“Vincent” by Don McLean.
Billy Joel’s “Lullaby”
For me too. The “XO, Mom. It’s okay, it’s alright, nothing’s wrong” part just kills me.
…and Liberal, I’m so sorry.
Joan Armatrading’s The Weakness in Me. You can find Melissa Etheridge and Keisha White performing it on YouTube, but neither version holds a candle to Armatrading’s for emotion.
Romeo and Juliet by Dire Straits.
How very kind. Thank you.
Anachie Gordon as sung a capella by Sinéad O’Connor as an encore when I was at her concert in 1990. It’s beautiful no matter who sings it, but I’ve never heard it as heart-wrenching as her version that night.
I came in here to mention this song, but I see someone already beat me to it. So much emotion packed into this song…
Eva Cassidy covering Sting’s “Fields of Gold”.
Sinead O’Connor covering Elton’s “Sacrifice”.
Easy, without a doubt, “One Last Goodbye” by Anathema. It’s even more powerful when in the context of the song that follows it on the album, “Parisienne Moonlight”. Every single time it has come up on shuffle at work, someone invariably asks about it. I can only imagine that people who aren’t moved by it have simply never had their heart broken.
Who let the Dogs out?
The Kurt Weill song, “September Song.” The version I know and love is by Lou Reed.
Don’t be ashamed. The title song just kills me.
“Leader of the Pack.” Just… just the opening breaks my heart. Laugh if you will.
Wow, thanks for posting this. It’s one of my favorite songs and I had no idea she did a cover. It’s incredible.
And also the coolest! 
My responses-
This Woman’s Work- Kate Bush
By My Side from Godspell (the women know that Jesus is bummed but not quite why, and are promising total loyalty to him through whatever trials they face)
and a song I heard when it first came out 30 years ago, had no idea where it came from, and rediscovered this week due to a mention on another thread here- Forever Autumn from the Jeff Wayne Musical WAR OF THE WORLDS sung by Justin Hayward.
What a good suggestion! Tabula Rasa is probably the most aching and beautiful album I’ve ever heard.
As for my own contribution, I vote for “Some Grand Vision of Motives and Irony” by the criminally unknown Loud Family, off of their (great) album - “Plants and Birds and Rocks and Things”.
Nightswimming - R.E.M.
or maybe Goodbye by Steve Earle.
You’re welcome. 
Thank you for the link, haven’t seen that before.
There’s a ton of Sam Beam songs I would describe as painfully beautiful. In fact, I think “painful beauty” should probably be the name of the section where Iron & Wine is located in the record store.
I’d submit “Naked As We Came”, “Each Coming Night”, “Fever Dream” and “Passing Afternoon”, all from Our Endless Numbered Days, and “Faded From The Winter” and “Upward Over The Mountain” from The Creek Drank the Cradle.
(It’s almost impossible to find Sinéad’s version, but I’d recommend either Mary Black or Loreena McKennitt’s as the next best.)