2. DIANE KEATON AS ANNIE HALL IN ANNIE HALL (1977)

This is the movie that practically invented the modern romantic comedy, before the genre gained such a negative stigma among film fans. People may not remember every line from the flick or every fourth-wall breaking joke that Allen tells, but one thing everyone comes away with is the urge to date Diane Keaton. Keaton played the titular Annie Hall and introduced the mainstream world to the type of ditsy, quirky leading lady that became Allen’s signature.

Keaton’s greatest asset wasn’t her body or overbearing sex appeal, it was her offbeat demeanor and realistic good looks. Out of all of Allen’s other leading ladies, Keaton conveyed the type of girl we would all like to take out. She seemed fun, easygoing, and real. It’s one of those rare movies where the romance not only feels grounded, but the lead actress actually seems attainable. Though, let's not kid ourselves.