This paper explores the connections between math, as seen in the interplay of chaos and fractals, and literature, as seen in the form and structure of Dante's Divine Comedy and Stoppard's play Arcadia. Dante seems to intuitively grasp the order in the chaos that Benoit Mandelbrot and those that followed after him would formalize within fractal theory and dynamical systems theory centuries later. Stoppard is a separate case, showing that order and chaos are human themes, and also by bringing mathematics directly into his play. Stoppard's intentional and un-intentional connections serve as a bridge between the mathematics of fractals and the literature of Dante, and show that these two disparate disciplines connect on a fundamental and human level.