In this thesis I explore the role and significance of editorial illustration, developed in printed publications and evolving within online publishing structures. Editorial illustration has a long tradition of illustrating stories in news publications, but I argue that in current online news websites its particular role has all but failed. Online publishing has become the driving force within editorial publishing and this raises the question whether, and how, editorial illustration can continue to be a successful constituent in an online publishing environment? I argue that the continuation of editorial illustration lies within digitally native narrative forms, from online interactive documentaries, game-based storytelling, data-visualisation to memes: viral images spread through social media. Within these forms the significance and agency of illustration is not only clearly present but evolving, except here illustration is interwoven with the story. I argue that these forms of illustration, as well as printed illustration, are based on the same conceptual model and articulate editorial illustration’s inherent attributes. I propose a constellation of four attributes (manifestation, translation, reflection, and engagement) that together give rise to the key quality that illustration offers to the reader, deliberation. Illustration should not be understood as a separate artifact, positioned next to a text, but as a multimodal practice, always related to a story, enabled by the specific qualities of its contextualizing medium. As practice-led research, the thesis explores this proposition in practice and theory within printed and online forms of editorial illustration and in relation to online media technologies and material properties. Central is the development of a potential method of online editorial illustration that I call data driven illustration, a formation employing the material and semiotic expressive potential of live data and code. The research draws primarily from the ideas of media materiality (Hayles, Kittler, Manovich), but in doing so is supplemented with other relevant theories found in semiotics (Barthes, Hayles, Kress and van Leeuwen) and audience reception (Hall). This interdisciplinary approach is applied to the field of illustration through a historical study of wood-engraved news illustration in the Illustrated London News; through my own practice as an illustrator, in this case, work undertaken for the NRC newspaper; and explorations of various examples of online illustration. This thesis offers a first step in constructing a framework for editorial illustration, to move beyond the print paradigm and provide a language through which to explore illustration as an emergent practice.