7. Pretty in Pink (1986)
Director John Hughes is a sucker for a happy ending, and Pretty in Pink, resonates with fans because of Hughes’ transparent affection for underdogs.
Andie (Molly Ringwald) is poor, but she’s got her own unique sense of style. She’s the girl who’s way too cool to peak in high school, so she’s just putting in her time until she gets out. Blane (Andrew McCarthy) is rich, but a sensitive guy who appreciates what Andie brings to the table.
Considered a Brat Pack film, Pretty in Pink features a bunch of wealthy snobs led by James Spader (what 18-year-old wears linen suits to school every day?) and poor pierced weirdos from the wrong side of the tracks who have no legitimate reason to dislike each other.
Talk about oversimplifying the social hierarchy of the American high school. The obstacle Andie and Blane must overcome is a disparity in socio-economic status.
Rounding out the cast is film legend Harry Dean Stanton (Twin Peaks) as Andie’s well-meaning but depressed father, and Annie Potts (Designing Women) as a super-sassy record store manager who’s also Andie’s boss, confidant, and sole maternal figure.
HuffPost put the Pretty in Pink soundtrack as part of its 15 Film Music Compilations That’ll Change Your Life list
Pretty in Pink lacks the originality of Sixteen Candles and The Breakfast Club, but Hughes infuses just enough unique elements like Jon Cryer’s (Supergirl) impressive lip sync performance to Otis Redding, a particularly smarmy turn by Spader as Steff (often imitated but never duplicated) and Ringwald’s signature pout to churn out one of the best teen movies ever made.