This chapter is devoted to George Orwell’s compelling and still-influential masterpiece of dystopian surveillance. It deals with Nineteen Eighty-Four’s dominant and unique place in the public imagination, while considering how surveillance theorists have dealt with the novel. It also traces connections between Nineteen Eighty-Four and previous utopias, showing how Orwell’s ideas were in different ways influenced by writers such as H.G. Wells, Jack London, Yevgeny Zamyatin, and Aldous Huxley. The chapter then presents a reading of the novel that stresses new ways of interpreting the treatment of surveillance, emphasising the limitations of monitoring in the novel: how the proles, who make up 85% of the population, are largely left alone, and how the countryside is a space seemingly surveillance-free. It also examines the distinct characters of Winston Smith and Julia, noting that, despite having lived under Party control all her life, when Winston meets Julia she is already consciously resistant to the putatively totalitarian ideology. The chapter also addresses the surprising extent and nature of resistance that Winston puts up, even in a world terrorised and warped by the Thought Police, telescreens, Newspeak, the Party, and Big Brother. Despite its efforts, the Party never really gets ‘inside’ Winston’s head in the sense of knowing his thoughts, reducing him to a compliant shell at the end of the narrative a hollow victory that marks the failure of Oceania’s surveillance regime.