Bonus: When Harry Met Sally (1989)
Director: Rob Reiner
Writer: Nora Ephron
Cast: Billy Crystal, Meg Ryan, Carrie Fisher
Yes, technically this one is not a ’90s rom com since it came out in 1989 — but it inspired and fueled the ’90s rom com boom. (It also earned the great Nora Ephron a nomination for Best Screenplay at the 1990 Oscars, so that counts for something, right?)
When Harry Met Sally is the end-all-be-all of will-they-won’t-theys. It follows Meg Ryan as Sally and Billy Crystal as Harry from the time they meet after graduating college through 12 years of chance run-ins and awkward romantic interactions. Just when you think they’ll finally end up together, they don’t — and just when you think they’ll finally call it quits, they surprise you.
Main image: Meg Ryan during the most famous scene in When Harry Met Sally. Columbia Pictures.
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