Kissing You by Desiree.
Circle Game by Joni Mitchell.
and many others…
I thought of a few more…
Ashes of San Miguel by Roger Clyne and the Peacemakers
Full lyrics here, because really… the whole song is amazing. It’s about a guy taking a trip to Hermosillo with his best friends ashes riding shotgun in the car. He talks about what it was like when they used to make the trip together and it just really captures the bleak Mexican landscape and the hollowness of losing a friend. Even reading the lyrics makes me choke up.
Far Behind by Candlebox
Dante’s Prayer by Loreena McKennitt
Now if you’ll excuse me, I’m going to fill my iPod with emotional masochism thanks to this thread. 
Oh sweet merciful christ, I forgot about this one. My mom started singing this song to me when I was a baby and its still her favorite piece to break out the guitar to when we spend too much time together. :smack:
I used to think it was great when I was a kid, but now that my own child is somewhere between skating over ten clear frozen streams and cartwheels turning to carwheels, the song absolutely* kills me*.
I have no idea how my mom sings it without bursting into tears halfway into the first verse. Urrgh.
“Let Love In” by Goo Goo Dolls.
Into the West by Annie Lennox hits me hard every time.
Herbert Grönemeyer has a song, Mensch, which always brings the conversation in the car to an instant halt and has us bumping each other’s hands as we reach for the volume knob to turn it up. He wrote this after losing his wife and his brother within a short time of each other. The song is so full of acceptance and understanding of what it means to be human, with such a poignant undertone of loss and longing … hey, who’s got the tissues?
I’m a devout athiest, but damn if XTC’s ‘Dear God’ doesn’t break me down all the time.
The Ballad of John Henry’s Hammer by Johnny Cash.
Reminds me of tough old men whom the world outgrew. Specifically, of my grandpa. The line “this is the first time I’ve watched the sun come up that I couldn’t come up with it” just tears me to shreds.
I’ll make it three for Puff the Magic Dragon. It just kills me when little Jackie Paper grows up and Puff loses his lifelong friend.
Another song that brings a tear to my eye is Brook Benton’s version of Tony Joe White’s Rainy Night in Georgia. That voice and those lyrics move me.
Oh my god, fourthed. My dad used to play this on the guitar and I would get all choked up every time!
Also, Adam’s Song by Blink-182. The line “Please tell Mom this is not her fault.” KILLS me.
Most songs that make me cry don’t embarrass me, because I feel like you’d have to be made of stone not to cry at them.
But since my fiancee broke up with me in March, I have had real issues with the song “That Was Yesterday” by Foreigner (and lest you think, “Why would she ever hear that song? It’s not the 80s anymore,” my parents are big Foreigner fans and have been frequently playing the live CD they got when they saw them live recently.)
I can usually get through it, until this part:
But that was yesterday
Love was torn from my hands
But it’s not the end of my world
Just a little hard to understand…
It just kills me, because she broke up with me and never explained why, and I still don’t understand and maybe never will.
And, if that part doesn’t get me, the end does:
Goodbye yesterday
Now it’s over and gone
But I hope somewhere deep in your heart
yesterday will live on…
I guess I feel embarrassed because it’s an overblown 80s song, and it’s not an obvious tearjerker…it makes me cry because something specific that happened to me, not because of some more generalized experience. 
Ave Maria Schubert
I Would Give Anything Bread
The Wreck of the Edmund Fitzgerald Gordon Lightfoot
Wharf Rat The Grateful Dead
A lot of great choices here.
Yep, me too. I always take the time to reflect about my country and all the brave members of our armed forces currently serving where ever they are, and then there’s tears. But maybe this isn’t “embarrassingly weepy,” given the song, hey?
*Hey Jupiter *by Tori Amos
It’s not embarrassing because I’m not likely to hear it in public.
The Jane song that destroys me is “The Valley” ever since I saw Jane perform it with Tim Ray on piano at the Orchid Room. She introduced it talking about her grandmother’s death, and the relationship of the song to the Lord’s Prayer. I can’t even think about that without getting a lump in my throat, goosebumps and misty eyes. Probably the most intense single concert experience I’ve ever had.
Kirsty MacColl’s “Angel”, doubly so now that she’s gone.
Several Randy Newman songs: “Texas Girl at the Funeral of Her Father”, “Jesse’s Song”, “Marie”…basically I’m just a total sap for his songwriting. Hell, I’m a giant weepy sap in general.
Yep, that’s the one.
<sob>
I mean, really, WTH?
<sniff>
<wipes a tear>
<sob>
I hate that fucking song. Especially when the kleenex box is empty.
<sniff>
<rinse repeat>
I’m sorry and I swear I mean no disrespect, but I can’t stop laughing at the idea of someone crying as the result of a song by the Goo Goo Dolls. Granted I was already laughing at the person who posted Candlebox lyrics.
At Seventeen by Janis Ian
Blowin’ in the Wind by Bob Dylan
Strange Fruit by Billy Holiday
I can’t listen to even a third of I’m Going to Go Back There Someday. What is shameful is that it is sung by a MUPPET, and that muppet is GONZO, and I can’t help it. My amazing, strong, pillar of a brother had a very traumatic experience when we lived in Peru and he used to sing this to himself and to me thinking about when we would move back to the U.S.
My heart breaks for him and I’m crying just from the first four bars of the intro. I’ll forever associate that song with that experience.
Alone by Heart.
Just had dinner and was flipping through my iPod:
Warren Zevon - “Keep Me In Your Heart”. It would be sad and moving even if he was still alive, but being written by a man facing death with courage and humor - it’s devistating. I could go on but I’m worried about shorting out my keyboard.
Kate Bush “The Ninth Wave”. A bit of a cheat, as it’s not one song by an album side long song suite. It’s a journey through death and rebirth and I’ve not been able to listen to the whole thing since my Mom died. If I have to select one song, it’s the last one, “The Morning Fog”.