This article studies the idea of imitation from classical philosophy to the contemporary digital age. It begins with Plato’s theory of mimesis in The Republic, where poetry is viewed with suspicion because it imitates appearances and may mislead reason and morality. It then examines Aristotle’s defence of poetry in the Poetics, where imitation is treated as a natural human activity that produces knowledge, emotional clarification, and universal truth. The discussion next moves to modern theories of representation and mediation through Walter Benjamin, Neil Postman, and Sherry Turkle, who explain how technology alters perception, public discourse, and human relationships. The article further considers Jean Baudrillard’s concept of simulation and hyperreality, where images no longer copy reality but replace it. In this context, artificial intelligence and social media create virtual environments that operate without direct reference to lived experience. The study argues that such conditions revive Plato’s concerns about truth and ethical responsibility. At the same time, it shows that Aristotle’s view of imitation as creative is relevant, especially in understanding literature as a conscious and reflective form of representation. By comparing poetry with digital simulation, the article concludes that literary art continues to provide critical awareness and moral imagination in an age dominated by virtual realities. The debate on imitation thus remains central to both classical aesthetics and contemporary culture