 If you liked
Wolf's Rain OVA
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 ...then you might like
Kidou Senshi Gundam: Tekketsu no Orphans 2nd Season
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Gundam IBO and Wolf's Rain both have a heavy plot and one that seems like it could be tragic at first glance (one is a war story and the other is a post-apocalyptic anime so that's to be expected), but they still remain largely hopeful for most of their run time. But not in the sequels.
Both series are like a train here- continuously accelerating towards the final point, but then the train gets derailed somewhere in the middle and fall off the tracks due to a character decision or plot point. It continues speeding up and up towards the final colliding point without letting up
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Recommended by TadanoMari