I don't really cry, which I view as a deficiency in myself. However, there are a few songs that are emotionally loaded for me.
When I got the news that my grandmother had died, I locked myself in a room to be alone. I decided to play the soundtrack to The Royal Tanenbaums
On that album there is a song by Nick Drake called "Fly."
Nick Drake's a pretty depressing guy at the best of times, but some of the lyrics in this song really hit me and helped me through a tough night.
"Please give me a second grace,
Please give me a second face,
I've fallen far down, the first time around,
Now I just sit on the ground in your way"
I can't really hear that song without being reminded of that tough night.