4. Annie Hall (1977)
Perceived by many as a huge influence on
(500) Days of Summer,
Annie Hall is a similarly intelligent, hilarious and sublimely-acted romantic comic drama, and for our money, is Allen's best film to date. The film begins with comedian Alvy Singer (Allen) looking back on his relationship with the titular Annie (Diane Keaton) and wondering where it all went wrong. In flashbacks, we see how their relationship began, full of youthful optimism and enjoyment, but again, like the aforementioned film, we know from the start that it is doomed, and we are merely watching how it took such a dramatic nosedive. Love blossoms, but of course, differences soon emerge as things get more serious and the two move in together, causing Alvy to question the very nature of love and relationships, and eventually, the two break up. In the wake of this, he tries to date other women, but finds the experiences humiliating and depressing. After a brief reconciliation with Annie, the two again decide it isn't working, and move onto other people. Much like (500) Days of Summer - and in a scene that surely influenced it directly - the two meet again at the film's close, moved past their relationship, and hoping to see what the future brings. Allen's films are known for the emotional honesty, and no better is that realised here than in a film that has influenced the genre ever since, though has never quite been matched in its intelligence and strong characterisation.