For me it's a tie between A Deepness in the Sky by Vernor Vinge and Look to Windward by Iain Banks. Although I do love a lot of the other books you guys have been bringing up - especially Ender's Game, Dune, Do Androids Dream of Electric Sheep, and The Moon is a Harsh Mistress... There's just...
I'm not entirely sure what you're looking for, but the best "mature" anime I've seen (that haven't been mentioned yet) are:
Moribito: Guardian of the Spirit
Set in a fantasy version of ancient Korea, the plot revolves around a famous female bodyguard who gets roped into protecting a cursed...
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