I just saw this article and thought it was appropriate to this thread:
 

Cry Me A River: The 20 Most Heartbreaking Songs Of All Time! I don't have time to read it properly yet so I'll get back to it later. Any of you well up to the songs listed?

It may be a distance thing, but I didn't know more than half of them.

BTW, Soft Cell did something apart from "Tainted Love", a personal fave?

Otis Redding and Bonnie Rait are both in my cry/sing repetoire.

Dock of the Bay, Lil?

this one got me last night...
 

Trace Adkins was doing a tour of 11 shows in 10 days for the USO

Arlington by: Trace Adkins

I never thought that this is where I'd settle down,
I thought I'd die an old man back in my hometown,
They gave me this plot of land, me and some other men, for a job well done,
There's a big white house sits on a hill just up the road,
The man inside he cried the day they brought me home,
They folded up a flag and told my mom and dad, we're proud of your son

[Chorus:]
And I'm proud to be on this peaceful piece of property,
I'm on sacred ground and I'm in the best of company,
I'm thankful for those thankful for the things I've done,
I can rest in peace, I'm one of the chosen ones, I made it to Arlington

I remember daddy brought me here when I was eight,
We searched all day to find out where my granddad lay,
And when we finally found that cross,
He said, "son this is what it cost to keep us free" Now here I am,
A thousand stones away from him,
He recognized me on the first day I came in,
And it gave me a chill when he clicked his heels, and saluted me.

[Chorus:]
And I'm proud to be on this peaceful piece of property,
I'm on sacred ground and I'm in the best of company,
I'm thankful for those thankful for the things I've done,
I can rest in peace, I'm one of the chosen ones, I made it to Arlington
And everytime I hear twenty-one guns,
I know they brought another hero home to us

We're thankful for those thankful for the things we've done,
We can rest in peace, 'cause we are the chosen ones,
We made it to arlington, yea dust to dust,
Don't cry for us, we made it to arlington

I love that song. I'll have to find it on cd.

More like a "deep cut" thing, I reckon. I know (or know of) nearly every act on the list, but the bottom half (with the exception of Smoky) seems to be all cuts from albums that never got any airplay to speak of. I'd have to agree with lil, Otis & Bonnie have the most heart-rending sad songs on the list that I know.

Soft Cell, only other track I recall was "Tainted Love" morphed into a synth-pop version of "Where did Our Love Go".

First Cut is the Deepest- I love that one.

I finally had a second to click the link posted earlier. I recognize only a few names and none of the song titles. Now I feel really young and inexperienced. Ironically, I find that feeling somewhat depressing. Oh well, another good song if you listen to the lyrics is the Edmond Fitzgerald by Gordon Lightfoot.

"Wreck of the Edmund Fitzgerald" is a wonderfully sad & somber song. When it first came out, back in the 70s, I had no idea that it was about a contemporary shipwreck that had just occurred in the Great Lakes a few months earlier. Gordon Lightfoot created that instant classic that sounded so much like an old sea shanty, I thought it must be about some ancient historical incident.

Another poppy-trippy song was "Why do you build me up, Buttercup".

So sad and we didn't know it, lost in the music.

I'll 2nd "First Cut is The Deepest" and "Wreck of the Edmund Fitzgerald". Duran Duran's "Ordinary World", "Your Song" Elton John, "Weekend in New England" Barry Manilow, "Nowhere Man" Beatles & "Rainy Day People" Gordon Lightfoot..."Another Day in Paradise" Phil Collins.

I added a link to "The First Cut is the Deepest."
Just a few years ago, after hearing the cover done by Cheryl Crow, I felt it was empty, and lacking depth. I had heard my guy Cat Stevens on the records I owned many, many years ago (a coupla decades) and am refilled with the emotion originally felt in the lament.

From the list I posted the link to, I think the only one I've actually shed tears to is Sinead O'Connor's Nothing Compares 2 U. What a great song.

Another Sinead O'Connor song guaranteed to make the tears fall down my face is My Special Child :boohoo:

This song, Act Naturally, had me sobbing at work yesterday

This Aussie tv show theme tune used to make me cry :o

...and this one :o :o :o

In the midst of my ongoing project of ripping my entire CD collection to my 'puter (just got an MP3 player w/extra memory), I found my Four Tops greatest hits, & while I could pick almost anything Levi Stubbs ever sang as a great one, this one has the power of a great tear-jerker coupled with the Voice that I'm certain is leading the heavenly choir now...

P.S. ; It's been brought to my attention that the above link may not be available to non-US users...it is a link to YouTube, Four Tops, "Ask The Lonely"