Abstract: This paper presents an exploration of gestural and non-linear typography through the production of two software applications, TextDraw and TypeIs. Both were created through a media-art-research practice, wherein extended periods of development and artistic practice were exclusive of one another. This approach yielded applications which challenge contemporary typesetting methodologies, and produced new artistic works which exemplify gestural and non-linear typesetting techniques. This paper discusses the development of both software applications, the artworks made possible through their use, and situates the work within a history of experimental western typography in the 20th century.