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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Non-spoiler: there's an unexpected death at the end of Ong Bak that probably shouldn't make the average person cry, but they were such a great character that it seemed like a much more dramatic loss to me. [spoiler]I actually cried right at the end, when Ai Hum Lae died. He went through so much shit through that whole movie, all he ever tried to do was make it rich and live an easy life. He didn't have the most legal ways of working, but he was the only character with a good sense of humor, too. I got the same feeling from Jackie Ma's death at the end of Sleeping Dogs. [/spoiler]