Your most painfully beautiful song

I’m almost embarrassed to start this thread, but what I mean are those songs that would bring a tear to your eye if you were in that sort of sentimental mood.

One for me is Autumn Leaves, Eva Cassidy’s rendition in particular.

엄마야 누나야 (Mom and sister) is another one. It’s based on a Korean poem about a young boy naively suggesting to his mother and sister they live by the river. I can’t quite figure out if I feel this way about the song because it was a favorite song of mine when I was little kid (which I’ve recently rediscovered) or something else entirely.

Oh I’m missing you by Christy Moore - the song of a derelict Irish alcoholic, stuck in London because of the shame of returning home as a failure. Gets me every time.

Guldet blev till sand, a Swedish song from the musical Kristina från Duvemåla. It concerns a Swedish immigrant to America who goes west in search for gold and persuades a friend - a rather simple-minded fellow - to come with him. They starve and thirst and the friend begs him to go back, but he refuses. His friend drinks water from a stagnant, stinking pond and dies. Eventually he returns, bringing only his friend’s pocket watch.

“Lover, You Should’ve Come Over” by Jeff Buckley

“The River” by Garth Brooks.

Easy:

Three Babies by Sinead O’Connor

I can put the headphones on, crank it up and cry for hours any time I like. But it’s my dead baby she is singing about.

Jeff Buckley’s “Hallelujah.”

“Bonny”- Prefab Sprout

Footsteps by Pearl Jam: video | lyrics

Talk of the Town by the Pretenders…wistful, about unrequited love, and makes me wish I could sing like Chrissie Hynde

lyrics

Homeward Bound…the Mormon Tabernacle Choir version is beautiful, but I prefer the Navy Band Sea Chanter’s version personally.

Lovedrug “Happy Apple Poison” download it 1/3 down the page here

I can’t quite explain why, but there’s something about the melody and the tone of the backing vocals, not the lyrics, that feels like heartbreak every time I listen to it.

This song doesn’t make me cry but it does hit me for some reason.

The Queen and the Soldier by Suzanne Vega

Two for me:

Angel - Sarah McLachlan, played at our grandson’s funeral

Little Drummer Boy - After the homeless vet episode of West Wing, this song is painfully beautiful

Okay, so I assume we’re to go for the most humiliating song that moves us to tears.

For me, this would be the song ‘‘Now That I’m a Woman’’ from The Last Unicorn. Yes, this song is in fact about a unicorn’s reaction to being transformed into a woman. At least, that’s what it’s about when you see it as a little girl. The entire movie is a sort of epic metaphor for the risk and regret inherent in adulthood, along the same lines of Alice’s Adventures in Wonderland. So I watch it, I remember a time when I didn’t realize what it was about, and I cry.

Once, I can’t remember
I was long ago someone strange
I was innocent and wise and full of pain
Now that I’m a woman
Everything has changed…

There you go.

slinks away in shame

I second Little Drummer Boy. That song tears my shit up… and I’ve never seen West Wing.

I do love this version, too.

However, I must offer a different one for this category: Tabula Rasa by Arvo Part (Amazon link). It is a modern classical piece for strings (cello’s mostly) that was featured in a New Yorker piece. They described how terminally patients tend to gravitate towards it because it has the complexity of sadness mingled with the optimism of arrival - they call it the music of the angels.

It immediately came to mind as perfectly fitting the OP.

“A Summer Song,” by Chad & Jeremy. The song for everyone who’s ever had a summer love.

‘Jezebel’ by Iron + Wine

It’s a bad quality fan video (though the music sounds ok) so it takes a second for them to start the song, but it’s worth a listen if you haven’t heard it.

Tossup between Sting’s Fragile, Peter Gabriel’s Biko, Gabriel & Kate Bush’s Don’t Give Up, Shelleyan Orphan’s Century Flower, or This Mortal Coil’s Mr Somewhere or The Jeweller. Right now, it’s Shelleyan Orphan, but tomorrow - who knows.

Waltz #2, by Elliot Smith