In the beginning he tried to keep his neck above water-level with some odd jobs. Later from about 1875 on, he tried his luck as self-taught painter. He had met Charles Wirgman, an English painter, cartoonist and correspondant for a British newspaper in Yokohama. Kobayashi studied arts with him for a short period. He also met Shimooka Renjo, a photographer, from whom he learned the principles of photography.The Boston Museum of Fine Arts mounted an exhibition of late Meiji prints in 2001, and still has many such prints online. Among the most striking of Kobayashi's prints are:
From 1876 on Kobayashi Kiyochika created his first woodblock prints, scenes from Tokyo. Although his prints were basically kept in traditional Japanese style, [he] used Western elements like perspective, the effect of light and the graduations of shadows. By that time he probably had read about the French impressionists and seen photographs of their works in newspapers.
After 1880 [his] style became more traditional. He also turned to satirical cartoons and illustrations for newspapers and magazines. During the Sino-Japanese war the artist made about 80 war prints. War prints were like a last commercial resurgence of the old ukiyo-e business. Kobayashi's war prints are regarded as among the best in this genre - with a masterly play on the effects of light.
- Illustration of Lieutenant-General Yamaji Leading the Japanese Second Army during its Landing on the Jinzhou (Kinshu) Peninsula [Liaodong Peninsula]
- Illustration of Our Naval Forces in the Yellow Sea Firing at and Sinking Chinese Warships
- Illustration of the Second Army's Assault on Port Arthur
- Our Troops Landing in Taiwan in the Dead of Night
- The Army Advancing on the Ice to Attack Weihaiwei (Ikaiei)