In this article I explore the nature of the relationship between art and terror/ism and ask why identifications between the two are so routinely and often insistently made. In so doing, my aim is twofold. Firstly, I explore the possibility of there being a deep-seated structural link that exists between art, terror/ism and creativity. In other words, I ask if terror is a necessary corollary of the ‘creative event’. Secondly, I explore explicit examples in which artists have sought to create or to emphasise this relationship, from the perspective of Contemporary Art practices. In the spirit of experiment rather than of judgment then, this article sets up a series of trials in which art and terror/ism are philosophically, aesthetically and politically blended. It asks where else should such tests be conducted, if not in relation to the artwork and in particular, in relation to those artworks which toy with terror/ism and those artists who claim on some level, to be ‘terrorists’? How is the ‘artist-as-terrorist’ to be interpreted and understood alongside existing definitions of both terrorism and of Art? And finally, what role does imagination play in the construction of experience?