Don Henley’s ‘A Month Of Sundays’ (performed at Farm Aid 1985) about an old farmer looking back on his life, bemoaning how hard life is nowadays for ‘the independent man’. Very sad and very beautiful.
beagledave mentioning Springsteen reminded me of, for me, his most beautiful sad song: Racing In The Street.
I am not keen of sad country songs, I’ve been over-cliched with them.You have to have a heart as hard as stone not to laugh out loud at most of them. So I suppose I’d better put up.
Moira Kerr Mclain of Glencoe
I’m surprised that Angel by Sarah Mclachlan has not had a mention
Sandy Denny - Who knows where the time goes
Everthing but the girl - Missing - Acoustic version (very haunting song)
Massive Attack - Protection
Bread - Diary
Mary Chapin Carpenter - Only a dream
The Walker brothers - No regrets - cheesy vid but good sound quality
If you have ever been to the place where this song is, this will hit home
Eleanor McEvoy - The heart of a woman
Don Maclean - Castles in the air
Don Maclean - Empty Chairs
Gordon Lightfoot - The way I feel
George Michael - You have been loved
Beth Orton - She Cries your name
I refuse to listen to John Prine’s “Hello in There” anymore. An avalanche of youthful guilt and the fear of growing old.
Neil Young’s “Needle and the Damage Done” gets me, as do many other songs about wasted potential. Pink Floyd’s “Shine on you Crazy Diamond” is another.
The Wreck of the Edmund Fitzgerald
I used to live in Ohio, and when they’d get to the line “just 20 miles from Cleveland” it would give me shivers.
Apparently I have a really bad memory…here are the actual lyrics that I conflated:
“When they left fully loaded for Cleveland
…
The searchers all say they’d have made Whitefish Bay
If they’d put fifteen more miles behind her.”
Is it Over Yet? By Wynonna.
Although it’s specifically about a relationship songs this poignant remind me of the sense of loss that comes with drastic change and loss that can come in many forms.
Don Maclean’s “Vincent” gets me every time.
Kristofferson’s “Jody and the Kid”
“Glenn Tipton” by Sun Kil Moon is another one that has made me weep on occasion.
Also
On Raglan Road- Luke Kelly
There Were Roses - Cara Dillion
“Without Your Love” - Roger McGuinn, from the Back From Rio CD
The deep quaver in McGuinn’s voice just guts me. Add David Crosby and Chris Hillman doing sad, sad harmonies, and it’s a real tearjerker. I can’t even sing the song, because I get choked up about halfway in. Something about that plaintive tone just does me in.
I’ve always characterized this song as"music to write your suicide note by".
The Green Fields Of Canada - Mary Dillon.
I feel like this song could go either way though. If you watch it in the Ken Burns Civil War doc then yeah it’s sad but if you listen to it on it’s own, it’s not so sad. Maybe I’m just saying this in order to justify me using it for my wedding coming up. I will be walking down the aisle to this song.
Anywho…These are my puddle inducing songs…
I came on here to vote for Into the West by Annie Lennox that plays during the credits for Return of the King.
“Hope fades into the world of night. Through shadows falling out of memories and time. Don’t say we have come to journey’s end. White shores are calling, you and I will meet again.” Ugh.
Another vote for When Somebody Loved Me and If You’re Reading This. The first time I heard the latter I was in the car and had to pull over because I couldn’t see the road through my tears.
Stay With Me from Into the Woods.
"Don’t you know what’s out there in the world?
Someone has to shield you from the world.
Stay with me.
Princes wait there in the world, it’s true.
Princes, yes, but wolves and humans, too.
Stay at home.
I am home.
Who out there could love you more than I?
What out there that I cannot supply?
Stay with me.
Stay with me,
The world is dark and wild.
Stay a child while you can be a child.
With me."
Both already mentioned, “Cat’s Cradle” is the first thing that comes to my mind. “Tears In Heaven” too, when I remember the real life circumstances of Clapton writing the song.
I remember this song becoming a surprise hit after it was featured on that episode of the 1980s sitcom “Family Ties”. Very good.
“Operator” by Jim Croce does it for me (much more so than “Time In A Bottle” which isn’t particularly sad to me, just treacly in a way that I like), as does “Old Friends/Bookends” by Simon and Garfunkel.
A Cole Porter song “So In Love”, already rather haunting in its intensity, was given a tragic twist that will always remain in my mind when k.d. lang sang it with a video for “Red, Hot + Blue”, a fundraiser for AIDS research in the early 1990s. The video depicted someone going through the motions of putting away the belongings of a lover who’d just passed away. Turning that song of desperate love into one of mourning is devastating.
I haven’t heard it in that context but thinking of Roberta Flack’s version of “The First Time Ever I Saw Your Face” as a farewell would also be gut-wrenching.
Agreed. This is what I meant, but failed to say.
Nah, you’re right. That will be a beautiful wedding piece.
Unsolicited advice: Wear rubber-soled shoes in case the aisles are wet-- your guests will already be feeling emotional, and that song will open the floodgates.
Have a good one, and congratulations.
Holding Back the Years, Simply Red
Yes, that’s the one I thought of too. His voice is heartbreaking.
Richard Shindell’s Wisteria. There are no good YouTube clips of his songs (they are all crappy cell phone recordings). At least the audio on this version is not too bad.
Hands down, for me it’s *He’s My Son *by Mark Schultz. I can’t link it right now, but I wouldn’t if I could because just a tidbit would do me in.
It’s a prayer by a father of a very ll boy, and you can feel his desperation, fear, confusion, and pain.
Softly and tenderly jesus is calling…calling for you and for me…
If “saddest” can be bent to mean “most depressing”, then I’d say James Baker singing “Ain’t No More Cane.”