As they are made from diffracted light one of the most important pictorial agencies of the holographic image is darkness. Although several holographic artists have employed this unique darkness, which can be constructed in optical holograms by spatio/temporal events during the exposure, the meaning of this darkness has been difficult to interpret by the audience. This holographic research visualises ideas about darkness proposed by Michael Baxandall in the book Shadows and Enlightenment. Shadowy Figures by Paula Dawson is a digital reflection hologram with a scale of 120x120cm. The project emulates, in 3D, aspects of darkness from three case studies: Giotto’s fresco Joachim and the Shepherds, Masaccio’s fresco Baptism of the Neophytes, and Leonardo da Vinci’s Drapery Study. The hologram demonstrates the relative suitability of the conventions of using darkness established by Giotto, Masaccio and Leonardo da Vinci thereby providing a new means of reading the virtual space of the holographic image. The work is the primary visual output of research findings of ARC Discovery Project, Shadowy Figures. The significance of Shadowy Figures is demonstrated by its display Light from Shadow: The Legacy of Chiaroscuro in Spatial Imaging at Ivan Dougherty Gallery, Sydney, which was well reviewed and covered extensively by local media. An article on the exhibition by Coyle, R. 2004. Review of Light from Shadow, was published in Convergence, The International Journal of Research into New Media Technologies, 10/3, pp.110-114.