This is the first book-length study to focus on James Bond's relationship to the playboy ideal during the sixties and beyond. The book examines aspects of the Bond phenomenon and the playboy lifestyle, best represented in the pages of Playboy magazine, and considers how they are interconnected, especially in terms of gender and consumption, to construct and reflect a powerful male fantasy in the post-war era onwards. This analysis of the close association and relations between the emerging cultural icons of James Bond and the playboy is particularly concerned with Sean Connery's definitive Bond as seen in the films and promoted and used by the media. By exploring the connections between Bond and Playboy within the historical framework and contemporary debates, this book offers new insights into the related phenomena and their enduring legacy in popular culture. Throughout, the book traces and analyses key aspects of the development of James Bond's connections to the lifestyle fantasy and image of the playboy. These connections are rooted in the fifties and were formalised in Playboy during the 1960s with the help of Ian Fleming and his Bond novels, followed by the rising popularity of the big screen character first played by Connery, which established other associations that still remain influential today. This book will contribute to the growing area of Bond studies as well as to the study of popular culture, and will interest scholars and students in these and other fields of research.