27. Pretty In Pink (1986)
John Hughes knew exactly how to cater to his target audience, and cult classic Pretty in Pink very much follows the typical Brat Pack formula right down to a tee.
Teen icon Molly Ringwald stars as a high school outcast that starts dating one of the popular kids, which causes plenty of tension in her personal and social lives, not least from her best friend.
Jon Cryer plays the quirky pal who harbors a secret affection for the heroine, and while Pretty in Pink hardly breaks new ground from a narrative point of view, writer Hughes and his cast make everything grounded and relatable no matter how many times we’ve seen the scenario play out in the past.
