Holycrap! I missed that news.
Let me offer a belated congratulations.
Also, please alow me offer three songs that are (surely?) impossible to cry to:
Paul Kelly, I’ve Done All the Dumb Things
Men At Work, Land Down Under
GuyzNite, Die Hard
A couple of songs that cause extreme wistfulness for me are Don Henley’s Boys of Summer and* Hackensack* by Fountains of Wayne.
Every time I hear this song, I think of the time I was tramping across Belgium, feeling like a stranger in a strange land, wanting nothing more than to meet a friendly or familiar face. I found myself one day in a humble boulangerie, hoping against hope that I wasn’t going to have to try to order in Flemish. Screwing up my courage, I asked the hulking proprietor if he spoke English. Without a word of reply, he cheerfully handed me a treat that reminded me of home.
Since then, I get misty whenever I hear “Down Under.” 
That is so frickin awesome.
Snort (-ing illicit substances in a den in Bombay)
Bridge Over Troubled Water and The Boxer by Simon and Garfunkle. I hadn’t heard either in years and I was driving and listening to someone’s CD. I had to pull over after a while and just let it all out. There’s a youtube song from the Andy Williams show, with S&G and Andy singing Parsley Sage Rosemary and Thyme, and it is so heavenly beautiful I could cry from the sheer beauty.
Shelley West and David Frizzell’s “You’re the Reason God Made Oklahoma”.
My wife’s nomination: Don Williams’ “Good Ole Boys Like Me”
Kid Rock & Sheryl Crow Picture
Simon & Garfunkel, Kathy’s Song, For Emily, Wherever I May Find Her.
Bob Dylan, Girl From The North Country. One too many mornings.
Depends on my mood and the amount of beer intake, a few would be,
“The world I know” - Collective Soul
“Ordinary world” - Duran Duran
“Listen to your heart” - DHT
“Mad World” by anyone.
“Let Me Down Easy” by Little Milton. Blues to the max. I should know.
Stand By Me by Mr. Ben E. King. I can only wish - hope - someone will be standing by ME, at the end. (I don’t think so, I think I’m going to exit this life alone with an occasional look-in by strangers. And that makes me cry harder.)
Good god. I don’t know how to link to a YouTube video, but “Hero” by Mr. Children just guts me every single time. It’s clay animation. The lyrics are in Japanese, but I think the sadness comes across even without them–though they do crank it up another six notches. Gawd, why the hell did I go dig that one up?
Not Carlson…Thanks for your kind reply. I am quite "over it " but those songs DO remind me of the initial pain a bit. Life isn’t easy sometimes, that’s for sure! I will definately look for the thousand wonderful things…here’s to you getting a thousand great bouts of happiness too.
Jeff Buckley’s version of Hallelujah
My mom never got hers diagnosed or treated, so when it finally caught up to her she died after a couple of weeks of severe pain. In the disbelieving time after (which persists four years later), I listened to Emmylou Harris duets while finishing a quilt Mom started, and the one that gets me is Gulf Coast Highway, by Emmylou and Willie Nelson.
“And when she dies she says she’ll catch some blackbird’s wing
And she will fly away to heaven
Come some sweet blue bonnet spring”
Emmylou Harris has that wistfulness that would make me cry if she sang the phone book, so forget it with lyrics like that!
For me, it’s The Mountain Goats’ Matthew 25:21—it’s a very simple, unadorned, down to the bones telling of that impossible situation of watching a loved one die.
It’s been ten years since I held my own mother’s hand as she lost the fight against cancer. I try to get through it every now and then, such as just now—as it turns out, I’m not ready.
You were a presence full of light upon this earth
and I am a witness to your life and to its worth
I’m so sorry. The only thing I can think of is I wouldn’t be so sad if she hadn’t been so great and I hadn’t loved her so much – and that makes it worth it. I’m glad I had her for as long as I did but truthfully, the first thing I thought when I heard she was dying was “I have to live for forty more years without my mom?!”
She asked for How Great Thou Art at her funeral and that has a tearjerker verse for me:
When Christ shall come with shout of acclamation
And take me home
What joy shall fill my heart.
Then I will bow in humble adoration
and there proclaim, my God, how great Thou art!
And In Paradisum:
May angels lead you into paradise; upon your arrival, may the martyrs receive you and lead you to the holy city of Jerusalem. May the ranks of angels receive you, and with Lazarus, once a poor man, may you have eternal rest.
First off, I second “The Green Fields of France” and “Kilkelly, Ireland.” It’s even worse once you realize the latter was based off a real series of letters.
Second, Harry Chapin’s “Taxi”. I’m specifically thinking about the chorus:
You see, she was gonna be an actress
And I was gonna learn to fly
She took off to find the footlights
And I took off for the sky.
And then that last stanza just twists the knife in . . .
I’ve posted this on the SDMB before, but for some strange reason I find the acoustic version of “While My Guitar Gently Weeps” so. damn. sad. It has a completely different tone to the version on the White Album - I find it much more . . . sincere? Heartfelt? I don’t know, but I go misty-eyed.
Recently a much-loved relative of mine died - shortly afterwards, we were listening to Leonard Cohen’s “Hey, That’s No Way to Say Goodbye,” and we just broke down. Leonard Cohen has a talent for depressing music - “Chelsea Hotel No. 2” (written about Janis Joplin shortly after her death), is also beautiful.
Lastly, there’s tons of Paul Simon - both with and without Garfunkel - that’s heartbreaking. Despite the fact that the lyrics really aren’t all that sad (at least, compared with some other songs of his), I was listening to the acoustic demo of “Take Me to the Mardi Gras” lying in bed late one night and something resonated. And I will lay my burden down/Rest my head upon that shore/And when I wear that starry crown/I won’t be wanting anymore . . .