This chapter offers a comparative perspective on the relationship between the social and the aesthetic by contrasting the development of an Afro-modernist aesthetic of politics and music in American jazz improvisation of the 1950s and 1960s and the aesthetics of sensibilisation in the contemporary musical aesthetics of Mali. Both musical traditions are highly improvisational and virtuosic but articulate the connections among social, ethical, religious, and musical in different ways. In Mali, the idea of sensibilsation as an important activity for popular artists involves educating broad audiences about major issues of social, political, ethical, and medical concern through lyrics and performance styles that raise awareness through a combination of contemporary information and traditional modalities of expression. Race was the primary social variable examined and articulated in the social aesthetics of jazz in the 1950s and 1960s; gender, health, and economic aspirations provide the central points of social aesthetics in contemporary Mali. A comparative perspective on the aesthetics of improvisation provides insight into how processes of improvisation can carry a wide variety of relationships to the social.