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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Megaman Battle Network 3: when [spoiler]Megaman sacrifices himself to save Lan D:[/spoiler] Click: when [spoiler]Adam Sandler starts chasing his kid after Sandler was hospitalized and would die... Then I got really really angry because I had started watching it midway through and didn't know it was a dream -_-#[/spoiler]