Aesthetic and political representation are often treated separately, but this book argues that film offers a unique perspective through which to understand the dangers to equality and freedom that lurk in representative politics. The potential problems of representative democracy have long been debated: does it cultivate apathy and discourage citizen participation? What does it mean to be faithfully or well represented in a democracy? And how can appropriate, meaningful representation be achieved? Here, these questions are addressed from a new perspective. Representation, Joshua Foa Dienstag argues, can create the illusion of freedom and reciprocity in place of the real thing, and in both cinema and politics, what gives us pleasure is not the same as what secures or supports our existence as free and equal citizens. As this book shows, there are political dangers not visible within the current debates around democratic representation, dangers we can better understand and help to minimize by considering the way that human beings interact, emotionally, with their filmic representations. Dienstag looks at a series of films that directly confront issues of representation (Her, Blade Runner, The Man Who Shot Liberty Valance, Melancholia, and the Up documentary series) to diagnose these hazards and consider how best to respond to them. Each chapter looks at a specific film as emblematic of a different conception or problem of representation often ignored by mainstream political debates (such as reciprocity, happiness, boundaries, evil) to show that the relationship between representation and freedom is fraught with tension. This book continues Dienstag’s earlier groundbreaking work on philosophical pessimism, understood not as something despairing, but as a rejection of the idea that these necessary tensions can be cured. Ultimately, Dienstag seeks to defend a kind of pessimistic politics that might produce a better sort of democratic representation than what we have today.