Call me sick, but I found A Clockwork Orange, while full of poignant social commentary even in this day and age, to be one of the funniest black comedies ever filmed. The multitude of mini-satires in that film just kill me.
As far as movies that just bring me to my knees everytime, just about anything with a self sacraficing hero in it will make me ball like a baby. Schindlers List, Braveheart, Saving Private Ryan, Gladiator, etc etc.... If there ever were men and women of this caliber in life, they sure aren't around any longer, and that gets to me everytime.
A couple of love stories wreck me too, like When A Man Loves A Woman and Hope Floats. Ok, so I am a puss, sue me