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The enduring popular image of James Bond is (in the words of the theatrical trailer for Dr No) ‘the gentleman agent with the licence to kill’. Yet the screen Bond is hardly a hero in the manner of gentlemanly archetypes such as Cary Grant and David Niven (reputedly Ian Fleming’s preferred choice for the role). This chapter will explore how the image of Bond in the films has changed over time both in response to wider social and cultural archetypes of masculinity and due to the different performance styles of the various actors to play the role: Sean Connery, whose rough-hewn Scottishness can be seen as a means of representing the ‘otherness’ of Fleming’s character (‘Bond always knew there was something alien and un-English about himself’); George Lazenby, whose one-off appearance as an emotionally damaged Bond in On Her Majesty’s Secret Service anticipated later portrayals of the character; the parodic variant of Roger Moore; the brooding Byronic hero of Timothy Dalton; the ‘Milk Tray Man’ charm of Pierce Brosnan; and Daniel Craig, whose combination of bull-in-a-china-shop physicality and vulnerable masculinity (literally so in Casino Royale) has by common consent successfully transformed Bond from a cartoon superman into a twenty-first century action hero.