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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Lone survivor Knowing its a true story and realizing what these guys do for each other. Then at the end they show photos of all the people that died in real life. It just hits you and you start bawling.