Anything from the Escaflowne sound track T_T
http://members.lycos.co.uk/th8or/merle007.jpg
Little Merle has a voice that makes your tear ducts want to open for some reason... when she sings anyway...
this is one of those songs (link may be broken)

Probably barbars adagio -reminds me of Nam

Deep Inside of You by Third Eye Blind.
I pretty much love all of Third Eye Blind's songs, so every time I listen to them I pretty much feel like sobbing like a baby.
Probably has got something to do with what I associate them with, sorta like how songs can sometimes remind you of things or places where you first heard them, or where you were repeatedly exposed to them. They just take up a place in your head, triggered every time you listen to a song..and if that place is a sentimental memory..

<font color="yellow">"The Little Girl"</font> by John Michael Montgomery

<font color="yellow">"These New Shoes"</font> a Christmas-song by another country artist...can't remember who off the top of my head, but it will DEFINITELY make you cry.

the dutch national anthem makes me wanna cry of disgust, never heard any lyrics more stupid than that !

3 Libras by A Perfect Circle, has some sad/happy memories connected to it....

Forever Rachel, one of the themes from FF6, it's just so sad :(

Anything by eminem or macy grey makes me want to cry and then shoot myself.

My older brother used to break down in some serious tears back in the 60's whenever this played on the radio.

Cat's Cradle is the one about the Ireland Conflict, right? If not, ignore my next few lines, I'll only make a fool outta myself.

Being of Irish blood (but hey, I don't have the accent :)Cat's Cradle ALWAYS upset me. Strongly. I really broke down into tears whenever I heard it. I was severly saddened and depressed. :(

"One Last Cry" by Brian McKnight

"It Might Be You" by Steven Bishop

"3 Libras" by A Perfect Circle

"Movies" by Alien Ant Farm

"Once In A Lifetime" by Craig David

This depends on my mood... and if I hear some senti songs when I am really really depressed that could do.. but these make me sentimental and well you get the pic...