Focusing on Bosnia, Croatia, and Serbia, this article examines film and music that emerged in the region since the end of the Yugoslav Wars of Succession. We analyze how the uncertainties of the postwar era facilitated a dynamic field of cultural contestation in which the music and film industries simultaneously challenge and affirm normative masculine sociocultural roles. Although traditional norms have not lost their primacy in public life, we emphasize the fact that attitudes toward masculinity have, in general, become increasingly ambiguous and multivalent. While local sociological studies accurately observe that violence and intolerance constitute central traits for the majority of men in the West Balkans, our research reflects on how popular culture complicates the idea that postwar West Balkan masculinities have remained uniform, static, and defined exclusively by aggression. We thus focus on the most popular musical and cinematic productions that embody the tension inherent in the contemporary representations of West Balkan masculinity. From our examples, it becomes clear that generalized instability attending new market economies and postwar political turmoil have indeed created a context within which national gender norms have entered a state of flux.