Plato would agree with Jean Baudrillard about the imaginary concept of Disneyland to describe today’s world ideas. If Plato lived in our modern era, he would have said much about it, especially as it is conditioned by the many postmodern phenomena and political conflicts. In this conference that underlines the relevance of Greek philosophy in the modern era, I intend to consider Plato’s Allegory of the Cave presented in his The Republic in order to analyze its relevance in the now-so called “age of information” saturated with excessive media, high-technology, cyberspace, and late-capitalism. In this discussion, I elaborate on the idea of the “modern cave” that is reshaped by postmodern ideologies that create a more unreal world. Theoretically, I not only use Plato’s philosophy in order to evaluate contemporary world reality, but I also use postmodern Western thought like that of Baudrillard, Jacques Lacan, and Slavoj Žižek so as to critically examine postmodern culture that is dominated by late-capitalist and hegemonic ideologies. Examples from literature, culture, and politics will be used to enrich the discussion.