In this essay, I argue that it’s theoretically and historically misleading to talk about a break between modernism and postmodernism, and more specifically, that thinkers such as Foucault and Derrida, two figures frequently associated with the postmodern turn, are situated within certain rational, enlightenment and modernist traditions. As part of this claim, I explore how features such as essentialism, binarism, determinism, positivism, and productivism are not characteristics that can be applied to all of enlightenment thought and modernism, and that such a description of the enlightenment and modernism would themselves be essentialist and caught up in binaries. To illustrate these arguments, I re-read figures such as Berkeley, Schopenhauer, Nietzsche, and a range of Modern artists (especially their conceptualizations about essences, representations, and processes), tracing patterns such as plurality, particularity, and absurdity/incoherence throughout their thought. After historical and theoretical overview, I connect the experiential and philosophical patterns existing before our so-called “postmodern turn” to an examination of Foucault’s rational methodology and critical ontology, as well as his theorization of enlightenment thought, power/knowledge, ethics, and resistance (especially in, but not limited to, his later works). Through all of this, I ultimately show that 1) Rather than a break, postmodernism signifies an extrapolation of certain pre-existing enlightenment and modernist trends, and 2) Michel Foucault can be claimed as both an enlightenment thinker and a modernist. Such a set of arguments, if deduced as correct by readers, might restructure traditional understandings of postmodernism and the legacy of enlightenment thought.