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The Renaissance dialogue has often been discussed in terms of its hybridity. Carlo Sigonio, Sperone Speroni and Torquato Tasso identified prose, poetry, philosophy, rhetoric and dialectic when writing about the genre. This notion of the dialogue’s hybridity continues also among contemporary critics who have also cited (among others) treatise, theatre and narrative. This liminality has proved problematic in some cases for the writers of Renaissance dialogue, and this paper will briefly examine the genre’s history and highlight the contribution to this history from an unlikely source, namely Niccolò Machiavelli. To engage and dialogue with his reader was one of Machiavelli’s greatest talents, yet today he is not immediately thought of when we discuss the masters of the dialogic genre. Through a discussion of his dialogic works, this paper will identify the dialogic elements that helped make masterpieces of his more famous works Il principe and La Mandragola.