Tears in Heaven by Eric Clapton... makes me think of my father who passed away.... brings tears to my eyes just writing the name....
Either THE KIDS or THE BED from Lou Reed's BERLIN CD.
Probably, What Makes a Man, Wherever You Will Go (especially the one by Charlen Soraia), Goodbye my Lover, or He Was Walking Her Home.
"And I don't want the world to see me cause I don't think that they'd understand when everything coming out broken i just want you to know who I am"Goo Goo Dolls-I'm Still Here
"The End of the Innocence," by Don Henley
The whole sound track to the movie The Dog of Flanders.
Strange Fruit by Billie Holiday
I'll Follow You Into the Dark - Death Cab for Cutie
I remember the exact moment I first heard it. I started crying because it was so beautifully sad.
This time of year, Sarah Mclachlan, Wintersong, beautiful song but makes me cry, otherwise duno, loads of sad ones but depends on mood at the time
Time To Say Goodbye ~ Sarah Brightman
http://www.youtube.com/watch?v=oNvFPKujc5w&feature=related supposedly this is
Scarlet Ribbons by Sinead O' Connor. It makes me feel a very deep sadness, my eyes nearly always well up when I hear it.
Most of the sad songs I've heard were accompanied by video that made them sadder, like Don't Be Afraid, You're Already Dead in World's Greatest Dad, or the music to the Dead Island trailer.
D-I-V-O-R-C-E by Tammy Wynette