Abstract
This chapter begins by identifying 1965 as a highpoint for James Bond and also a significant milestone in both the formal and informal relationships that developed between Bond and Playboy. It is the first of three chapters to use as a key point of reference the 1965 November issue of Playboy, which included an interview with star Sean Connery. The chapter examines how Playboy endorsed Connery’s Bond as a contemporary role model both in the early Bond films and beyond the screen, and as an iconic embodiment of the playboy fantasy ideal. It examines how particular aspects of Connery’s Bond resemble the 1960s Playboy fantasy of individualism, social mobility and the work–leisure relationship, which was not without its contradictions and paradoxes.
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