When it comes time to disagree that White male privilege exists, insisting race and gender equity is already achieved, deniers often point to prominent people of color in sports and entertainment industries. Famous figures like Oprah Winfrey, Beyonce Knowles, Jay-Z, and Lebron James may, with cursory glance, give impression that—even if fields like finance, technology, medicine, law, and politics have glass ceilings—the entertainment field provides a seemingly utopian space where the playing field has already been leveled, and the so-called American Dream of race and gender equality has assumedly arrived. Using both quantitative and qualitative data, from primary and secondary sources, we look beyond token big names to overall patterns in music, professional sports, and film arenas to document how racial and gender inequality continue to stratify entertainment industries. Our analysis demonstrates that women and people of color are conditionally accepted, at best, to entertain, provided they stay in their proverbial place—seldom owning, directing, or taking the lead, and penalized when speaking out about oppression. We end with recommendations on how to shatter glass ceilings, like inclusion riders and Rooney Rule, along with other ways to bring more women and people of color into more powerful positions in these industries.