In Vilém Flusser’s universe, the term chaos expresses – simultaneously and paradoxically – the states of the disorder of matter (negative) and the creative possibilities of unstable and unpredictable systems (positive). When asked about the centrality of the concept of chaos in his thinking, Flusser employed the contemporary view of science in order to defend a probability-conform perspective of coincidences. Coincidences must be seen as “statistical necessities”; as a result, “order has to be understood as a statistical exception of chaos” (Zwiegespräche, 1996, p. 78; translated from the German). Viewed from this perspective, the traditional idea of truth loses its meaning. Truth as a unique reference disappears in favor of the more or less probable. Everything is thus expressed on different levels of probabilities. What really interests us as human beings is improbability as an expression of the new, of creation, and of negentropic processes. Chaos is thus revealed to be a productive energy, as a dimension of the unexpected, of innovation, the increase of information that combats entropy. In this new scenario – which also demands a new ontology – the computer would, according to Flusser, be the ideal apparatus not only to compute, but also to produce images of new possible worlds. Hence the problem seems to exist in a complex equilibrium between order and disorder, in which the one should not eliminate the other. Since “without a dwelling, without protection of the ordinary and familiar, everything that arrives is noise, nothing is information” (Bodenlos, 1992, p. 260; translated from the German). Chaos is therefore both a horrifying expression of the unformed (without information) and the necessary opening up to the undetermined, to the improbable. Art is certainly an essential and privileged form of dealing with the dialectic of chaos and order.