The #OscarsSoWhite twitter campaign started a major conversation in the 2010s about diversity at the Academy Awards, and Hollywood more broadly. However, the moment was just the latest in a long history of media discourse responding to the event. This paper examines the news coverage around the first two Black performers to receive awards “buzz”: Louise Beavers in Imitation of Life (1934); and Hattie McDaniel, who became the first person of color to win an Academy Award for her performance in Gone With the Wind (1939). Beavers, who ultimately did not receive a nomination, had been the first potential Black contender at the event; nonetheless, her snub facilitated a dialogue about the systemic exclusion of minority groups at the Oscars that continues today. As the first Black winner, McDaniel fueled a wider exchange about what the moment would ultimately mean for progress on screen. McDaniel had broken barriers, but did that actually accomplish anything? This paper focuses on the symbolic meaning of the Academy Awards trophy and how its allure as Hollywood’s most coveted achievement has often been used as a symbolic gesture without any long-term substance. At the same time, the modes of discourse around the event has motivated conversations and pushback exposing the wider systemic realities of the American film industry. This paper looks at the origins of Black media discourse around the event, and how they persist into the contemporary context of the Academy Awards.