Most achingly beautiful songs ever

"The Moon is a Harsh Mistress" sung by Radka Toneff

If you like the Skye Boat Song, you might like the Mingulay Boat Song too, Sampiro.

How 'bout:

“Black Boys on Mopeds” - Sinéad O’Connor

And from the world of show tunes:

“Pretty Women” (from Sweeney Todd)
“Not While I’m Around” (from Sweeney Todd, with added bonus of copious Patti Lupone cleavage)
“Fifty Percent” (from Ballroom)

For the hippies: Mountain’s “For Yasgur’s Farm” http://www.youtube.com/watch?v=OQfR6LHvxag

Nat King Cole’s “O Holy Night” http://www.youtube.com/watch?v=_4dUxSq8gpk

Pachelbel’s Canon in D Minor http://www.youtube.com/watch?v=hOA-2hl1Vbc

I’ll be back with more later.
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Anything by Lorena McKennitt.
Bridge Over Troubled Water - Simon and Garfunkle.
Riders On The Storm - the Doors (maybe more hypnotic than beautiful, though)
At Last - Etta James

Art Garfunkel-Bright Eyes

Yikes!
I forgot Roxy Music’s “Avalon” http://www.youtube.com/watch?v=sA8ki5EG584&feature=related

The first song that popped into my mind was also Jeff Buckley’s Hallelujah, but I will also contribute “I Will Follow You Into the Dark” by Death Cab for Cutie.

Yeah, this, by a long shot. I’m not sure I’ve ever heard anything even close.

ETA : I also love the original version of Jersey Girl, by Tom Waits.

Joe

I have to agree with your assessment of Alan Parsons, but I’d have chosen The Traveller (Days Are Numbers).

The Freshman by The Verve Pipe

I’d replace that with their version of Theme From An Imaginary Western.

And that with his Wooden Planes.

This is my and my wife’s wedding song.

I can’t link to YouTube from work, but:
Samba Pa Ti, by Santana

I Still Haven’t Found What I’m Looking For, by U2, but the version from Rattle & Hum when they perform it with the Harlem Church Choir. Turn it up to 11.

Reading through the thread I’ve found bunches I agree with but my kneejerk, unvarnished pick just from reading the title was David Ford’s Go To Hell, in particular the linked version with the strings. That’s what adds the ache for me.

Alison Krauss’s cover of Keith Whitley’s When You Say Nothing at All. It’s a sweet song on its own, but her voice puts it way over the top into really beautiful. I like the various live versions best; the studio cut is a little heavy on some of the instrumentation. I love how Krauss’s voice often seems like it’s just on the verge of descending to a whisper. It gives the song a real intimacy; like she really is singing this right to me.

She’s also on my “Achingly Sad” list with Whiskey Lullaby (with Brad Paisley). My God, that song makes me cry like a little baby. “He put that bottle to his head and pulled the trigger” has got to be one of the saddest lyrics in popular music.

Of course, I’d be tempted to put Alison Krauss’s cover of the Des Moines, Iowa phone book on this list. She’s just got that kind of voice.

Dido’s Lament from Henry Purcell’s opera- “Dido and Aeneas”

When I am laid in earth

I like most of what has been posted, but Beethoven Violin Romance No.2 is the only one that brings tears to my eyes.

Excellent call.

Most romantic pop song of all time (a slightly different category)…Hollies, The Air that I Breathe.

And I’ll add Sarah Brightman / Andrea Bocelli, “Con Te Partiro”. Preferably while watching the fountains at the Bellagio, Las Vegas…one’s heart practically explodes with pure joy.

My last post had all songs by female singers. I thought I’d balance it out with some men:

Today - Jefferson Airplane

Follow - Richie Havens

Imagine - John Lennon

Pink Moon - Nick Drake

Sadly Beautiful - Paul Westerberg

Agree highly with both of these, and think you’ll also appreciate Mad World, as performed by by Gary Jules.

Some others that (I think) haven’t been mentioned:
Everyone loves “Hallelujah,” but Lover, You Should’ve Come Over by Jeff Buckley is wonderful.
No Lies, Just Love – Bright Eyes. This song actually makes me cry.
Naked As We Came – Iron and Wine
Come And Find Me – Josh Ritter
Damien Rice – Cannonball