Not all is lost though, because Keith shares detention with a handful of troublemakers, including resident bad boy Duncan (a hilarious Elias Koteas). He’s also smitten enough with Amanda that he paints her portrait (okay, a little creepy), and purposely pulls a fire alarm to get detention when he thinks he’ll be sharing it with her, unaware that she’s used her female charms, in a rather icky scene where she flirts with the assistant vice principal, to get out of it. On the other hand, Keith, though car-less, is earnest and sweet, seemingly the perfect guy to help Amanda realize she’s too good for the shallow, mean spirited popular crowd she’s been running with.
He’s full of cocky entitlement and not much else, which makes you wonder what Amanda saw in him in the first place – other than the nice car and social acceptance that would come with dating him. Like most wealthy a-holes in ’80’s teen dramedies, Hardy Jenns not only has the proper jerky name (“Hardy Jenns with two n’s”), but he has perfectly coifed floofy hair and a wide variety of blazers in various colors. Heck, he’s not even slick about it, hitting on girls right in front of Amanda, and then gaslighting her to make her feel guilty for not trusting him. Oblivious to her affections, Keith finds himself attracted to Amanda Jones ( Lea Thompson), a beautiful girl whose popularity stems from dating the handsome and wealthy Hardy Jenns ( Craig Sheffer), who also happens to be a jerk who cheats on her, and often. He works in an auto garage and is best friends with a girl named Watts ( Mary Stuart Masterson), a tomboy who loves to play drums and is secretly in love with him. Keith ( Eric Stolz) is a senior in high school with no real clear plan for college, despite the pressure put on him by his dad. In any case, it’s kind of a shame that there’s not more love for Some Kind of Wonderful because I think it’s the superior movie. That may be because Pretty in Pink featured some Brat Pack regulars in Molly Ringwald and Andrew McCarthy (both of whom were also offered roles in Some Kind of Wonderful), or maybe it’s because Pretty in Pink was released a year before Some Kind of Wonderful. But it’s Pretty in Pink that tends to get the attention and love, while Some Kind of Wonderful is often shunted to the side. Both are about school misfits falling for the popular student while their best friend secretly pines for them.
There is also the fact that the premises are pretty similar as well. That’s not terribly surprising given both movies were written by John Hughes and directed by Howard Deutch.
Some Kind of Wonderful is often described as a gender reversal of Pretty in Pink.