Strange as it might seem to put Al-Farabi and Machiavelli alongside each other, the unity of the essence of philosophy provides a basis for a comparative outlook. The present article is an endeavour to introduce a new comparative reading of the political philosophy of Abu Nasr Al-Farabi (870 –950) and Niccol Machiavelli (1469 – 1527) as two influential figures in the political philosophy of Islam and the modern political philosophy of the west. For this purpose, some of Al-Farabi’s works which have not attracted much attention and Machiavelli’s major political treatises are examined with a realistic empirical approach to present a realistic picture of Al-Farabi’s political philosophy and a philosophical picture of Machiavelli’s political thought. The reading through initiation of a dialogue between the two great thinkers is intended to open a window through which we can appreciate the efficacy of our dignitaries and in this way take a step into the real world. To achieve this aim, we first present the similarities and differences identified in the political thought of the two philosophers. The similarities are consideration of facts, the importance of empirical perception, presentation of the foundations of politics and the relationship between politics andanthropology.The differences are the different religious backgrounds, the differential emphasis on objectivity and subjectivity, the relationship between politics and existence and the allegory of the physician. The conclusion is that rationality underlying Al-Farabi’s political philosophy has a lot of potentiality for the development and efficacy of human beings, while Machiavelli’s radical subjectivism and pessimism has negative consequences for the world. While Al-Farabi’s rationalism is empirically-based and is consistent with the foundations of the modern world and man’s awareness and freedom and as a result useful for us in this world, Machiavelli’s egocentric and fortuitous thought makes fear and horror as a natural state of human minds.