Focusing on the work of Harriet Monroe and Selma Walden, two Chicago writers who never fully identified with their literary milieus, this essay complicates the perceived divide between the Victorian and the modern, the old and the new. In his 1900 American Anthology, Monroe’s friend and mentor Edmund Clarence Stedman dubbed the turn of the century an “interval of twilight” for American poetry. Subsequent critics have perhaps read this narrative of decline too literally and regarded the supposed interregnum as a sign of progress toward modernism. This essay takes a different approach: understanding narratives of poetry’s twilight as strategic fictions that idealize, preserve, and recirculate the poetry of an earlier period. It views Monroe and Walden as productive symptoms of a critical tendency to incorporate narratives about Victorian poetry into narratives about modernism. Considered together, Monroe and Walden demonstrate how the Victorian had complex afterlives in twentieth-century America. Their works show how the tension between the Victorian and the modern reemerged during the twentieth century, playing out on different levels of culture.