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This movie has always been a whimsical train wreck for me. I initially assumed it was his last since it indicated a weird loss of perspective and economy in his work, though he mostly recovered with Ponyo. Even that last film feels like a shadow of his previous work, though. I wasn't very surprised when he eventually announced his retirement and I still have misgivings about his surprise "return."
It's been a little while, but reading the book this is based on i seem to remember answers some of the questions. Which doesn't excuse the film - although I must say I always enjoy films where everything is not explained. Where does Howl go? Well, in the book it turns out he also lives as a teenage boy. In Wales. Yeah.