Max Oppenheimer was an early collaborator of Egon Schiele’s and an Austrian Expressionist since the movement’s inception. Shortly after he was drawn to Berlin at the invitation of the art dealer Paul Cassirer, Oppenheimer informed his patron of his desire to make a portrait of his wife, Tilla Durieux. Cassirer was more than skeptical: “What? You want to paint my wife? Many have already tried that. [Lovis] Corinth and Max Slevogt and Stuck in Munich.” The painting process did indeed take a toll on the twenty-five-year-old, yet he managed to create a portrait, which came as a pleasant surprise to the art dealer. “I didn’t think you were capable of this,” said Cassirer – who seemingly held the portraiture of a “hideous beauty” as the greatest imaginable challenge. The famous actress is here endowed with a cool, repellent gaze and the placement of her hands is reminiscent of gestures found in Kokoschka’s works. Novel to Oppenheimer’s work at this point in his career, the background’s crystalline tissue evinces his venture into Cubism.