"I Wish You Peace" by the Eagles when I was 16 and my first boyfriend ran away to join the circus without telling me he was leaving...we had been together for a whole year and it hurt that he just disappeared like that. *sniff* He made a great clown.
"Cat's In The Cradle" by Harry Chapin when I listen hard and really feel the story.
"How Am I Supposed To Live Without You" by Michael Bolten...that one really got to me as I got older and older, having spent nearly my whole life loving a man from a distance for the most part and up close and personal during the best days of my life. Glad I got over that one!
I can't think of any song that has made me cry or even feel like it for the last seven years or so...I probably just don't listen as closely as I used to, I know I don't listen nearly as much anymore, esp since the radio in my car died. Its been harsh but I am almost used to it now.