Kokoschka's early career was marked by intense portraits of Viennese celebrities. He served in the Austrian army in World War I and was wounded. At the hospital, the doctors decided that he was mentally unstable as well as physically wounded. Nevertheless, he continued to develop his career as an artist, travelling across Europe and painting the landcapes he encountered. He had a passionate, often stormy affair with Alma Mahler, shortly after the death of her infant daughter and her affair with Walter Gropius. After several years together, Mahler rejected him, explaining that she was afraid of being too overcome with passion. He continued to love her his entire life, and one of his greatest works Bride of the Wind is a tribute to her.

Deemed a degenerate by the Nazis, Kokoschka fled Austria in 1934 for Czechoslovakia (Prague). There he employed the Oskar-Kokoschka-Bund with other fled artists. In 1938 when the Czechs began to mobilise for the expected invasion of the Wehrmacht, he fled to the United Kingdom and remained there during the war. All members of the OKB where escaped through Poland and Sweden with help from the (British Committee for Refugees from Czechoslovakia, later the Czech Refugee Trust Fund). He became a British citizen in 1946 and only in his last years would regain Austrian citizenship. He travelled briefly to the United States in 1947 before settling in Switzerland, where he lived the rest of his life.