“What am I supposed to do with all these white people?”

This chapter traces the development of the gentrification narrative and the “gentrifiers’ gaze” in 50 years of film and television, from Hal Ashby’s The Landlord (1970) to a number of recent prestige television series, including Insecure, High Maintenance, and Flatbush Misdemeanors. While gentrification narratives have appeared in one-offs and cycles in previous decades, gentrification now regularly determines narrative trajectories, creates interpersonal conflict, and shapes characters’ lives in contemporary television. Through textual analysis of several exemplary episodes, I show how these series reflect millennial gentrification anxiety, or the sense among the increasingly transient urban dweller that one is constantly at risk of both displacing others and being displaced, due to the precarity of gig work and the service economy. Significantly, these series have also become more reflexive about the role that creative workers and media/tech industries play in driving urban change. I argue that this self-reflexive interrogation reflects the series creators’ recognition of, and ambivalence toward, their own complicity in transforming the communities they seek to represent onscreen.