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After giving it some more thought the best example for me is Kingdom Hearts. It's a game that just shouldn't work and on many levels it doesn't, the controls can be slippery, the interface is clunky, your allies are often more of a liability than a help, and the story is just balls to the wall crazy; yet it's so damned charming I couldn't help but love every minute of it.

They way the story has progressed through the handheld versions has been a bit more off putting, as it's found ways to make an already inane story somehow more ludicrous, but it still hasn't managed to shatter my fondness for the series.