Niccolo Machiavelli’s The Prince remains an influential book more than five centuries after he wrote his timeless classic. However, the political philosophy expressed by Machiavelli in his tome is often misunderstood. Although he thought humans to be rational, self-interested creatures, and even though he proposed an approach to politics in which the ends justify the means, Machiavelli was not, as some have argued, simply a teacher of evil. The Prince’s many ancient and medieval examples, while relevant to sixteenth century readers, are lost on most of today’s students of Machiavelli. Examples from modern films and television programs, which are more familiar and understandable to contemporary readers, provide a better way to accurately teach Machiavelli’s lessons. Indeed, modern media, such as Breaking Bad, The Godfather, The Walking Dead, Charlie Wilson’s War, House of Cards, Argo, and The Departed, are replete with illustrations that teach Machiavelli’s critical principles, including the need to caress or annihilate, learning how not to be good, why it is better to be feared than loved, and how to act as both the lion and the fox. Modern media are used in this book to exemplify the tactics Machiavelli advocated and to comprehensively demonstrate that Machiavelli intended for government actors and those exercising power in other contexts to fight for a greater good and strive to achieve glory.