The objective of this essay is to compare the works of novelist Philip Roth and film-maker Woody Allen in what regards their treatment of the highly complex theme of the interrelations between fiction and reality. A comparative analysis of selected Roth’s novels and Allen’s films evinces their recurrent preoccupation with the creation of art and its implications, be it through the choice of writers or artists as main characters, be it through plots that mix real facts with invented ones and imaginary characters with real ones, be it through the use of autobiographical elements in a fictional discourse—all metafictional devices that call attention to the artist’s own process of creation.