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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La vita è bella (Life Is Beautiful). I'm not going to spoil it for anyone but the movie is about a Jewish book keeper named Guido in Italy who gets married, has a son and Guido and family are thrown into the German [url=http://www.wikipedia.org/wiki/Godwin%27s_law]-godwinslaw!-[/url] camp. Throughout the horrific events of the Holocaust, Guido trys to protect the innocence of his son and tells him that this is all a game and the grand prize for surviving is a tank. Despite my terrible short summery of the movie, I HIGHLY recommend it. It's funny, it's gut wrenching, and it's the only movie that made me bawl like an idiot.