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Revisiting Some Kind of Wonderful (1987) 36 Years Later

I recently wrote about my favorite rewatches of 2023, movies I hadn’t seen in at last five years. While it doesn’t break my 2023 record of most years between watches (at 44 years, Alligator wins that distinction), I watched Some Kind of Wonderful recently for the first time in 36 years. While I wouldn’t call it a great film, there’s something about it that speaks to me. I found the movie on DVD at a thrift store some time back and about a month ago added it to my “Watch it, then get rid of it” stack. Now that I’ve rewatched it, I think I’m going to keep it.


Some Kind of Wonderful, written by John Hughes and directed by Howard Deutch, is essentially a remake of Pretty in Pink (1986), also written by Hughes and directed by Deutch. If you’re wondering why Paramount would release Some Kind of Wonderful so close on the heels of Pretty in Pink, it’s because Hughes was such a bankable property for teen movies, the studio didn’t think audiences would know or even care about the similarities. These movies were fun and smart, created by people who seemed to understand teenagers and refused to treat them as brainless stereotypes. Consequently, teens flocked to these pictures.

At their core, both Pretty in Pink and Some Kind of Wonderful are romantic movies about kids from different socioeconomic classes falling in love, or at least attempting to. In Pretty in Pink, Molly Ringwald plays Andie, the girl from the wrong side of the tracks who falls in love with rich boy Blane (Andrew McCarthy). But the guy who really loves Andie is her quirky friend Ducky (Jon Crier), who provides some of the film’s best moments.

Some Kind of Wonderful switches the roles with Eric Stoltz as Keith, the working class kid who falls for the beautiful rich girl Amanda Jones (Lea Thompson). Keith’s best friend is Watts (Mary Stuart Masterson), a girl from a broken home whose passion (besides Keith) is playing drums. (I can’t even begin to tell you how many girls signed up to play drums when I was a band director after the film was released.)

We all know the plot, which goes back to Shakespeare and probably way before that. (Maybe that’s why they teach Romeo and Juliet to kids in the 9th grade: “Hey kids, this isn’t new. You’re not the first to deal with this stuff.”) But it’s still a good story.

Watts is cynical and not one iota interested in fitting in with the cool kids. Keith’s an outsider content to quietly pursue his art, despite his dad urging him to apply to a college where he can earn a degree that will help him in the “real” world. Keith and Watts could easily become cardboard caricatures, but Hughes allows them to ask questions, to be as smart as teenagers really are, yet show us that they don’t have all the answers, although they don’t want you to know it.

Keith is naive, a fool for a pretty face, but not just any pretty face. Amanda does it for him, but he’s way out of her league. There’s a pecking order in high school and it can be cruel. (Maybe you remember.) But Keith is willing to make the attempt to break through those barriers. And although Amanda knows she’s on a treadmill of emptiness, she’s either unwilling or unable to look very far beyond herself.

We often forget that attending high school is like living in a small town. You know everyone, everyone knows you, and even worse, everyone sees and evaluates everything you do, either according to their own standard or the standard of the firmly-established cliques. Think back a few years (or, in my case, decades). Think about that girl or guy you really wanted to hang out with, but they were unapproachable. Maybe they had more (or less) money than you, had a nicer (or less nice) house than you, more fashionable clothes, a better car, etc.. If you made a move across those lines, there were most likely consequences. People talk even if they don’t confront you, which is sometimes worse. Keeping things as they are is safe, but it’s often boring, and maybe even heartbreaking. Watts longs to keep Keith from hurt, yet her own bruises from unrequited love seem never-ending.

I saw a lot of kids like this from a distance when I was a band director. You see a lot of pain and hurt, but you can’t really do much about it. Sometimes kids will come to you with their problems. When you’re a band director or a coach, you often teach the same kids for several years. You get to know them and they often share their stories with you, but sometimes they do things that hurt themselves or others as they’re trying to sort things out. During my first year of teaching, one of my students was constantly a behavior problem in class. A wise mentor told me, “It’s probably not about you at all.” He was right. That student had a lot of awful things going on in his life.

Most of John Hughes’s films are about teenagers, not because they’re bankable (although they were then and are now), but because they’re trapped inside an in-between world: they’re no longer kids, but they’re not yet grown up. Maybe you remember the feeling. I do. Rewatching this movie brought all of those feelings back, the bad and the good.

Speaking of the good, one of my favorite scenes in the film occurs when Watts informs Keith that he should be ready for his first kiss with Amanda on their upcoming first date. Keith demurs, but Watts tells him he can practice on her if that’s not too much of a hardship for him. They dance around this issue for a bit, Keith hesitant, Watts hopeful, then Keith finally kisses her. The moment blows Watts’s mind, partly because she’s already in love with him, but more importantly this dream-come-true event propels Watts beyond anything she could have imagined. Is this because Keith is such a great kisser? Are his true feelings emerging? Are hers more powerful than she suspected? Or is Keith’s desire for Amanda being transferred to Watts? I’ll let you be the judge:

The film’s ending is not exactly realistic, but it is satisfying, even 36 years after decades of lives filled with the disappointments, cynicism, and the realities of adulthood. High school (thankfully) is long over, and although we sometimes transfer life into some of those same confining compartments and social groups, we should congratulate ourselves that we have escaped, hopefully with people who are there for us day after day, year after year. I hope we never completely lose that innocence, that longing and appreciation for someone who understands us. Hughes knew that longing and was able to convey it in movies that still hold up decades later. Some Kind of Wonderful is one of them.

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Thanks Andy, I couldn't agree more. My crush on MSM lasted for years!

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Many thanks, Jeffrey. I feel the same way about MSM!

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