I first heard Shirley Bassey’s recording of Ballad of the Sad Young Men back in the early '80s, when all my friends were dying of AIDS. That song will always remind me of those horrible years.
I think this is the original. Am I the only one who usually prefers, vastly, the original recording to new versions or “covers”? (Just after posting I searched and listened at Youtubes, and decided I’d better post a link to the “real” Thousand Kisses Deep! 
)
Some Lou Reed songs, especially “Heroin” and “Walk on the Wild Side”, also deserve mention.
‘The Drinking Song’ by Moxy Früvous. First heard it on the anniversary of the (way unexpected and sudden) death of one of my good friends. The line, “…Told him he couldn’t just die.” Gets me every single time. I sing along with it, and my voice always catches before the last word.
The Rolling Stones songs that “cut” me the most isn’t Angie (though that’s a very good candidate) but Memory Motel and Shine A Light.
You’re just a memory, of a love that used to be
And you used to mean so much to me
or
*Angels beating their wings all in time
With smiles on their faces, and a gleam right in their eyes
Thought I heard one of them sigh for you
Come on up now, come on up now, come on up now
Let the good Lord shine a light on you
Make every song your favorite tune
Let the good Lord shine a light on you
Warm, like the evening sun*
#1. Kesha’s “The Harold Song.” It’s even better watching her sing it live.
#2. Eric Carmen’s “Never Gonna Fall in Love Again”. I just recently found out (I think on SDMB) that the melody comes from Rachmaninoff’s Symphony No. 2.
#3. I pick the better-known Left Banke song, “Walk Away Renee.”
Torn by toad the wet sproket.
Never, EVER fails. Ever. It hurts me to hear it, but it’s beautiful.
Forgot Billie Holliday’s Strange Fruit, about lynching.
Into Dust by Mazzy Star - music to play while you search for a good strong crossbeam to toss a rope over…I have this burned to a CD, right before I Want To Party by The Venga Boys - they cancel each other out :D. (another sad one - The Reason by Hoobastank. There are a LOT of songs of this ilk, aren’t there?)
A couple of other Lou Reed songs - “Pale Blue Eyes” and “Street Hassle” …and I almost forgot “The Day John Kennedy Died”.
Good choice. But I’m going to go with Prine’s Bruised Orange (Chain of Sorrow). It is ostensibly a true tale Prine experienced as a youth about an altar boy being hit by a train.
mmm
Well these are all good, thought provoking choices so far. Great thread idea.
Now as much as I dislike country music, my emotional outburst song is Don’t Take The Girl by Tim McGraw.
The use of that phrase in so many different ways is brilliant. Each verse evokes an entirely new set of emotions. As a kid my father took me fishing often, and as a father and husband this really hits home. What you have could be lost in the blink of an eye - take nothing for granted.
Mitch Benn’s A Minute’s Noise For John
Probably meaningless if you didn’t grown up listening to John Peel, but if you did…
Every time I hear anything by Kid Rock I get nauseous, does that count?
I have to second Rod’s version of “The First Cut is the Deepest.” Just an unbelievable song/performance. Saw him do a live accoustic version at MSG in early 90s and it just blew me away forever. Unfortunately Crow’s version doesn’t do it for me–it’s not emotional or “deep” enough.
Also Jeff Buckley’s “Lover You Should’ve Come Over”
They work for me right now, when I’m no longer nursing a broken heart I’ll move on to something else.
A couple of people already mentioned “Cat’s in the Cradle”.
Gary Jules’ cover of “Mad World”. It’s a good example of how the performance really makes the song work (or not) - compare the cover to Tears for Fears’ original.
For me, Neil Young’s Powderfinger and Pink Floyd’s The Gunner’s Dream.
Fortunately, neither of them are ever played on the radio.
“Hurt” has made me cry since I was a preteen, both versions. Swearcuss.
This. (“Shiva” by The Antlers) I thought the first time I heard it that it was just a metaphor for how badly she’d cut him up emotionally, but then, almost out of nowhere, I realized- it’s a wish. He’s just found out his would-be wife is dead of bone cancer, and his dearest wish in the whole world is to take her place in that hospital bed so she can live. I sobbed for ages.
And though there’s no good version of it on the internet, the song “My Brother and the Pixie” by Vera Mesmer. Guy loves his little brother, worries about him, knows he has a habit of getting into trouble, wants to watch out for him, knows no one else will… And his brother wants nothing to do with him.
“Into the West”, from Return of the King. I first started listening to this as my father was in the hospital, dying of cancer. In spite of the message of the song, I can’t hear it without thinking that he’s gone, and I won’t get to talk to him ever again.
Along this vein is “Where Have You Been?”