1. Alfie (1966)
Alfie is both an incredibly witty comedy and a tragic tale of loneliness. That it succeeds at either of these is an incredible feat given that, on the face of it, the titular bachelor is incredibly unlikeable (to the extent where he makes Ferris Bueller look like a saint). Alfie is a misogynistic sex pest who insists on referring to women as it; a more real world, latter day Barney Stinson. It is thanks solely to Michael Caine and his constant fourth wall breaking that we not only put up with him for two hours, but are happy to do so. It is a film that has clear influence on most of the other films on this list. At the start, he makes reference to the films lack of opening credits; a nod to convention similar to The Muppets style. And yet it manages to showcase the most self-assured breaking of the fourth wall and in the most interesting way. While, like Ferris, the constant turning to the audience (often with surprise at us watching) provides humour that helps us settle in and feel close to the character, in this case its also used for something else. A lot of the inner-monologues to the audience occur around Alfies more promiscuous moments and are clearly the completely honest thoughts of the character. He may be justifying his actions, such as casually leaving women when they become too clingy, to us, but the main purpose of it is to get it straight in his own mind. To Alfie, we are his conscience; we, like him question the sleaziness of his actions, but Caines natural charm convinces himself it is OK. This gives a real payoff to the emotional tragedy of the abortion and the gradually stripping away of Alfies life. When he finally starts to see the beauty in a womans nature and laments his lack of peace of mind we know he is sincere and feel the emptiness because we are now part of him. All that aside, it also allows for some cracking moments; rolling his eyes when a woman doesn't see where things are going and best of all, the immortal line, Marvellous what you can get on the National Health, innit. Brilliant, know what I mean?