Most achingly beautiful songs ever

Just to add to the flood of replies I’ll submit The Art Of Suicide by Emilie Autumn.

It’s my New Favorite Thing.

Some cracking ones already mentioned.

One that hasn’t “scattered Black and whites” by elbow

I think the man has infiltrated my childhood!

Casimir Pulaski Day - Sufjan Stevens
Mellon Collie and the Infinite Sadness - Smashing Pumpkins
Lullaby - The Dixie Chicks
Save Me - Aimee Mann

If I’d kept going with my listings (which was tempting!) I’d have certainly included that one. And “Shadow of a Lonely Man”. And “May Be a Price to Pay”. And “Dr. Tarr & Professor Fether”. And “The Eagle Will Rise Again”. And…

Anyone yet mentioned Fairytale of New York by the Pogues?

If somebody already mentioned these two versions, I missed seeing them.

I’m one of those people who believe a “song” has to be sung. However, I’ve adjusted my thinking for the sake of the majority opinion at SDMB and include
Blue in Green by Miles Davis and
Tommy Emmanuel - Somewhere Over the Rainbow
as two of the ones that do it for me every time I hear them.

Icarus.

The original (Paul Winter Consort, with David darling on cello)

Ralph Towner (the composer and guitarist)

LAGQ-The LA Guitar Quartet goes all fancy-schmansy on it…

I prefer the original.

Actually, there are three pieces to Op. 9. And while I love No. 2 - my wife plays it, and it’s also her favorite piece - I absolutely love the lesser-known but hauntingly melancholic No. 1. It’s deceptively hard; my wife still struggles with it.

And I forgot to add: Music of the Night, from Phantom of the Opera

I’ve heard that Sting said that her version is his favorite but I don’t have any primary evidence

Glad to see the Smashing Pumpkins getting some love by the OP, though I’d suggest the most achingly beautiful song in their catalog is Luna.

But my top most achingly beautiful song is Sigur Rós’ Glósóli. Their aforementioned Untitled 4 is a close 2nd.

A few more, just for the halibut:

“Cool Change”, Little River Band

“Seven Bridges Road”, The Eagles

“Rose of Cimmaron” and “Crazy Love”, both by Poco

“Calypso”, Suzanne Vega

and of course,

“Dust In The Wind”, Kansas

Interesting side topic: What makes a song “hauntingly beautiful”? From my own selections, I clearly prefer strong vocals and vocal harmonies, but that’s just me. What do the rest of you find “haunting”?

In My Life - The Beatles
Whiter Shade of Pale - Procol Harum

Apologies if I 've missed it, but I don’t think I have.

Puccini’s “Un bel di vedremo”, from Madama Butterfly.

Arvo Pärt - Cantus in Memory of Benjamin Britten

Just these heart-breaking washes of strings with a church bell punctuating the sound. Off of the album Tabula Rasa, which in its entirety is achingly beautiful.

Max Richter - On the Nature of Daylight from his 2004 album, The Blue Notebooks, which is amazing.

I’ll see your “Homeward Bound” and raise you one “The Boxer”!

I want to understand why things like this happen. I wonder if there are some themes that go through a lot of these songs–some kind of chord progression, some key they may be in…I wish I understood music theory better.

Not sure, but I came in here to mention The Pogues’ “Lullaby of London”:

Not really “songs”, per se, but I consider Mozart’s work to be our civilization’s standard for beautiful music. K364 (Sinfonia Concertante in E-flat major (I think)), the piano concertos, Symphony 41, 4th movement.

Seems to me we have a confusion of terms, and not just a difference of opinions.
Achingly beautiful in what way? Lyrics? Instrument/sound? Ambiance? Combination?

Some songs are lyrically beautiful. Some have beautiful musical arrangements. Others show an amazing pure beautiful vocal ability. A rare few have all.

All of these are a matter of opinion, of course. Ear of the beholder and all.

Just had to get that out there, because I read some people’s entries and think “WTF! Really?”

Good call on “Vincent”, Sam Stone. I came in to say that.

Since you took it, I’ll add Elton John’s “Tiny Dancer” and “Levon.”