What it's about: After graduating college in Chicago, two strangers get roped into carpooling all the way to New York City together. They don't get along. As the years go by and they enter adulthood, Harry and Sally keep bumping into each other and form a unique bond.
Why it makes the list: Written by Nora Ephron (Sleepless In Seattle, You've Got Mail) and directed by Rob Reiner (Stand by Me, The Princess Bride), When Harry Met Sally... remains one of the most beloved romantic comedies of all time. It's precisely what a rom-com should be: The dialogue is smart and witty, the characters feel relatable and dynamic, and it perfectly depicts the journey of a slow-burn romance.