Title: Some Kind of Wonderful
Released: 1987

Fix: 1980s, teen movies, John Hughes, gender-swapped Pretty in Pink, bad financial decisions, precocious kid sisters
Amazon Prime

Amazon Prime Summary:

In this story from legendary filmmaker John Hughes, Keith, Watts and Amanda prove that you’ve got to risk a broken heart in order to find your one true love. This unforgettable romantic comedy has laughs, romance and is truly Some Kind of Wonderful.

FYA Summary:

In this underappreciated story from legendary filmmaker John Hughes, Keith is a sensitive, soulful kid from ~across the tracks~ who can’t decide what he hates more: his low-class upbringing or the rich, popular kids at school. The only things he doesn’t hate are art and his best friend, tomboy drummer Watts. Oh, and Amanda Jones, the beautiful, popular girl with the piece of shit boyfriend. He loves Amanda Jones to an almost creepy degree. He gets up the nerve to ask her out on a date at the exact moment she’s trying to make her boyfriend jealous, so she says yes. Keith spends the rest of the movie planning the world’s most expensive, over-the-top date to impress Amanda Jones, and comes to some serious revelations about what (or perhaps who?) he really wants. 

Familiar Faces:

Eric Stoltz in Some Kind of Wonderful

Eric Stoltz as Keith

I know this might come as a shock to some of you, but Eric Stoltz used to be hot AF. Like…look at his face? He was extremely pretty. If you’re like, “I don’t recognize this beautiful face?” it’s because Eric Stoltz somehow got way less beautiful after this movie. RIP. You may have seen him playing the boring AF John Brooke in Little Women, or maybe you know him as Rocky from Mask. He plays “creepy guy” in “all movies.” Eric Stoltz has been in everything but I feel like he had a very short window to play a romantic hero and this was basically it. 

Mary Stuart Masterson in Some Kind of Wonderful

Mary Stuart Masterson as Watts

Mary Stuart Masterson is incredible in everything. I mean, have you seen Fried Green TomatoesBenny and Joon? As Watts, she’s perfect and completely ahead of her time, giving a leather-clad middle finger to gender norms. She wears cool fringe gloves and even cooler mis-matched earrings, but you know, it was the 80s so her short hair and leather vests are supposed to scream: WEIRDO OUTCAST. She keeps Keith real, or at least she tries, delivering cutting one liners like, “Oh, you wanna start a book club with her?”

Lea Thompson in Some Kind of Wonderful

Lea Thompson as Amanda

Coming in hot after the first Back to the Future movie, Lea is the picture of girl-next-door perfection, but unlike some of the other popular girls from 80s movie, she has a surprising amount of depth. (BTW, in writing this post, I learned that she is Zoey Deutsch’s mother?! Am I the only person who didn’t know that?)

Couch-Sharing Capability: Solo Kind of Wonderful

Unless your significant other is into B-list 80s teen dramas starring the most Pisces dude that ever lived, you’re enjoying this one on your own. 

Recommended Level of Inebriation: Stay Sharp

This movie is filled with incredible quips and one-liners that sometimes get lost in the melodrama. Stay sharp if you want to catch them all.

Use of Your Streaming Subscription: Throwback Thursday

I was obsessed with this movie in high school (confession: I used to listen to the song that played during The Kiss on repeat). I was always preaching the word that this was one of the most underrated John Hughes movies of the era. If you’re going to do a Brat Pack deep dive, this one ranks right up there with the Molly Ringwald trio.


Rosemary lives in Little Rock, AR with her husband and cocker spaniel. At 16, she plucked a copy of Sloppy Firsts off the "New Releases" shelf and hasn't stopped reading YA since. She is a brand designer who loves tiki drinks, her mid-century modern house, and obsessive Google mapping.