Historically, Academia has been the main framer of legal identity, shaping the limits of the Law and the boundaries of legal thinking. In this study, I am concerned with how legal education will sculpt twenty-first century jurists’ forma mentis regarding the area of the Philosophy of Human Rights. This field has been mainly subjected to the vices and myths that are commonly held to underpin the hegemonic approaches to International and Natural Laws, thereby reaffirming their original Eurocentric, colonial, capitalist, and religious biases. At the same time, the ground for a counter-hegemonic Philosophy of Human Rights has been already laid out by some critical legal scholars, through the examination of legal mythologies and paradoxes, and via the radical innovations due to NAIL, TWAIL and Decolonial Theory. However, the field of Philosophy of Human Rights still lacks an aggregated analysis of its key-Events and generated Imaginary, in order to provide a proper ‘pedagogical turn’. This is where my research and educational proposal fit. Under a ‘history from below’ perspective, drawing on those critical legal streams and adopting a Foucaultian and Blochean mixed-approach, I scrutinize the foundational Events of Philosophy of Human Rights, emphasizing their ‘Darker Side’ and the colonialism/slavery axis. From the Colonial Encounter to the Universal Declaration of Human Rights, I highlight the repressive and the emancipatory dimensions of such key-moments, and how they shaped the legal imagination. My aim is to provide tools and a guideline for the deconstruction of some of the main modern mythologies and narratives that restrain such imagination, thereby enlarging it towards counter-hegemonic legal horizons and possibilities.