Drawing on Deleuze’s account of the “virtual” as no less “real” than the “actual”, this article considers Peter Watkins’s and Mark Rappaport’s cinematic oeuvres in view of a more general discussion as to whether and how cinema captures or expresses reality. Despite their differences, both filmmakers share an intense interest in the entwinement of fiction and documentary, whose peculiarity the concept of the “virtual” may help clarify. In particular, they both made films about non-fictional people and events—artists, battles, revolutions—which cannot be labelled as documentaries due to their formal characteristics. In the end, these works suggest that the strength of cinema consists in breaking the vicious circle of the actual and the possible. Rather than mixing reality and fiction, cinema would express the impossibilities of the past and the contingencies of the future, whose virtuality insists through the interstices of the world as its everlasting shadow.