59. Pretty In Pink (1986)
Directed by: Howard Deutch
Starring: Molly Ringwald, Jon Cryer, Andrew McCarthy
Synopsis: Two high schoolers from different economic and social circles attempt a relationship.
This is an incredibly romantic moment and you’re ruining it for me! - Jon Cryer as Duckie.
I was surprised to see who the director was. Who is Howard Deutch? Turns out he also directed Some Kind of Wonderful which is another John Hughes film that is good but didn’t quite make my list. This one, a “Brat Pack” classic , certainly does. The plot is as old as time but it’s fun anyhow. All of the leads are excellent, particularly Cryer who was never this good again.
Credit to Hughes for including an appearance by one of my favorite 80s bands, the Rave-Ups, apparently at the insistence of Ringwald who was dating the lead singer at the time. However, the title song is a remake by the Furs; the original single from 1981 has always sounded better to me.