This chapter examines how American literature has engaged with business corporations in general, and the legal fiction of corporate personhood in particular. There are few major novels about business corporations, because literary fiction has tended to concentrate on the moral dilemmas and social entanglements of individuals, rather than the more impersonal realm of economic activity. Yet the changing legal nature and increasing importance of corporations has forced some writers to rethink what it means to be human, creatively rethinking the relationship between individual and collective agency. The chapter considers three phases in the literary representation of corporations: as monster, as system, and as story. It uses as examples James Fenimore Cooper’s The Bravo (1831), Frank Norris’s The Octopus (1901), Sloan Wilson’s The Man in the Gray Flannel Suit (1955), Joseph Heller’s Catch-22 (1961), Thomas Pynchon’s Gravity’s Rainbow (1973), Richard Powers’s Gain (1998), and Joshua Ferris’s Then We Came to the End (2007).