We propose to demonstrate The Emotionally Aware Painting Fool, a novel system that combines a machine vision system able to recognise emotions with a non-photorealistic rendering (NPR) system to automatically produce portraits of the sitter in an emotionally enhanced style. During the demonstration, the vision system records a short video clip of a person showing a basic emotion. The system then analyses this video clip, locating facial features and tracking their motion. Using this tracking data, the system analyses which emotion was expressed and what the temporal dynamics of the expression were. This information is then passed to the NPR software. The detected emotion is used to choose appropriate (simulated) art materials, colour palettes, abstraction methods and painting styles, so that the rendered image may heighten the emotion being expressed. The live demonstration shows how each element of The Emotionally Aware Painting Fool functions and produces a portrait in approximately 7 minutes.