What is the American dream, and why has it proven so elusive for many people? By examining popular culture’s portrayal of the dark side of the American dream, this book seeks to answer these questions. Only when we see people fail in their pursuit of the American dream do we begin to understand its limitations and its inner contradictions. This book explores five representative examples of the American dream gone awry: (1) Huckleberry Finn; (2) the films of W. C. Fields; (3) the Godfather films;(4) Breaking Bad; and (5) The Walking Dead (and other “end-of-the-world” narratives). As these cases suggest, America, as the fresh-start nation, always threatens to become the land of the false start. America gives its people the freedom to reinvent themselves, but that easily turns into a license to imposture. The American ideal of the self-made man is shadowed by the specter of the con man, and the line between legitimate business and criminal activity sometimes becomes hard to draw clearly. Although the American dream is to achieve success in both family and business, the Godfather films and Breaking Bad show these goals tragically at odds. With its Hollywood endings, American popular culture is often thought to be naively optimistic; this book demonstrates that film and television creators have been capable of raising thoughtful questions about the validity and viability of the American dream, thus deepening our understanding of America itself.