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Machiavelli: The Prince (Cambridge Texts in the History of Political Thought)Machiavelli: The Prince (Cambridge Texts in the History of Political Thought) by Niccolo Machiavelli
Buy new: $8.57 / Used from: $0.14
Probably the best translation of Machiavelli's classic in English. It is actually a much less nefarious than its supposed fans would lead you to believe.
Discourses on Livy (Oxford World's Classics)Discourses on Livy (Oxford World's Classics) by Niccolo Machiavelli
Buy used from: $7.32
Until recently this was Machiavelli's most renowned work, and exerted a huge influence on the Founder of the U.S. John Adams especially was an admirer of its republicanism.
Florentine HistoriesFlorentine Histories by Niccolo Machiavelli
Buy used from: $9.25
A history of why previous Florentine governments had failed and why they succeded when they did. A defense of republicanism lies throughout the work.
Machiavelli: The Chief Works and Others (3 Vol. Set)Machiavelli: The Chief Works and Others (3 Vol. Set) by Nicollò di Bernado deiMachiavelli
Buy used from: $49.95
Excellent three-volume edition containing all of Machiavelli's major works in superb translation.
The Letters of Machiavelli : A SelectionThe Letters of Machiavelli : A Selection by Niccolo Machiavelli
Buy new: $20.00 / Used from: $6.45
An excellent collection and translation of key letters by Allan Gilbert, a prominent translator of his work.
The History of ItalyThe History of Italy by Francesco Guicciardini
Buy new: $21.12 / Used from: $3.89
An important work by Machiavelli's fellow Florentine.
Guicciardini: Dialogue on the Government of Florence (Cambridge Texts in the History of Political Thought)Guicciardini: Dialogue on the Government of Florence (Cambridge Texts in the History of Political Thought) by Francesco Guicciardini
Buy used from: $29.98
Guicciardini is unjustly neglected by contemporary students of the history of political philosophy. He and Machiavelli should be studied in tandem.
Machiavelli and Guicciardini : Politics and History in Sixteenth-Century FlorenceMachiavelli and Guicciardini : Politics and History in Sixteenth-Century Florence by Gilbert Felix
Buy new: $23.95 / Used from: $14.39
An important study by Felix Gilbert--not to be confused with Allan--on the two great Florentine philosophers.
Machiavelli: A Very Short Introduction (Very Short Introductions)Machiavelli: A Very Short Introduction (Very Short Introductions) by Quentin Skinner
Buy new: $9.32 / Used from: $2.50
A spectacular short study of Machiavelli. A great first book on Machiavelli by one of the foremost historians of political philosophy of our era.
Machiavellian Moment Florentine Political ThoughtMachiavellian Moment Florentine Political Thought by J. G. A Pocock
Buy used from: $45.65
A classic. The United States is a republic, yet very few Americans understand the historical context for the formation of the nation as a republic. This book helps provides that context.
Machiavelli and Republicanism (Ideas in Context)Machiavelli and Republicanism (Ideas in Context)
Buy new: $34.99 / Used from: $27.24
A very strong collection of articles by many of the world's leading authorities on the subject. Highly recommended.
Life of Niccolò MachiavelliLife of Niccolò Machiavelli by Roberto Ridolfi
Buy used from: $146.12
The standard biography in English. You might have to search for this in a good research library.
Machiavelli in HellMachiavelli in Hell by Sebastian De Grazia
Buy new: $14.78 / Used from: $1.31
A very curious book, though a fascinating one.
Niccolo's Smile: A Biography of MachiavelliNiccolo's Smile: A Biography of Machiavelli by Dr. Maurizio Viroli
Buy new: $11.25 / Used from: $3.74
Another recent biography. Less interesting than MACHIAVELLI IN HELL, though more trustworthy overall.
Machiavelli (Founders of Modern Political and Social Thought)Machiavelli (Founders of Modern Political and Social Thought) by Maurizio Viroli
Buy new: $55.00 / Used from: $23.82
A strong recent interpretation of Machiavelli's thought.
Machiavelli and Empire (Ideas in Context)Machiavelli and Empire (Ideas in Context) by Mikael Hörnqvist
Buy new: $83.46 / Used from: $95.11
I have not read this volume, but any volume in the Ideas in Context series deserves a look.
The Machiavellian CosmosThe Machiavellian Cosmos by Professor Anthony J. Parel
Buy new: $48.00 / Used from: $17.95
An attempt to situate Machiavelli in his intellectual worldview.
Fortune Is a Woman : Gender and Politics in the Thought of Nicollo Machiavelli : With a New AfterwordFortune Is a Woman : Gender and Politics in the Thought of Nicollo Machiavelli : With a New Afterword by Hanna Fenichel Pitkin
Buy new: $21.00 / Used from: $5.24
An interesting gender studies approach to Machiavelli.
The Foundations of Modern Political Thought, Vol. 1: The RenaissanceThe Foundations of Modern Political Thought, Vol. 1: The Renaissance by Quentin Skinner
Buy new: $28.04 / Used from: $14.11
A masterpiece by a one of the great scholars of his age. Crucial on the overall context of Machiavelli's thought.
The Foundations of Modern Political Thought, Vol. 2: The Age of ReformationThe Foundations of Modern Political Thought, Vol. 2: The Age of Reformation by Quentin Skinner
Buy new: $23.32 / Used from: $16.10
Continues volume two into the Reformation, a period too often neglected by historians of philosophy.
The Cambridge History of Medieval Political Thought c.350-c.1450 (The Cambridge History of Political Thought)The Cambridge History of Medieval Political Thought c.350-c.1450 (The Cambridge History of Political Thought)
Buy new: $54.02 / Used from: $47.65
An important collection of essays that provide the historical background for Machiavelli's thought.
The Cambridge History of Political Thought 1450-1700The Cambridge History of Political Thought 1450-1700
Buy new: $40.16 / Used from: $36.87
Continues the previous volume into Machiavelli's age and beyond.
Renaissance Florence, Updated editionRenaissance Florence, Updated edition by Gene A. Brucker
Buy new: $12.38 / Used from: $1.25
Provides the overall historical context of Machiavelli's city.
Renaissance Philosophy (History of Western Philosophy)Renaissance Philosophy (History of Western Philosophy) by Brian P. Copenhaver
Buy new: $45.00 / Used from: $19.80
A fine survey of Renaissance philosophy. Ably situates Machiavelli in the larger intellectual landscape.
Thoughts on MachiavelliThoughts on Machiavelli by Leo Strauss
Buy new: $13.90 / Used from: $10.75
Except for Neocons and Straussians, Leo Strauss is almost universally regarded as a nut. I don't recommend this, but one should know it exists.