Modernity loves noble aspirations; the image of a hero following the path of adventure in order to save the universe and become happy forms the center of many works of art. Often, the image of such a hero is reinforced by the idea of magnanimity, that is, the idea of a moral character that allows its owner to overcome emerging difficulties and cope with outstanding circumstances. However, for a long time, ideas about generosity did not have the degree of unambiguity that we put into this word now. For example, in the Middle Ages, generosity was strongly associated with the sin of pride, and therefore commentators on Aristotle (for example, Albertus Magnus) tried to find a clear substantive difference between magnanimitas and superbia. For this reason, critical concepts of Aristotle and Hegel are interesting, because they show that the great soul (or beautiful soul) does not have noble connotations, for they are ironic (or ordinary). Both Aristotle and Hegel greatly influenced subsequent ideas about generosity; by showing its dual nature, they showed the “other side” of this virtue. This article provides a consistent analysis of Aristotle’s ideas about generosity, set out in the Nicomachean Ethics, and Hegel’s Gestalt, described in the Phenomenology of Spirit. The final section presents a comparison of the two concepts, revealing which critical foundations are significant for both Hegel and Aristotle, and also describes possible lines of further research