It has recently been suggested that in Machiavelli's appreciation of what is grave and what is ridiculous “can be recognized … the spirit of modernity in its early phases, when it was fresh, bright, and eager.” This admittedly problematical assertion draws attention to Machiavelli's transformation of the premodern perception of gravity, wherein gravity and piety are closely associated. In this article, we consider how Machiavelli changes men's approach to gravity and piety by examining in particular his treatment of Dante, a representative of the premodern point of view. We find that Machiavelli discards the old view of gravity and piety because of its utility to the church and because Christian gravity is a safeguard against too readlly taking oaths, one of the things critical for Machiavelli's enterprise.