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The classic treatise on how to tyrannize one's subjects.
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The Prince is a book that was controversial before it had even been sent to the printer. Written in vernacular Italian instead of Latin, dedicated to a member of one of the most powerful Italian families of the day, and only printed after Machiavelli's death, this treatise on how to tyrannize effectively was considered shocking even by his contemporaries. The discussion of its morality that continues to this day gives us the modern-day word Machiavellian.
I: How Many Kinds of Principalities There Are, and by What Means They Are Acquired
II: Concerning Hereditary Principalities
III: Concerning Mixed Principalities
IV: Why the Kingdom of Darius, Conquered by Alexander, Did Not Rebel Against the Successors of Alexander at His Death
V: Concerning the Way to Govern Cities or Principalities Which Lived Under Their Own Laws Before They Were Annexed
VI: Concerning New Principalities Which Are Acquired by One's Own Arms and Ability
VII: Concerning New Principalities Which Are Acquired Either by the Arms of Others or by Good Fortune
VIII: Concerning Those Who Have Obtained a Principality by Wickedness
IX: Concerning a Civil Principality
X: Concerning the Way in Which the Strength of All Principalities Ought to Be Measured
XI: Concerning Ecclesiastical Principalities
XII: How Many Kinds of Soldiery There Are, and Concerning Mercenaries
XIII: Concerning Auxiliaries, Mixed Soldiery, and One's Own
XIV: That Which Concerns a Prince on the Subject of the Art of War
XV: Concerning Things for Which Men, and Especially Princes, Are Praised or Blamed
XVI: Concerning Liberality and Meanness
XVII: Concerning Cruelty and Clemency, and Whether It Is Better to Be Loved Than Feared
XVIII: Concerning the Way in Which Princes Should Keep Faith
XIX: That One Should Avoid Being Despised and Hated
XX: Are Fortresses, and Many Other Things to Which Princes Often Resort, Advantageous or Hurtful?
XXI: How a Prince Should Conduct Himself So as to Gain Renown
XXII: Concerning the Secretaries of Princes
XXIII: How Flatterers Should Be Avoided
XXIV: Why the Princes of Italy Have Lost Their States
XXV: What Fortune Can Effect in Human Affairs and How to Withstand Her
XXVI: An Exhortation to Liberate Italy from the Barbarians