1. Annie Hall (1977)
Academy Award nominations: 5, for Best Picture, Best Director (Allen), Best Actor (Allen), Best Actress (Keaton), Best Original Screenplay (Allen, Marshall Brickman).
Wins for Best Picture, Best Director, Best Actress and Best Original Screenplay. Allen's Best Picture-winning masterpiece remains the high-point of his career, and one of the best American films ever made. Allen knocks us out with an unconventional structure that in lesser hands might seem messy, but rather, Alvy Singer's (Allen) stream-of-consciousness, fourth-wall-breaking exposition only serves to layer on the charm even thicker in this daring and devastatingly honest film about romance that remains hugely relevant today. Allen's account of the inner workings of contemporary relationships remains unrivalled even today, understanding humans on an inner level that most films can only dream to aspire to; it is a film almost all of us can connect with on some level. The film also marked Allen's move away from straight-up comedy towards more considered, existential dramatic comedy, as has been a staple of his career ever since. If you haven't seen it, why not?