When I was younger and a bit more angsty, this song was my anthem.
Breathe Me by Sia never fails to get me. Instant emotional response, even before I saw the flash-forward sequence at the end of the Six Feet Under that used the track.
I also tend to get inexplicably sad when listening to *You Can’t Go Home Again *by DJ Shadow, not because the song itself is sad but because of when and where I was when I heard it the first couple of times, and my mind has gotten it all tangled up with good things coming to an end ever since.
I love the New Year’s season, if only because it means that Dan Fogelberg’s Same Old Lang Syne might be on the radio every now and then.
I really should just buy that one. It hits me hard in the gut just about every time.
edited for clarity
Way to go dude!
Unless of course you’re a woman… in which case, I’ll bet we have drastically different reasons for the song to cause weepiness.
BTW, I hope the Divorce Song line you used doesn’t too acurately reflect your feelings on the issues you’re dealing with.
Speaking of young and angsty, I remember playing Another Lonely Christamas over and over during a nasty stretch of my late teens.
I love the Ricki Lee Jones version of this song. She has such a sad quality to her voice.
Hey, don’t blame me, blame Harry! 
Breathe Me by Sia also gets to me every time.
Mad World, sung by Gary Jules at the end of Donnie Darko
This is slightly embarrassing, but Life’s a Show from Buffy the Musical
Song for Eric by Tori Amos:
I wait all day for my sailor
And sometimes he comes
See you over hill and dale
Riding on the wind I see
You know me
You know me like the nightingale
“Oh fair maiden I see you standing there”
Will you hold me for just a fair time
The tune is playing in the fair night
I see you in my dreams
Fair boy your eyes haunt me
Yep. I was trying to introduce my daughter to Walk Away Renee, (she’s 14 and loves 60s and 70s pop) and was sad to discover that Jones’ version is very hard to come by. The cassette we had is long gone, and the song isn’t on iTunes or (as far as I could tell) CD.
Love her take on that song.
My own favorite tearjerker is I Don’t Want To Hear It Anymore from “Dusty in Memphis”. It’s a Randy Newman song and he tempers the melodrama with ironic winks, but not so much as to take away the power …just enough that you can enjoy the glurge without guilt.
The young woman lives in a cheap thin-walled apartment and can hear the neighbors talking about how her man is stepping out on her.
*
Ain’t it sad, said the woman down the hall
That when a nice girl falls in love
Ain’t it just too bad that she had to fall
For a boy who doesn’t care for her at all?*
Tiptoe Ani DiFranco
It’s all of 37 seconds long…
Hoobastank- The Reason.
My friend’s first dance at her wedding…also the song played at her husband’s funeral less than a year later.
It makes me cry.
Was on the radio today at work and I had to go somewhere else until it was over.
At the end of a production of “The Heidi Chronicles” that I saw, the lead character sang “The Way You Look Tonight” to her new baby as a lullaby.
Ever since I had kids, thinking of that song in that context makes me tear up.
That’s easy. All you have to do is hear the Twisted Tunes version “Cat’s in the Kettle”. Now I can’t hear it without laughing.
“May It Be” by Enya. Every time I watch Lord of the Rings: The Fellowship and the credits start rolling, I bawl like a baby. It’s probably the worst one I can think of.
“Now We are Free” , Hans Zimmer. From the Gladiator soundtrack. Same as the damn Enya song, the credits start rolling and I go through half a box of kleenex.
“I can’t make you love me” by Bonnie Raitt.
“Rhapsody in Blue”, George Gershwin.
“Yesterday” by The Beatles
Mine is “Puff the Magic Dragon”. What of it, got something to say, wanna take it outside?
My genuine “Cat’s in the Cradle” story…when I was about 8 years old or so, and the song was everywhere on the radio, I loved the song. You see, my dad was seldom around, long hours, often cranky, and separation and divorce were in work. I misinterpreted the song as a happy and hopeful song, and thought it was celebrating my life as a kid and my relationship to my dad, since I actually thought I was rewarded and special for the odd minute scattered moments of happiness that my dad spared to give attention amidst all of the yelling, slamming, and general neglect. Lost in a vast desert, the smallest drop of water tastes like honey.
So I went up to him once while it was playing and said “This is my favorite song, it reminds me of us. I hope I’m a great dad, too, when I grow up.”
Though I didn’t understand why at the time, the bastard instantly turned white as a sheet–served him right. I bet he remembers that damn song! 
A Boy and his Frog by Tom Smith is the saddest song in the world. Ever. You can listen to it on his website here:
http://www.tomsmithonline.com/freestuff.htm
It’s the third mp3 in the list. He can’t even get all the way through singing it without choking up.
Damn you. 
Every time I manage to erase that song from my perception, someone has to drag it back again. 'Scuse me, I gotta go grab some Kleenex.
Hallelujah - the Jeff Buckley version - always gets me. I think it might have something to do with the fact that he died so young combined with the fact that the lyrics are just so beautiful and brilliant.
Reading the preface to the lyrics brings back a sad bit of humor that actually explains the song well. In an NPR interview of Jim Henson the audio was bad because the soundman miked the frog by mistake. What a Freudian tribute to Henson. He gave such life and personality to his characters. dammit.
The Verve The Drugs Don’t Work (about watching his father die of cancer - really sad and lovely melody too)
and so on…even just reading the lyrics gives me a lump in my throat.