Although I was a teen in the 80s, it doesn’t mean I saw every teen movie released then. Especially teen romantic comedies. Although I adore the quartet of John Hughes initial directorial efforts (Sixteen Candles, The Breakfast Club, Weird Science, Ferris Bueller’s Day Off), I never saw the two teen movies he wrote and produced (but let Howard Deutch direct) around the same time: Pretty in Pink and Some Kind of Wonderful.
Having recently watched both films for the first time as an adult, I sadly found both films lacking sympathetic characters or reasonable conclusions. Most of all, I saw how much they are exactly the same film.
Pretty in Pink (PIP) has the benefit of the better cast and being the better film. Beyond the 3 leads (Molly Ringwald, Andrew McCarthy, Jon Cryer) is the top notch cast of Harry Dean Stanton, Annie Potts, and James Spader as well as cameos from Gina Gershon, Kristy Swanson, and Andrew “Dice” Clay. Some Kind of Wonderful (SKOW) has the lighter weight trio (Eric Stoltz, Mary Stuart Masterson, Lea Thompson) and a less interesting supporting and cameo cast of Elias Koteas, John Ashton, Candace Cameron, and Chynna Philips. Otherwise the differences are minimal.