7. Annie Hall (1977)
Annie Hall wasn’t Woody Allen’s first feature by any means, but it did firmly establish the template the prolific filmmaker would continue to work from ever since, and still does up to this day.
Allen wrote the title role specifically for Diane Keaton, and she rewarded his confidence with an Academy Award winning performance, while the movie itself also picked up gongs for Best Picture, Best Director and Best Original Screenplay.
The tone and style of Annie Hall became hugely influential in American independent cinema over the next decade, but nobody hit the sweet spot between heartfelt romance and downtrodden self-awareness better than Allen did in what’s arguably his best ever movie.