This article compares and examines Reputation and Homecoming, two long-form videos of 2018 performances by Taylor Swift and Beyoncé Knowles, respectively. The videos have much in common, as both were released via Netflix in 2019, and both document important milestones in the career success of two female solo artists. Moreover, the subjects of these videos have risen to the top of an industry that has not traditionally rewarded their gender, nor allowed them to headline at these types of events—a stadium in the case of Swift; a multi-day/act festival, in the case of Beyoncé. In Homecoming, Beyoncé uses her headliner status at Coachella to pay homage to deep cultural traditions of a non-white world; when considered alongside it, Reputation reveals inconsistencies in Swift’s presentation of herself as an authentic artist in charge of her own creative and career choices, and these cracks are complicated by a second documentary, Miss Americana, in which her thralldom to a conservative ideology becomes even more visible and problematic, even to herself. Viewed together, the films provide a prism through which we can reflect on serious changes regarding both race and gender in America, and the ways that they are exhibited in live performance and popular culture.