In 1987, fresh off the success of Pretty in Pink, John Hughes offered audiences another teen love story: Artistic outcast Keith (Eric Stoltz) pines for the most popular girl in school, Amanda Jones (Lea Thompson), while failing to notice that his best friend, Watts (Mary Stuart Masterson), is hopelessly in love with him.

Shot on location in San Pedro, California and throughout Los Angeles, Some Kind of Wonderful marked a departure for Hughes – moving beyond his beloved midwestern settings to the sunnier climes of California and a quieter, more heartbreaking take on adolescent romance (though his penchant for rocking soundtracks — this one heavily influenced by The Rolling Stones — remains).

Off-screen, it kick-started a romance between star Lea Thompson and director Howard Deutch, who have been married since 1989 (and are the parents of a current rom-com princess, Set It Up’s Zoey Deutch). Thirty-two years later, the director and cast reflect on the making of the film.

Image zoom Joyce Rudolph/Paramount/Kobal/REX/Shutterstock

Some Kind of Wonderful started as a much different project for Hughes, a broad comedy about a boy’s date with the most popular girl in the school. Before shooting began, the script went through several iterations and casts. Director Howard Deutch (Pretty in Pink) left the film and was succeeded by Martha Coolidge, who was eventually fired, along with some principal cast, and replaced once again by Deutch.

HOWARD DEUTCH (Director): When I was in editing on Pretty in Pink, John suggested we talk about it. I wanted Molly [Ringwald], and she turned it down. She thought it was too much like Pretty in Pink. He wrote a script that was about a date, very funny, and I offered [the role] to Michael J. Fox. It was a perfect part for him, and he passed.

LEA THOMPSON (Amanda Jones): I was offered the role in Some Kind of Wonderful when it was a different script. I turned it down because I knew the other girl’s part was so much better.

DEUTCH: [The fact] that I couldn’t cast was not received well by Paramount, so they hired a different director, and John Hughes rewrote the script and made it less of a comedy and more of a drama.

MARY STUART MASTERSON (Watts): The first draft was comedically more broad. As we worked on it, it became a little bit more what it is now, which is more similar in tone to Pretty in Pink, a little more earnest and less broad comedy.

ERIC STOLTZ (Keith Nelson): We had rehearsed for quite some time with a different cast. We’d spend a lot of time trying to figure out how to tell the story visually without so many jokes or quips, but through behavior and images. John Hughes seemed to like it, then he didn’t like it and fired most of the cast and Martha Coolidge, and we began again, going back to the simpler idea of Pretty in Pink with the sexes reversed.

MASTERSON: The character changed a great deal after I was hired. The character’s name was Keith, and it if was written today, you would say, “Oh this is a trans character.” She would probably change her pronoun the way it was written originally. Her name was Keith, she wore BVDs, she was very butch and was his friend almost as a guy, not as a tomboy…They said, “Well, why don’t we just pick a drummer and have a gender neutral name, like a last name or something.” I ended up being Watts for [The Rolling Stones’] Charlie Watts and Eric Stoltz’s character became Keith.

DEUTCH: When I came back, it was not the same script. It wasn’t as funny, and Eric Stoltz made more sense for the part because it wasn’t really as comedic a part.

STOLTZ: I thought the script has too much middle-class resentment in it – having Keith long to ‘take down’ the rich, white bully made him care about the system he was trapped in, and I thought it made it more interesting if he was an actual rebel who didn’t mind not ‘belonging.’ We went round and round about that for awhile, but in the end, it was John’s world that we were living in, so Keith became more an ‘everyman’ and less of an outcast. Interestingly, there are still moments of the darker fairy-tale within it.

MASTERSON: [Hughes] wrote the soundtrack before the script. The soundtrack didn’t change, but the screenplay did dramatically. He actually had the tone right in the soundtrack, and the screenplay didn’t really fit with what he was hearing in his head.

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Once Deutch came back on to the film, he only had a few weeks to find his leading lady, Amanda Jones — Keith’s dream girl — and cement a sense of what each of these characters would be.

STOLTZ: I remember Howie Deutch asking about Lea Thompson, knowing that I was friends with her and we thought she’d be great. So I hopped on my motorcycle and took her the script. She was living up on Mulholland Drive at the time.

DEUTCH: I saw Back to the Future, and I was a big fan. Who wasn’t?

THOMPSON: Howard the Duck came out, and it was a huge bomb. It was very maligned, and I thought my career was over. Howie came back on Some Kind of Wonderful, and he fired Kim Delaney, and my friend Eric Stoltz [rode] up to the top of Laurel Canyon and said, “Howard Deutch wants you to reconsider the part of Amanda Jones.” Four or five days later I was shooting.

DEUTCH: I was frankly lucky to be able to have her in the movie. She elevated the part, and between her and Mary Stuart, it was like a great dance they did together in the movie. The movie endured because people identified with both those characters so strongly.

THOMPSON: The way [John Hughes] rewrote it, the character had a lot of depth. I was an icon of pretty, girl-next-door, virginal sexiness, from doing the greatest part of all time for that, which was Back to the Future. Some of the stuff Amanda Jones says is stuff I was actually feeling, like “You just love the image of me. You don’t love who I am.” People don’t see who I am — they just see the image of me and project their thing on that, which is the truth about being a pretty, young girl. There’s a lot of expectations that are exhausting to try to live up to. I liked that I got to say some of the stuff I was feeling at the time in the movie.

MASTERSON: I’d just finished At Close Range, and my hair was very red in that movie, and my roots were growing out. I went in and auditioned, and Howie thought it was cool that I had this weird hair. It was really benign neglect, but then that became a big part of the look of the character – the two-toned hair, cut short and kind of messy.

STOLTZ: After shooting for a few weeks, production shut down so they could cut my hair and make me a “more attractive lead” – even though the role was written as an artistic loser, mocked by the popular kids.

Keith and Watts are both creatively-minded. Keith is a visual artist – his room is covered in his work and he dreams of going to art school. Watts is a drummer, and she is rarely seen without a pair of drumsticks in her hand, accentuated by her penchant for a pair of red fringed gloves.

MASTERSON: I got ready to be in Some Kind of Wonderful by learning how to play the drums. I was training with this amazing drummer named Billy Moore. I would go to his studio every day and do exercises and work with him. He was like my personal Yoda….She just plays the drums by herself in a room in a couple of scenes. There’s nothing all that special or unique, but it was a great thing to learn because I wanted to have it in my body.

STOLTZ: I did take painting lessons. I spent some time in that world and painted some things that may or may not have ended up in the film. I hope they didn’t because they weren’t very good!

MASTERSON: I argued with the fringe on the gloves because I was like, “This is so impractical to get wrapped around your drumsticks!” They like, “No, they’re really cool.” I still have them.

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To help Keith prepare for his date with Amanda, Watts suggests he practice kissing her. He agrees, but their kiss nearly becomes something more as she wraps her legs around him and his hands dip lower into her back pockets, which the camera fluidly tracks.

DEUTCH: That scene wasn’t in the script period. Then, John said to me, “You know we need one more scene.” I remember him saying, “Let’s call it the kiss that kills.” He wrote that scene literally in front it me in like a half hour or less.

STOLTZ: Mary Stuart and I [had] a terrific working relationship, and we were pals, which always helps when you have that kind of scene. It was also a very hot and sweaty day in Los Angeles.

DEUTCH: It’s always moving to me when people are falling love, where there’s that electrical moment that’s rare. It’s the way you touch each other, it’s not just the kiss. It’s everything; every part of your anatomy is alive, and so we just talked about showing all of that.

MASTERSON: It’s very cool because of how it was shot. I thought it was really smart. It’s no fun when you do a scene like that, and it’s shot in a way that doesn’t emphasize the dramatic material in the kiss.

DEUTCH: I had a great cinematographer named Jan Kiesser and we collaborated on it. We shot a master, and when we started to cover it, it [seemed] like why not be more lyrical about the show and let it flow? That’s how it feels like that. It’s not just editorial cuts; it’s more designed.

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As Keith prepares to go on his date, his father, Cliff (John Ashton), learns that his son has blown all of his college money on a pair of diamond stud earrings. The two argue, but ultimately Clifford supports his son.

THOMPSON: I thought it was a bizarre plot point to be honest. A very strange thing. That he would cash in his college [money] to buy these stupid diamond earrings.

STOLTZ: I thought it was nuts then, and I think it’s nuts now – nuts and terribly romantic.

JOHN ASHTON (Cliff Nelson): We did a lot of rehearsing off camera, Eric and I. The funny thing is he never called me John. He always called me Pop. The whole time we were shooting, even off camera. We’d go to lunch and he’d call me Pop. When we finished our last scene, we went and had lunch and he called me John.

STOLTZ: Ashton and I got along famously. We had to reshoot that scene a few months after we wrapped, and if you look closely, you’ll see my hair is a different color. I was doing another job that dyed my hair. So we wet it and gave me a towel as though I’d just got out of the shower to help hide [it].

ASHTON: In the original scene, I had mentioned that he bought the earrings for $10,000. When they screened it for an audience, [they] didn’t believe a working-class [guy] like that would spend $10,000 on earrings, so we had to reshoot the scene and not mention the amount.

For his date with Amanda, Keith recruits Watts to be his chauffeur as he takes her out for a night on the town in an old-fashioned car. After dinner, their first stop is to an after hours art museum, where he has hung a painting he made of Amanda on the wall.

DEUTCH: I saw [that car] on the road actually. I thought that’s what the car should look like, and they found it and made a deal with the owner.

MASTERSON: We did a lot of that as a process on the stage, but I [drove it] a little bit.

STOLTZ: [Being in a museum after hours] was lovely, like being in a church.

DEUTCH: I’m pretty certain it was LACMA [the Los Angeles County Museum of Art].

THOMPSON: Howie had a really big crush on me, and I was engaged to Dennis Quaid at the time. This painting was such a big reveal, and Howie just couldn’t get anybody to paint the painting right, so he had 12 paintings painted of me. They’re still lurking somewhere. They’re still in the Paramount warehouse somewhere.

DEUTCH: We still have one of [those paintings of Lea], and it’s still hanging in our house.

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Keith then takes Amanda to the Hollywood Bowl where the two sit on the stage for a heart-to-heart. He gives her the earrings and they kiss, while Watts looks on from the cheap seats.

THOMPSON: Every time I go to the Hollywood Bowl, I remember sitting there on that stage and how cool it was to be there.

DEUTCH: That was a difficult night, and it took all night. The Hollywood Bowl is enormous, and if you’re going to shoot it, you’ve got to shoot it wide, medium, tight, tighter. The idea was for Watts to have that feeling of being crushed emotionally, but from her point of view, seeing these two little specks on stage.

MASTERSON: It was amazing to be in that space alone. I loved that day. It’s similar to [rehearsing in an empty Broadway theater.]

THOMPSON: It’s a weird, big, lonely place. It was interesting idea to make this very, very small scene about these little diamond earrings and put it in this epic place.

DEUTCH: The next morning I was told the lab had scratched all the film. I was devastated because I was really happy with what we’d shot. We ending up using the original footage, not re-shooting it, and cutting around the scratches. That was a nightmare.

Keith decides to go and face down bully Hardy (Craig Sheffer) at his party and take the potential beating coming to him. Watts reluctantly drives them to the party. Keith’s friend from detention, Duncan (Elias Koteas), shows up with his tough guy friends to defend Keith, and Amanda gets the last laugh, giving Hardy the slap he deserves.

DEUTCH: We had a stunt coordinator, and Lea slaps him twice. That was Lea’s idea, and I loved it, so we kept it.

THOMPSON: Craig Sheffer made me really slap him. He’d be like, “Harder! Slap me harder!” and I’d be like, “No!”

STOLTZ: We all wanted to have more Elias Koteas in the film because he was beloved. In the original script, he had only a few lines and when we discovered how unique and talented he was, Howie Deutch kept expanding his role.

THOMPSON: In that scene, I just slapped [Hardy] and left. They added the gang coming in. [Elias Koteas] was such a revelation, and I remember being so transfixed with his performance. That’s why they did that reshoot with the party added him because he came off so well you really wanted to see him again…You can tell if you watch the movie that Eric Stoltz’s hair changes. He’s wearing a wig.

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By the end of the night, both Keith and Amanda have become fundamentally changed. It seems they might end up together as Watts tearfully storms off down the road alone. But Amanda realizes it’s Watts he really wants and takes off the earrings, sending him to chase her down the street. They kiss; he gives her the earrings and jokes, “You look good wearing my future.” After having to reshoot the final scene of Pretty in Pink, both Deutch and Hughes were relieved to get their preferred ending here where the two best friends end up together.

DEUTCH: It was in Hancock Park where we shooting, and they have this ironclad rule of being out of there by midnight.

MASTERSON: I just remember being cold, and there’s this huge crane, and they make this big deal about these earrings. I wasn’t sure. It’s a totally materialistic thing. This doesn’t really jive with this character. But she couldn’t admit that she really wanted them – I can deal with that.

STOLTZ: That was the last scene we shot in the picture, which was nice, knowing you’re saying goodbye to all the people you’ve become close to during the production, but also knowing it’s probably the last time you’ll see them for many years. That always heightens what’s going on in the scene.

THOMPSON: Howie thought he was gonna have to shoot [a different ending]. But he didn’t. He thought they’d want Keith to end up with me but they went crazy for [Watts].

DEUTCH: I know we shot a lot of takes on that because it was our ending, and it meant so much to me. When we finally got it, I cried and everybody cried. Sometimes you get lucky and the chemicals work between everybody and the shot works. I wanted it to be almost operatic. I’m very happy with that ending.

The film has gone on to endure as one of Hughes’ seminal teen romantic comedies of the 1980s. For Deutch and Thompson, it has an even deeper resonance, having brought them together.

THOMPSON: I love the movie because I met my husband, and I’ve been with him for a long time, and we have two kids, and it was a super important moment in my life.

DEUTCH: The relationship was professional on the movie. She was engaged to someone else. I adored her.

THOMPSON: Howie works really hard and cares so much about actors and their process, and that was something I hadn’t really experienced very much as an actor. That made me feel like he was special. I just loved how hard he worked on the movie, how important it was to him…Something about that was super attractive to me and endearing. When you watch someone have passion and be really good at their job, it’s very attractive.

ASHTON: It’s a universal story. You look at someone from afar and think that’s the one – and the one is really right next to you.

STOLTZ: It’s a lovely fable with a strong female presence, a bit of subtle gender bending, and an excellent soundtrack. John Hughes took his teenagers very seriously. It’s not exploitative or crass – he respected and loved them.

MASTERSON: Nobody had ever really done that. The stakes are so high when you’re in high school – it’s not dumbed down. It’s honest and emotional and gave respect to that whole time of life.

DEUTCH: John was a romantic. If you really look at his writing, he was in love with love.