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Pyuupiru is a Japanese contemporary artist whose works are highly acclaimed in recent years. An old friend of his (hers), Daishi Matsunaga has filmed him for 8 years, ever since Pyuupiru frequented clubs wearing eccentric handmade costumes. Pyuupiru went through a gender identity disorder, broken heart and castration operation, and then he held a performance at Yokohama Triennale in 2005 as a compilation of his life experience. Pyuupiru was born as male, but he gradually realized that his body does not fit him. He tried to clear that feeling by wearing those eccentric costumes. In a short while, people started to take notice of it as pieces of art, and he started creative activity in the contemporary art world. This documentary film 'PYUUPIRU 2001-2008' follows the vicissitudes of his mind, body, and the art works that he gave birth to. Enormous amount of footage also reveals the relationships with his family, friends and his boyfriend who have always watched him with a warm look, although they had mixed feeling for the reality.