This article explores notions of masculinity and belonging in Tarell Alvin McCraney’s The Brothers Size. McCraney creates complex characters that problematize collectivist notions of African American identity. Through a raw theater style, syncretic blendings and great linguistic musicality, The Brothers Size interrogates African American masculinity by contrasting the intimate lives of the characters with ideas, patterns and expectations that reduce Black, male existence to racial discourses and conflicts. His dramaturgy rethinks the Black, male character by furthering individuality, interaction and difference.