Oskar Kokoschka CBE (1 March 1886 – 22 February 1980) was an Austrian artist, poet, playwright and teacher, best known for his intense expressionistic portraits and landscapes, as well as his theories on vision that influenced the Viennese Expressionist movement.

The second child of Gustav Josef Kokoschka, a goldsmith, and Maria Romana Kokoschka (née Loidl), Oskar Kokoschka was born in Pöchlarn. He had a sister, Berta, born in 1889; a brother, Bohuslav, born in 1892; and an elder brother who died in infancy. Oskar had a strong belief in omens, spurred by a story of a fire breaking out in Pöchlarn shortly after his mother gave birth to him.^{[citation needed]} The family's life was not easy, largely due to a lack of financial stability of his father. They constantly moved into smaller flats, farther and farther from the thriving centre of the town. Concluding that his father was inadequate, Kokoschka drew closer to his mother; and seeing himself as the head of the household, he continued to support his family when he gained financial independence. Kokoschka entered a Realschule in 1897, a type of secondary school, where emphasis was placed on the study of modern subjects such as the sciences and language. Despite his intent of continuing a formal education in chemistry, Kokoschka was not interested in such subjects, as he only excelled in art, and spent most of his time reading classic literature during his lessons. Like many of Kokoschka's French and German contemporaries, he was interested in the primitive and exotic art featured in the ethnographical exhibits around Europe.

One of Kokoschka's teachers suggested he pursue a career in the fine arts after being impressed by some of his drawings. Against his father's will, Kokoschka applied to the Kunstgewerbeschule in Vienna, now the University of Applied Arts Vienna. He received a scholarship and was one of few applicants to be accepted. The Vienna Kunstgewerbeschule was a progressive school of applied arts that focused mainly on architecture, furniture, crafts, and modern design. Unlike the more prestigious and traditional Academy of Fine Arts Vienna, the Kunstgewerbeschule was dominated by instructors of the Vienna Secession. Kokoschka studied there from 1904 to 1909 and was influenced by his teacher Carl Otto Czeschka in developing an original style.

Among Kokoschka's early works were gesture drawings of children, which portrayed them as awkward and corpse-like. Kokoschka had no formal training in painting and so approached the medium without regard to the "traditional" or "correct" way to paint. The teachers at the Kunstgewerbeschule helped Kokoschka gain opportunities through the Wiener Werkstätte or Viennese Workshops. Kokoschka's first commissions were postcards and drawings for children. Later, Kokoschka said that this exercise provided "the basis of [his] artistic training". His early career was marked by portraits of Viennese celebrities, painted in a nervously animated style.

Following his own artistic training, Kokoschka dedicated years of his life thereafter teaching art and writing articles and speeches documenting his views and practices as an educator. 17th-century Czech humanist and education reformer, Jan Amos Comenius, was Kokoschka’s primary influence in terms of how to approach education. From Comenius’s theories, Kokoschka adopted the belief that students benefit most from using their five senses to facilitate reasoning. Kokoschka taught in Vienna from 1911 to 1913 and then again in Dresden from 1919 to 1923. While his efforts as a teacher were noted in various publications, they generally focused on his personality captured within his own art rather than his classroom practices. Kokoschka neglected the conventional structured methodologies and theories assumed by art educators, and instead taught through storytelling infused with mythological themes and dramatic emotion. In 1912, Kokoschka delivered his essay “Von der Natur der Gesichte” (“On the Nature of Visions”) at the Akademischen Verband für Literatur und Musik in Vienna. This essay outlined Kokoschka’s artistic conceptualization about the relationship between inner vision and optical sight. In considering his own art, Kokoschka expressed that inspiration stemmed from daily observations that he collected optically while engaging with his contemporary surroundings. Kokoschka’s ability to acknowledge how these stimulations manifested within his inner imagination resulted in works that draw upon the subconscious rather than optical vision. Further, Kokoschka granted the viewer with the task of interpreting the image based upon how they experience the vision within their own realm of consciousness. This concept, in congruency with Wassily Kandinsky’s theory pertaining to spirituality in art, has become the basis for which art historians understand Viennese Expressionism.

In 1908 Kokoschka was offered the opportunity of submitting works to the first Vienna Kunstschau. This government funded exhibition was established to both bring in tourists and affirm Vienna's prominence within the art world. Kokoschka received a commission from the Director of the Wiener Werkstätte, Fritz Wärndorfer, for color images that would supplement a children’s book and be displayed at the exhibition. Kokoschka, however, took the liberty of producing images that would serve as illustrations to the poem he wrote a year earlier, Die träumenden Knaben (The Dreaming Youths), which took on the form of an autobiographical adolescent fantasy that was inappropriate for a young audience. In his autobiography, Kokoschka explained the origins of the poem, which follow his personal experience as a young student who was in love with his Swedish classmate, Lilith. Die träumenden Knaben consists of introductory pages with two small black and white lithographs, in addition to eight larger color lithographs with a vertical column of text positioned beside each image. Influenced by the compositions found in medieval art, Kokoschka depicted various moments in time simultaneously within each individual image. Kokoschka also adopted the bold lines and expressive colors of traditional European folk art and juxtaposed them with the stylized ornamentation and two-dimensional bodies of Jugendstil. The final page, titled Das Mädchen Li und ich (the Girl Li and I), features the angular forms of the young boy (Kokoschka) and girl (Lilith), taking on the style of the Belgian sculptor George Minne. This work, which Kokoschka dedicated to his former teacher Gustav Klimt, demonstrates the transition from Jugendstil to Expressionism.

Die träumenden Knaben along with the tapestry titled The Dream Bearers, which is now lost, were the first works ever to be exhibited by Kokoschka. Like the book illustrations, Kokoschka’s tapestry was considered disturbing due to its depiction of youthful, exotic and sexualized fantasies. Upon showing these two works, Kokoschka was subject to a backlash from conservative officials and only a small proportion of the five hundred copies of Die träumenden Knaben were actually bound and sold. As a result, he was expelled from the Kunstgewerbeschule and found his place within the Viennese avant-garde. Austrian architect Adolf Loos befriended Kokoschka and introduced him to other avant-garde members who then became his subjects in a series of portrait paintings.

Kokoschka painted a bulk of his portraiture between 1909 and 1914. Unlike many of his contemporaries who were also receiving portrait commissions, such as Edvard Munch, Kokoschka maintained complete artistic freedom because they were generally not ordered directly by the sitter. A majority of Kokoschka’s subjects were clients of the architect Loos, and it was Loos who ordered the portraits and agreed to purchase them if the sitter chose not to. Other portraits by Kokoschka feature friends and advocates within his circle who supported the modern art of this period. Prominent members of this group who had their portraits painted include the art dealer Herwarth Walden, art supporter Lotte Franzos, poet Peter Altenberg, and art historians Hans and Erica Tietze.