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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Anohana I was going through some things when I started watching it and I hadn't cried in years. I was a wreck that night. But felt good the next day. Also the sunflower scene from Clannad After Story killed me Ever since Anohana though I've been able to be more emotional and not feel weird about it.