With its publishing success and widespread recognition by critics, the novel The Overstory by Richard Powers highlighted and confirmed the importance of literature in awakening ecological consciousness. For this reason, despite its recent publication, there is a constant increase in articles and publications that approach it in various interpretive ways. In this essay, the researcher focuses on clarifying and examining the philosophical implications of the novel. The study highlights that literature, and in this case, The Overstory, can be a privileged field of co-alignment and coexistence of different eco-philosophies, which, although they share the same goal, differ in terms of how to achieve it. The study will focus on two theories, Timothy Morton’s Dark Ecology and Jane Bennett’s Vital Materiality, to show how both are reflected in the novel. By employing two metaphors, “the forest” and “the tree,” he will connect them to Jane Bennett’s Thing Power and Timothy Morton’s Hyperobjects, to show how Richard Powers hesitates to choose between an ethical-philosophical stance that favors interconnectedness and symbiosis, and another one that strives to shield Nature’s alterity and singularity. The result is a coexistence of two disparate eco-theories that lead to double-faced ethics. Richard Powers, in fact, insists that one must simultaneously be seduced by Nature’s strangeness and feel intimacy with it to cope with the ecological crisis.