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Samurai X - Reflections ranks #1 for me as the saddest anime ever, but that's probably because I had spent over 90 episodes getting really attached to Kenshin and Kaoru (sp?) watching the much more light hearted Rurouni Kenshin series. After seeing all those episodes, the last thing I wanted to see was Kenshin and Kaoru grow sick and frail together in a much more serious-toned OVA. An anime has never made me cry before, but admittedly, I always come close when I watch the 2nd part to this OVA.
Gungrave ranks #2 for so many reasons. Anyone who hasn't seen this series should check it out. It's not for the lighthearted, but it's without a doubt the best anime I've ever seen.
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