One of the saddest songs I know is "Rider on an Orphan Train" written by David Massengill. Best version is done by Tom Russell.

Here’s a very sad one that I am listening to as I type this: The Circle is Small by Gordon Lightfoot.

The saddest song of all, written and performed by the immortal Hank Williams:

"Cold, Cold Heart"

I tried so hard my dear to show that you’re my every dream.
Yet you’re afraid each thing I do is just some evil scheme
A memory from your lonesome past keeps us so far apart
Why can’t I free your doubtful mind and melt your cold cold heart

Another love before my time made your heart sad and blue
And so my heart is paying now for things I didnt do
In anger unkind words are said that make the teardrops start
Why can’t I free your doubtful mind,and melt your cold cold heart

You’ll never know how much it hurts to see you sat and cry
You know you need and want my love yet youre afraid to try
Why do you run and hide from lies,to try it just aint smart
Why can’t I free your doubtful mind and melt your cold cold heart

There was a time when I believed that you belonged to me
But now I know your heart is shackled to a memory
The more I learn to care for you,the more we drift apart
Why can’t I free your doubtful mind and melt your cold cold heart

Here, it’s Don McLean’s ‘American Pie’. (In memory of Buddy Holly). One of my all time favorites. And taking years, more like decades trying to decipher what the heck he was saying has finally come out. You can Google it for the answer.. But it used to be a great drinking tune, until your mind came back to life and started thinking about it.. Here’s another link that may be of interest: http://www.don-mclean.com/americanpie.asp

Love Hurts – Nazareth

The queen of sad songs right now is Lucinda Williams. Awesome songwriter.

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Originally posted by BuddyRoadhouse

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Originally posted by enginecapt

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Originally posted by improviser

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Originally posted by enginecaptThe Band Played Waltzing Matilda by The Clancy Brothers

I second that, enginecapt. One of my favorite songs.

Here’s a version of that by The Pogues:

This was the first song that jumped into my mind when I read the topic line. It was actually written by an Australian (I think) folksinger named Eric Bogle. The Pogues did this cover version of it, produced by Elvis Costello. Great stuff. Shane MacGowan’s half (or more) drunken voice captures the sorrow of this song beautifully. Makes me cry every time I hear it.

There are some outstanding nominees listed here, but "The Band Played Waltzing Matilda" will take on all comers.

Buddy

Listen to the same song done by June Tabor and tell me which you thinkis most heart rendering.

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Originally posted by BuddyRoadhouse

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Originally posted by enginecapt

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Originally posted by improviser

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Originally posted by enginecaptThe Band Played Waltzing Matilda by The Clancy Brothers

I second that, enginecapt. One of my favorite songs.

Here’s a version of that by The Pogues:

This was the first song that jumped into my mind when I read the topic line. It was actually written by an Australian (I think) folksinger named Eric Bogle. The Pogues did this cover version of it, produced by Elvis Costello. Great stuff. Shane MacGowan’s half (or more) drunken voice captures the sorrow of this song beautifully. Makes me cry every time I hear it.

There are some outstanding nominees listed here, but "The Band Played Waltzing Matilda" will take on all comers.

Buddy

The Scientist by Coldplay, and almost anything by Rachael Yamagata make me get the blues (or sympathize with them). A lot of people talk about music and play lists at http://www.pandoradiscussionarea.com too if you’re interested in talking about music more….

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Originally posted by Tony Bad

Hurt – The originalTrent Reznor/Nine Inch Nails version is eerie and is what I feel and almost unequaled musical glimpse into someone’s soul, but Johnny Cash’s version is stunning, and especially remarkable considering it is a cover. The video is also amazing. I recall reading how Trent Reznor said the song wasn’t his anymore after seeing Cash’s video.

…some others…

My Way – Sid Vicious

I Hung My Head – original by Sting is sad, but again, Johnny Cash’s version makes me want to cry.

Atlantic City – Bruce Springsteen, who has a lot of sad songs…like Stolen Car, My Father’s House, the River, Brilliant Disguise

Bad – U2 this is a remarkable version from Live Aid

You Can’t Put your Arms Around a Memory – Johnny Thunders

Tony Bad,

Since you made this post, I can’t stop listening to "You Can’t Put Your Arms Around A Memory. I consider myself fairly knowledgable about music, and I’ve never heard this song before. I’ve since downloaded it for my mp3 player, and can’t stop listening to it. I just wanted to thank you for mentioning it. What a great song.

"People Who Died" by the punk poet-singer Jim Carroll packs a wallop 27 years after I first heard it.

Today I was unfortunately reminded of this sad song,Keep Me in Your Heart by Warren Zevon…recorded shortly before he passed away. Zevon was on Letterman quite a lot, and made his last big public appearance there. This clip has some of that appearance…including his advice on life and death, which was to"Enjoy Every Sandwich". Words to live by!

I hope I’m right on titles,Roy Orbison’s "Cryin." "But you don’t know me… lot of artists have done this, I think Ray Charles’ version is the best.

Then the worst Christmas song ever, "Bells will be ringing… or is that "Please Come Home for Christmas?, I think Charles Brown sang it first, and his version is probably the saddest.

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Originally posted by tmiles

Some of you folks could write a book. Take away the common interest in food, and this is still a very special group[8D]

Very, very well said, Tmiles. I was thinking the same thoughts. This is a very interesting thread, and as a music fan I’ve learned a lot of new music by monitoring this thread.

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Originally posted by JakerDog
There was a song in Toy Story 2 that ripped my daughters heart out. I don’t know the name but it’s sung by a toy doll that misses the days when she was a most loved doll and know has spent years under the bed.

And most Christmas songs, especially "I’ll be Home for Christmas"

When She Loved Me by Sarah MacLachlan and yes for I’ll Be Home For Christmas…