The first film that I ever cried at was old even back when I first saw it as a child. "Captain's Courageous" with Spencer Tracey and Freddie Bartholemew. It was one of those old b/w movies they used to show every Sunday afternoon. I was inconsolable for hours after it finished. Up until then I used to laugh at my Mum and sister when they used to cry at films.
Some others that have made me cry are:
Gone with the Wind
Schindler's List
ET
Green Mile
Truly, Madly, Deeply
Mask
Sophie's Choice