As a space of extremes, the skyscraper has been continually constructed as an urban frontier in American cultural productions. Like its counterpart of the American wilderness, this vertical frontier serves as a privileged site for both subversion and excessive control. Beyond common metaphoric readings, this study models the skyscraper not only as a Foucauldian heterotopia, but also as a complex network of human and nonhuman actors while retracing its development from its initial assemblage during the 19^th century to its steady evolution into a smart structure from the mid-20^th century onward. It takes a close look at US-American literary and filmic fictions and the ways in which they sought to make sense of this extraordinary structure throughout the 20^th and early 21^st centuries. More traditional poststructuralist spatial theories are connected with concepts and methods of Actor-Network Theory in a compelling account of the skyscraper’s evolution as reflected in fictional media from early 20^th-century short stories via a range of action, disaster and horror films to selected city novels of the 1990s and 2000s.