The article examines a dimension of ethics that Stanley Cavell names moral perfectionism, gathering under this label a host of different authors and philosophical lines, with Ludwig Wittgenstein holding the center stage. This dimension of ethics focuses on the mobility and transformation of the self, and in this light it is interesting to compare this approach with virtue ethics, given their shared emphasis on the self, its peculiar status, and the prospect of education. The idea of self-transformation informs Wittgenstein’s and Cavell’s philosophies in a number of ways. In particular, we can say that in Cavell’s perspective one’s comfort and happiness are gained piecemeal and repeatedly—as comedies vividly teach us—through a process which transforms the shameful circumstances of life into occasions for interest and pleasure. What constitutes a source of insecurity and disgrace is constantly and repeatedly transformed into a source of pleasure, exchange, and company. The confrontation with virtue ethics allows us to specify the peculiarity of perfectionist self-transformation. Some versions of virtue ethics, such as the one elaborated by John McDowell, share with moral perfectionism a firm antitheoretical approach which traces ethics back to the moral life—exemplified on the one hand by one’s individual sensibility and personal orientation and on the other by life with other people—that shapes one’s sensibility and orientation in an overall culture. The peculiarity and specificity of the tradition of moral perfectionism can be best appreciated against the background of a shared approach to the moral life.