This chapter examines the role of paradox in the films and film theory of Ken Jacobs, Hollis Frampton, and Michael Snow. Paradoxes such as Zeno’s paradox, Gödel’s incompleteness theorem, and Benoît Mandelbrot’s fractal theory of geometry, which inform the work of these filmmakers, propose and repeat the unresolvable gap between subject and world that informs skepticism. This chapter argues that the skeptical encounters these films invite, which entice the spectator to work toward solving a riddle or problem of incompleteness, also provide a model for overcoming skepticism by prompting re-encounters with the images on screen and the world to which they refer. These re-encounters occur in the same way that Stanley Cavell imagined the images of mainstream cinema could overcome problems of philosophical skepticism by drawing the subject closer to the world. The author argues, however, that these avant-garde meditations on mises en abyme are possibly more effective than Hollywood filmmaking for overcoming skepticism because of their more immediate emphasis on cinema’s very ability to engage and stage re-encounters between the subject and the limits of the world, rather than their reference to the world through images.