Kuniyoshi was born on September 1, 1889 in Okayama, Japan. He immigrated to the United States in 1906, choosing not to attend military school in Japan. Kuniyoshi originally intended to study English and return to Japan to work as a translator. He spent some time in Seattle, before enrolling at the Los Angeles School of Art and Design. Kuniyoshi spent three years in Los Angeles, discovering his love for the arts. He then moved to New York City to pursue an art career. Kuniyoshi studied briefly at the National Academy and at the Independent School in New York City, and then studied under Kenneth Hayes Miller at the Art Students League of New York. He married his first wife Katherine Schmidt, who in 1919 lost her American citizenship due to her relationship with Kuniyoshi who was ineligible for American citizenship. He later taught at the Art Students League of New York in New York City and in Woodstock, New York. Nan Lurie was among his students, as was Irene Krugman. Around 1930, the artist built a home and studio on Ohayo Mountain Road in Woodstock. He was an active member of the artistic community there for the rest of his life. One of his pupils from the League, Anne Helioff, would go on to work with him at Woodstock.