Kiyochika Kobayashi started out creating caricatures and humorous illustrations after his meeting with Charles Wirgman, journalist of the London Illustrated News and founder of the satirical periodical Japan Punch. From 1876 to 1881 Kobayashi created a succession of engravings about everyday Tokyo life, 'Kosenga'. This series was followed by a historic series (1882-1893) and a series of paintings dealing with the conflicts of Japan with Russia and China (1894-1905).
At the same time he made numerous illustrations published in magazines such as Maru Maruchinbun, Shinban Sanju ni Menso and Kyoiku Iroha Tango. In 1894 he founded his own school, Kiyochika Gajuku.