Cynicism – understood both in its ancient sense as a Hellenistic philosophical school, and in its modern sense as an enlightened false consciousness – is the subject of the present thesis. Starting with the question How to write a history of cynicism?, we intend to assess the conditions of possibility and, at the same time, propose such a history. To deal with this endeavour, we resorted to the notion of cynical dialectic. In our opening chapter, we present four key moments in the history of Cynicism – personified by Diogenes of Sinope, Lucian of Samosata, Jean-Jacques Rousseau/Denis Diderot and Friedrich Nietzsche. After that, we examine the recent historiography on the subject, focusing on the works of Heinrich Niehues-Probsting, Peter Sloterdijk and Michel Foucault. Finally, in the last chapter, we reflect on what the cynical dialectic is and how its dynamics works. Our objective, after going through the entire text, is to make clear how the cynical discourse operates in a dialectical way, inasmuch as it always slips away from its own definition.