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Nora Jones Somewhere Over the Rainbow

Heavy Horses by Jethro Tull is truly heart wrenching to me, in a lovely, melancholy happy way, about the vanishing of the role and way of life of the plougsman and the draft-horse. The tractor's on its way...

Busby Berkeley Dreams gets me every time.

"I should have forgotten you long ago
But you're in every song I know..."

Johann Sebastian Bach's Toccata & Fugue in D minor
Blue Dress by Depeche Mode
Johnny Cash's rendition of We'll meet again. It just gets tears in my eyes and a lump in my throat.

Oh, but it was only during the 1st movement of Tchaikovsky's Concerto for Violin and Orchestra Op. 35 (with Salvatore Accardo playing the solo violin) that I noticed I hadn't breathed since the clicmatic part started. It was that intense.

Oh, and of course I agree with

Wyrm wrote: The only one that comes to mind right now is the Cosmos theme music. It's that beautiful. Brings tears to my eyes every time.

This train don't stop- Elton John

There isn't any song that rips my heart out, nor can there be one since grief doesn't resonate well with music in me. However, I am drawn to songs with a certain melancholy or tragic element, which is somewhat in the same vein as the OP.

The Haunting, by Kamelot
A grief stricken man apologizes to the woman he seduced under the sorrowful delusion that she was his dead beloved.

Love You To Death, by Kamelot
Young love doomed by terminal illness.

Walk in the Rain, by Yoko Kanno
No clear story or message, but it's supremely melancholic. The music is like a funeral march and every lyric is streaked with anguish.