1. When Harry Met Sally
Annie Hall redefined an entire genre. It set the groundwork for the modern day romantic comedy. When Harry Met Sally took that frame and laid the foundation that is todays romantic comedy. It features a likable everyman in Billy Crystal, a cutesy likable woman in Meg Ryan, two sidekicks that bicker and the ever agonizing question of whether or not the two will ever get together. If you hate what you see today, blame this film. But, you cannot doubt that it did perfect it and that it is worth imitating. The film asks the question of whether or not you can be friends with someone without romantic interest interfering. And as with the rest of the list, the common theme amongst all these films is that each film is genuine in what it has to say about relationships. A friendship grows gradually. A loving relationship also grows gradually. You see throughout the film the gradual growth of the romance and it makes sense unlike a lot of other romantic comedies. Rob Reiner takes its time in getting its characters together and it spans years and years instead of a vacation on a villa like more mediocre films. That is why When Harry Met Sally is the ultimate romantic comedy.