#23 Annie Hall (1977)
This movie is the ultimate portrayal of romantic deconstruction ever written. Allen plays Alvy Singer, a New York comedian who falls in love with Annie Hall, played by Diane Keaton, who is a mid-western aspiring singer. As intelligent and poignant as it is humorous and memorable, this film uses a great many techniques to push it far past the boundary of romantic comedy. Uses meta-cinematic moments to break the fourth wall, Allen addresses the audience and sometimes pulls people into scenes just to prove a point, before shoving them off screen. The chemistry of Keaton and Allen onscreen is truly something to be marveled. The story of their relationship occurs out of order, shifting from present to past to future. I’ve always admired Allen’s ability to make his movies far more realistic than all the others, and his bravery at not taking the “happily ever after” approach to his films, because nothing in life ever works out that way, so I applaud his honesty towards his audience. I wanted to choose Whatever Works because of the pessimistic protagonist, but after some thought, I’d have to pick Annie Hall as Woody Allen’s best work which deserves to be on my Top 30 Favorite Films, in at number 23.