Play is a gendered activity among young children, especially boys. Boys often tend to be more actively engaged in the (re)production of gendered play. However, most research studies and conceptual papers have misread, ignored, devalued, or scrutinized the gendered ways Black boys engage in play. This idea is particularly true for Black boys who may not play within the monolithic gendered expectations of childhood play. Drawing from [Connell, R. W. (1995). "Masculinities." Berkeley: University of California Press] notion of multiple masculinities, I propose what I call the performance of 'multiple masculinities of Black boys' childhood play' to embrace the ways some Black boys engage in play activities, which may not fit within the performance of hegemonic and Black masculine norms and expectations. In so doing, I call for educators to broaden how we view Black boys, and our definition of Black masculinity so that embracing what might be traditionally called 'less masculine' and/or stereotypically feminine could be valued male traits. Recommendations are provided for early childhood educators to support the confluence of ways Black boys engage in play experiences.