And all I do is miss you and the way we used to be
All I do is keep the beat, the bad company
All I do is kiss you through the bars of a rhyme
Juliet, I’d do the stars with you any time
Juliet, when we made love you used to cry
You said, “I love you like the stars above, I’ll love you 'til I die.”
There’s a place for us, you know the movie song
When you gonna realize it was just that the time was wrong, Juliet?
Since I Fell For You - Lenny Welch (the version I know) - one of the finest most heartfelt sad songs ever written. ‘…you made me leave my happy home…you took my love and now you’re gone…since I fell for you…’
Sara - Stevie Nicks - I went through a devastating breakup when this song was on the radio, so, I associate it with agonizing sadness. I always picture a little white bird bravely flying through dark rain clouds.
“I’ve Been To Town”, Glenn Yarbrough. I heard this in the midst of a very bad breakup and it nearly made me suicidal.
Don’t tell me any more lies,
I can’t waste any more years,
I’ve seen my image in your eyes,
Dissolve in disappointed tears.
Fucking hell, man.
You Can’t Go Home Again (Nanci Griffith) for personal reasons.
This ol’ town never did really care that much for me.
I don’t know why I always come here in my dreams.
Ah, Austin.
And Southbound Train (Nanci Griffith).
Some things I know
Some things I guess
Some things I wish that I could learn
To express
Like the way that I feel
As I stare at the sky
And I remember your voice
And the sound, of goodbye
“Tears in Heaven” probably would have been just another sappy song to me if it hadn’t come out around the time my Grandma died.
For me, the answer is “Keep Me in Your Heart” by Warren Zevon. There was a year when death seemed to be following me around. My infant son died (still birth), then my dad (unexpected), a dear coworker and friend (after a long illness), and my grandmother all died in about an eighteen month period.
I don’t remember when during this time I saw the video of this version of the song, but I just couldn’t get it out of my head. It must have been shortly before my dad’s funeral, because I remember going to Walmart right then and buying the CD (before I had an iTunes account and all that). I had the song played at my dad’s funeral.
I think that’s an expected gut punch. If that song doesn’t punch you in the gut you’re dead inside.
“Dick and Jane” by Bobby Vinton. I listen to it every year or so. Lame song, but the theme just hits me like a lead anvil. That person you think you’ll eventually end up with…and then she’s gone, and it’s too late. Damn.
I Can’t Make You Love Me by Bonnie Raitt reminds me when I was dead-gone in love with a boy who liked me well enough, but he didn’t love me. It was a horrible, horrible ache to realize it, and this song brings it back.
Go Rest High on that Mountain makes me feel viscerally every death I’ve ever had to endure. I don’t connect it to any one loss, but listening to it, and knowing the deaths Vince Gill was writing about it, always makes me tear up. Also it’s a beautiful song.
Damn you all picked some good ones including the Moody Blues one
Peter Gabriel’s cover of Book of Love and The Power of the Heart
Ugh that last one…here comes the “rain”
Wow. Very moving, thanks for sharing.
Oh man. I was watching “Funny People” and Seth Rogen makes a mix for Adam Sandler who thinks be dying. Something light was on and then it switched to Keep Me In Your Heart. 
It was a sucker punch in the middle of the movie, not expecting that at all.
If I leave you it doesn’t mean I love you any less
Keep me in your heart for a while
::sob
Another mourning one is Darlin’ Kate, for Kate McGarrigle:
For we’ve all known down here,
The taste of joy and strife
You were the sweetest note
In the chord of life.
As you slip the surly bonds of earth
And sail away
Perhaps we will meet again
Somehow, some day
Until then, there’s nothing we can do but wait,
To see once more,
Our darling Kate
Damnit i mean Here comes the ‘flood’.
Since my daughter died there are some obvious ones: Jane Siberry’s “It Cant’ Rain All the Time”, Sarah Maclachlan’s “Angel” and Andy Williams’ “Gone Away”* spring to mind.
But this is about unexpected. One time on the radio I heard Macy Gray’s “I Try” and it was like a fist to the gut and I just couldn’t stop crying.
How could I forget:
Art Garfunkel singing, “Bright Eyes,” (from Watership Down)…I’ll have to leave the room. Or, at least, stop the vid.
Maybe not “unexpected”, but: When I Was Your Man by Bruno Mars.
Too real, Bruno…
Ugh. Good one.
As a general rule Burt Bacharach is good for this
or here’s Stings When We Dance
OR Stings They Dance Alone about widows or mothers who lost husbands and sons to Pinochet.
Hmmm, yeah. I kinda missed that important word. I will say, though, that the first time I heard this song, I wasn’t expecting it.
George Jones, ‘He stopped loving her today’…not a big George fan but that song is just so sad.
When Vince Gill sang at a concert for Jones after he died and he sang 'Go rest high on that mountain ’ and he cried halfway through the song. The lady singing with him , I think it was Patti Smith, kept having to carry him. It was a tear jerker.
“I Want To Know What Love Is” by Foreigner.
That damn song once caused me to burst into tears in the middle of Value Village, of all places!