When Harry Met Sally... (1989)
Director: Rob Reiner
Screenwriter: Nora Ephron
Stars: Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby
When Harry Met Sally... explores two subjects the right (i.e. not obnoxiously like Katherine Heigl rom-coms): Can (heterosexual) men and women just be friends? And, is there anything more hilarious than Meg Ryan faking an orgasm in a Jewish deli?
Besides giving pop culture one of the most beloved (and starkly realistic) couples ever, this movie perfectly packaged a then-hard-to-define romantic situation: To this day, people still describe their friend-zoning as being "stuck in a Harry-and-Sally relationship." —TA