Trigun. Vash is just getting shit on for almost 2 centuries and all he's doing is trying to help humans, but his brother is just out to make him miserable.
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Grave of the Fireflies
Voices of a Distant Star. It tops Your Lie in April for me.
I came to say this. Holy hell it's brutal.
Something that had sad moments and I think is often overlooked is Gene of AI. It is more of a philosophical anthology series though rather than a show that builds up characters to hit you with emotional baggage.
A Place Further Than The Universe was so gorgeous oh lord. I was watching it on the exercise bike - big mistake - and was just openly sobbing at gym.
For my picks:
Shigatsu Wa Kimi No Uso or Your Lie In April is an absolutely heartbreaking story but its so beautiful. Strong contender.
Also Kimi No Na Wa or Your Name if movies count - I still cry like a baby every time I watch it, but it has a few of the story tropes that I'm an absolute sucker for so I'm biased. Its still incredibly moving even with that in mind.
I haven't seen a TON like I assume most on this comm have, but for me Grave of the Fireflies. It was too real for an animated film. Not in the sense that kids can't handle reality, but just in the fact that it's NON-STOP misery for the characters. There's literally never a high moment in the movie, just tragedy after tragedy happening to children.
And it even continues after the movie ends when you look it up. First you see that the lights on the movie poster are not fireflies but incendiary bombs and then you read further and learn that it's based on the real-life experiences of the author and was written as an apology to his dead sister. I mean it was his pride that led to her very slow and miserable death, so I can see him having problems coming to terms with that. It's a movie that just keeps on giving. I always say it's the best movie I only watch once.
Without knowing it was directly a true story about specific people, I knew it was more or less the truth for loads of unfortunate souls throughout history. Agreed on never watching it again.
Lot's of anime are sad but most of them end on a positive or hopeful note. That's why I consider anime that end on a bleak note to be sadder. Stuff like Grave of the Fireflies or the recent Look Back.
Bible Black.
The first 10-ish episodes of "To your eternity" has seriously fucked me up.
I cried for days.
Yeah agreed. The character building in that was good.
Madoka was pretty bleak at times.
Some might disagree, but I thought "Your Name" was sad.
Controversial
Clannad After Story, Liz and the Blue Bird, Phantom: Requiem for a Phantom, Violet Evergarden, A Silent Voice.
LOOK BACK was pretty dang sad, but it's one of the only 10/10 anime I've ever seen.
Dororo (2019) is also up there.
Damn I can't figure spoilers. Sora yori tooi was unexpectedly good
Ninja Scroll. I will never forgive that evil dude for permanently cock blocking the protagonist.
Other than Grave of the Fireflies, some others I never see mentioned are Saikano and In This Corner of the World.