Growing up, I often came across classic cartoons and older theatre productions that, at first glance, seemed simply outdated or even funny. However, as I learned more about the history behind these media, I realized how deeply ingrained anti-Black stereotypes were and how normalized they became in mainstream entertainment. For instance, many cartoons and theater shows before the civil rights movements heavily relied on exaggerated Blackface tropes and minstrel portrayals. These representations not only distorted Black identities but also perpetuated harmful stereotypes that influenced public perception. It was striking to see how such imagery was casually accepted and even enjoyed by younger generations, contributing unknowingly to a cycle of stereotype reinforcement. I remember studying August Wilson’s work in a theatre history class, where we discussed how his plays challenge these old narratives by bringing authentic Black voices and experiences to the forefront. Before Wilson, Black representation was often reduced to caricatures or met with violent backlash, such as the historical accounts of white riots opposing Black theatre troupes performing classics like Shakespeare in New York City. Recognizing these Blackface tropes today is essential—not only to call out racism when encountered but also to educate ourselves and others. Without this awareness, many of us might unintentionally repeat or perpetuate these tropes, leading to cultural gaslighting wherein the Black community’s experience and reality are invalidated or ignored. In daily life, this means being critical of the content we consume and share. From childhood cartoons to vintage theatre, these portrayals affect how societies view race and identity. It’s important to identify the subtle and overt messages embedded in historical media and to engage in conversations about their negative impact. By doing so, we contribute to a broader cultural understanding and help dismantle the normalization of anti-Blackness. Personally, this journey has been eye-opening and has emphasized the importance of preserving authentic storytelling while challenging and learning from past mistakes in media representation.