This article argues that Stanley Cavell's notion of moral perfectionism must be understood, within the American cultural context, as deeply intertwined with myths of heroic American masculinity. It traces connections between Cavell's descriptions of moral perfectionism, the transcendentalist authors on whom he relies, and writings about the myth of the American frontier hero. When understood as a tradition of masculinity, it becomes possible to trace moral perfectionism across much wider areas of American cinematic culture than Cavell's reading suggests; Good Will (...) Hunting is used as an example which further illuminates the relationship between moral perfectionism and American masculinities. Psychoanalysis, a major feature of Good Will Hunting as well as an important aspect of Cavellian moral perfectionism, must also be revisited in terms of the differences in its popular mythologisation for men versus for women. (shrink)