This chapter explores the philosophical notion of The Virtual in response to the writings of Gilles Deleuze and unfolds this thinking through its interdisciplinary and transformative affects upon contemporary fine art. The Virtual will be discussed in relation to forms of contemporary painting, yet, provides a model for thinking through interdisciplinarity within, and from, other media. The research investigates the perceived resistance of painting to explore external possibilities and introduces methodological strategies, which encounter externality as a means for establishing radical change. In this way the Virtual acts as an instigator for change, which effectively destabilises the pre-formity attached to medium specific practices. It is for this reason that the Virtual forces external relationships and connections to come to the fore in order to radically alter and transform the physical and conceptual constructs of different disciplines. Alongside the discussion of the Virtual and its direct affects upon artistic practices the chapter discusses literary models including hybridity and metamorphosis as potential key elements affecting transformative change.