “I’m walkin’ on sunshine…”
You get the point.
You know how when you fly on an airline…sometimes it’s overcast or
raining where you take off. But once you get to 30,000 feet, you’re looking
at bright sunlight. The sun is always shining on SOMEONE, somewhere. He’s a
God who has to take care of every hopeful person on this planet. So I guess
you could say that I wrote this song from the perspective of a child who has
7 billion siblings and has parent-envy.
Later,
H
[/quote]
If you want to join the Happy Rhodes Group on Facebook to discuss her more, let me know and I’ll send you the link. There’s a Page and a Group. Group is better.
[/spoiler]
I was thinking about my previous picks and I want to add:
Seasons of the Heart-John Denver
Makes me cry every time I hear it.
Haven’t read the entire thread so I don’t know if it’s already been mentioned, but I’m embarrassed to admit that I consider Bobby Goldsboro’s Honey to be the all-time tearjerker extraordinaire.
Any and every song from my youth is the saddest song in the world. Damn, the years have flown, so many hopes and dreams unrealized.
Yes, on September 3rd, 2002.
I think I found it and sent a request to join the group… pm me…
[spoiler]I’d definitely like to join the group!
And that addition to what I’d already thought of on the song is amazing. It floors me how both fit and then when you match them up it’s something different from either- would it be fair to say that in a single line the lyrics translate to “hope abandons me from time to time, but I don’t abandon hope” on its most moderate level, with the parts about the sun as the direct presence of hope being more conscious than this and the parts about unreturned devotion being more unconscious than it? Awesome how she gave you such a detailed and honest reply- that takes guts for any artist.[/spoiler]
I’ll second that, “Time” always makes me sad.
TLC (or is it Salt and Pepa?) “Waterfalls”.
And I’ll cast the 5th (10th? 20th?) vote for Danny Boy.