This includes tv shows and books as well.
When I was 8 I cried during the originial transformers movie (1986) when optimus died, maximum sadness above.
Also, in the Walking dead
[spoiler] I teared up quite a bit when carl had to shoot his own mother in the head to prevent her from turning. Such an emotional scene *sobs* [/spoiler]
What has made you experience the deep well of sadness?
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Sonic X the very end. Those who have seen it will know what I'm talking about. I cried at the end of Spice and Wolf. Amazing anime, the end was FAR too soon. Let's see.. I cried whilst reading The Kitchen House, an excellent piece of American literature about a white child adopted into a black family. To Kill a Mockingbird. The book AND the movie. That's all I can think of.