Takehisa was born in the town of Oku, which has since been merged into the city of Setouchi in Okayama Prefecture, Japan.

[1] Takehisa's career doing illustrations began in June 1905 after he won a competition by the magazine Chugakusekai, owned by Hakubunkan, one of Japan's leading publishing companies.

After the High Treason Incident, a socialist-anarchist plot to assassinate Emperor Meiji in 1910, many of the people he worked with at the Heimin Shinbun were arrested and executed.

[1] He abandoned his direct support for socialist movements, but he maintained strong sense of sympathy to the struggles of the lower class throughout his life.

[1] Takehisa married Tamaki Kishi, a subject of many of his paintings and the manager of a Tokyo postcard shop, in 1907.

He documented the devastation of the disaster in a series of illustrations;[5] however, the earthquake ruined his business, and it was a setback he did not recover from for several years.

Takehisa left Japan to travel to the United States on 7 May 1931 during the decline of the Taisho Democracy and the rise of the militarist government.

[7] Seijun Suzuki's film Yumeji (1991), which forms the final part of his independently produced Taishō trilogy, is loosely based on the life of Takehisa.