There was a period where Meg Ryan was just pumping out the best romantic comedies of all time, and we're pretty sure it started with When Harry Met Sally. This is a film that doesn't age (unless you count the dorky, late '80s clothing). The story remains timeless, no matter when you watch it, or who you watch it with. Released in 1989, this film also stars Billy Crystal.
Written by Nora Ephron and Rob Reiner, When Harry Met Sally was thought to be quite unique at the time, as it was created by a male-female team. The story follows Harry (Reiner) and Sally (Ryan) over a period of twelve years in New York City. The pair meet various times in chance encounters throughout the years and develop a friendship before predictably falling in love at the end.