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Yamashita was born in Asakusa, Tokyo. At the age of three, he suffered an acute abdominal disorder which, although not life threatening, left him with a mild speech impediment and some neurological damage.

At elementary school, Yamashita was the victim of bullying and on one occasion wounded a classmate with a knife. Because of this, his parents decided to move him to the Yahata institution for the mentally handicapped in Ichikawa, Chiba. It was here he started to experiment using torn pieces of paper to create pictures. His talent was recognised by mental health expert Ryuzaburo Shikiba, who organised an exhibition of Yamashita’s work in Osaka which received wide praise.

Tiring of life at the institution, and in order to avoid the mandatory physical examination for recruitment into the Imperial Japanese Army, Yamashita ran away in 1940 to start his wandering around Japan, which would last until 1954.

At the age of 21, staff from the institution found him helping in a restaurant and forced him to take the recruitment exam. Eventually he was considered exempt from service. The events from this time were recorded in his “Wandering Diary” of 1956, and the most popular image of Yamashita travelling alone through the country with his rucksack comes from this period.

Yamashita used the Chigiri-e method of sticking torn pieces of coloured paper together to depict the scenery he saw on his travels, and some of his most famous works such as “Nagaoka no hanabi" and "Sakurajima" were made in this way. Possessing eidetic memory, Yamashita usually recreated the entire scene from memory when he returned to the institution or his home. Because of this, Yamashita is often considered an autistic savant.

In the post-war period, he became widely known as the “Japanese Van Gogh” or the “Naked General” (due to his habit of wearing only a vest during his travels). In 1956, the Kiyoshi Yamashita Exhibition opened at the Daimaru store in Tokyo, and toured the country, stopping at 130 places in Japan and attracting over 500,000 visitors. In June 1961, Yamashita and Shikiba embarked on a 40 day tour of Europe. Here he recorded the many famous places and monuments he saw.