Computational creativity is a new and developing field of artificial intelligence concerned with computational systems that either autonomously produce original and functional products, or that augment the ability of humans to do so. As the role of computers in our daily lives is continuing to expand, the need for such systems is becoming increasingly important. We introduce and document the development of a new “creative” system, called DARCI (Digital ARtist Communicating Intention), that is designed to autonomously create novel artistic images that convey linguistic concepts to the viewer. Within the scope of this work, the system becomes capable of creating non-photorealistic renderings of existing image compositions so that they convey the semantics of given adjectives. Ultimately, we show that DARCI is capable of producing surprising artifacts that are competitive, in some ways, with those produced by human artists. As with the development of any “creative” system, we are faced with the challenges of incorporating the philosophies of creativity into the design of the system, assessing the system's creativity, overcoming technical shortcomings of extant modern algorithms, and justifying the system within its creative domain (in this case, visual art). In meeting these challenges with DARCI, we demonstrate three broad contributions of the system: 1) the contribution to the field of computational creativity in the form of an original system, new approaches to achieving autonomy in creative systems, and new practical assessment methods; 2) the contribution to the field of computer vision in the form of new image features for affective image annotation and a new dataset; and 3) the contribution to the domain of visual art in the form of mutually beneficial collaborations and participation in several art galleries and exhibits.