Dante Alighieri's Inferno and Niccolò Machiavelli's The Prince are both works born from the religious culture of Italy; but that aside, the two, in terms of message, appear to be as different as night and day, as each is distinct from the other in how it presents the nature of morality to its readers. For Dante, morality is carved in stone, something absolute and directly related to the maintenance of public order; Machiavelli, on the other hand, presents morality as a flexible nature, a mere institution that is ultimately in the eye of the beholder, and which has no real weight in the affairs of the real world, except when it can be used to own advantage. But while on the surface these two moral guidelines seem so different from each other, in essence they are similar for a reason: both, despite coming from different time periods, highlight how morality is problematic. So, in short, despite the differences in how the two works deal with the question of morality, they both raise questions about the best, or wisest, way to live one's life. in terms of the moral lessons they provide to their readers, it is necessary to have a solid understanding of the cultural events surrounding the two works. For starters, although the areas from which Dante and Machiavelli wrote are relatively close, the times in which the two writers lived differ by about two hundred years. A lot can change in two centuries, and it certainly happened in this case. For example, the Catholic Church had an active role in political affairs at the time Dante wrote his Inferno, while the secular powers of the Eu...... middle of paper ......lem with morality today as, I am sure, it was both in the times of Alighieri and Machiavelli. So, although they may seem very different, the two philosophies – one of a religiously devout man and the other of a man who cared nothing about religion – are essentially haunted by the same question, despite being separated by two centuries and countless changes in the way people view religion and morality: Is it possible for a person to seek happiness and security on earth and remain morally upright? In view of all this, then, I suppose that each of us has been given an ultimatum from above, namely: either we sacrifice worldly happiness and security for the sake of righteousness, as Alighieri suggests, or we follow the plan of action of Machiavelli and we sacrifice righteousness for justice. for the sake of happiness and security on earth. For now, however, there is no middle ground.