This essay explores culturally derived and institutionally sanctioned gender portrayals in classical ballet by focusing on the historical evolution of pointe work. Despite some recent experiments, ballet men tend to dance on pointe only for comic effect, as in Les Ballets Trockadero. The contempormy exception of a scene from choreographer Edouard Lock's Amelia is examined and, for comparison, hermeneutical dance analysis is also applied to the practice of Georgian folk dance men, who dance on their toes in a form where women do not. It is suggested that both ballet women on pointe and Georgian men on their toes embody the qualities of athletic strength (often coded male) and softly graceful elegance (often coded female), and that examining and challenging these culturally rooted practices reveals underlying, persistent stereotypes that inhibit the evolution of both ballet and theatricalized folk dance.