The imagery of spider webs has always been characterized by a fundamental ambivalence. Disgust and admiration, transience and eternal cycle, demonization and attribution to divine genius are combined in this image much like nature and technology or woman and man. After a description of the cultural-historical roots of this dialectic relationship the paper addresses the aesthetic of the cobweb and analyses on that basis the narrative formations of the metaphor. The myth of Arachne in Ovid's Metamorphoses serves here as a reference for a reading of three modern texts: Hanns Heinz Ewer’ Die Spinne, Ken Kesey's One flew over the cuckoo's nest and Manuel Puig's El beso de la mujer araña. I argue that spider webs illustrate asymmetrical and gendered power structures, in which negatively connotated spiders represent femininity. Furthermore, in literary texts spider webs seems to symbolize the eternal provisional arrangement that characterizes the life of modern figures. That may be considered as an updating of the tension between immanence and transcendence which existed since Arachne.