Through the centuries, Taiwan became a transnational corridor, colonized and occupied by various cultures. In the nineteenth and twentieth centuries, the island moved from Qing Dynasty rule to Japanese occupation and then to Kuomintang Nationalist governance. Works created by Taiwanese artists living during this modern era display qualities that characterize this transnational context. One particular Taiwanese oil painter, Chen Cheng-po, was born during the last months of Qing Dynasty rule in Taiwan and was educated under Japanese domination. Like many artists in the region, Chen traveled to the Tokyo School of Fine Arts where he obtained two degrees before taking a teaching position in Shanghai, China. When violence broke out in China between Japanese and Chinese military troops, Chen returned home to Taiwan to continue teaching art until the end of his life when he was publicly executed by the Nationalist Kuomintang government who ruled after the end of the Japanese occupation in 1945. Chen’s works exhibit the artistic flavor of the three regions in which he lived, as well as depict the aesthetic characteristics of the Japanese occupation seen throughout the colonized region. In his paintings we see an artist aware of the crossroads of modernity in the artistic world and Chen’s life certainly attests to the transnational mobility that was characteristic of this area during the early twentieth century. These paintings reveal a talented artist wrestling with the various ideologies flowing through East Asia and the challenges of living as a colonial subject during a politically complex era.