This article conducts a digital cultural analysis of memes associated with Living While Black and the figures “Becky” and “Karen,” showing how these artifacts function as forms of social commentary and racial critique. Using visual Critical Technocultural Discourse Analysis (CTDA), Williams demonstrates that these meme genres call attention to patterns of racialized surveillance, control, and casual racism enacted by White individuals and institutions, particularly in public spaces. Rather than merely representing incidents of entitlement and discrimination, the memes reframe such behaviors as part of enduring power structures, enabling Black creators and audiences to reclaim narrative control and express collective resistance.