Some Kind of Wonderful, which re-teamed Pretty in Pink director Howard Deutch with John Hughes, wasn’t a hit at the box office (it grossed just over $18.5 million), and it’s often described as a gender reversal of Pretty in Pink. But non-Brat Packers Eric Stoltz, Mary Stuart Masterson, and Lea Thompson told a convincing story about a high school misfit named Keith Nelson (Stoltz) who manages to snag a date with Amanda Jones (Thompson), the most popular girl in school. Later on, he realizes he’s actually in love with Watts (Masterson), his tomboy percussionist best friend.

After writing and producing Some Kind of Wonderful, Hughes left the teen world behind and moved on to more adult fare with Planes, Trains and Automobiles and She’s Having a Baby. But Some Kind of Wonderful remains a touchstone in Hughes’ oeuvre and in the pantheon of adored teen movies. Here are 12 wonderful facts about the 1987 movie.

1. THE SCRIPT WAS ORIGINALLY CONCEIVED AS A SEX COMEDY.

“There was the first draft that was sort of like a broader sex comedy,” Mary Stuart Masterson told Entertainment Weekly, explaining that “my character was named Keith and she wanted to be male.” In Susannah Gora’s book, You Couldn’t Ignore Me if You Tried: The Brat Pack, John Hughes, and Their Impact on a Generation, Jon Cryer—who auditioned for the movie—remembered a subversive scene where Keith’s (then named Garth) watch gets stuck in his gym shorts in front of Amanda. “And he’s scratching his crotch. And the girl walks by. He tries to pull his hand out of his shorts, but his digital watch gets stuck on the inside seam of his shorts. So he’s struggling with it, which, of course, looks even worse.”

2. HUGHES WROTE FERRIS BUELLER'S DAY OFF WHEN HE WAS SUPPOSED TO BE REWRITING SOME KIND OF WONDERFUL.

Deutch and Hughes would work on the Some Kind of Wonderful script late at night, and Deutch would fall asleep on the couch in their office while Hughes typed up rewrites of the script. “He would stay up all night, music blasting, and at like 5:30 or 6 a.m., he’d hand me what was supposed to be a rewrite on Some Kind of Wonderful,” Deutch told Vulture. “We needed five pages, and it was 50 pages. I said, ‘What did you do?! What is this?’ and he said, ‘Oh, I didn’t do that. I did something else. Tell me what you think?’ And it was Ferris Bueller’s Day Off. He wrote the first half of the movie in, like, eight hours, and then finished it a couple days later.”

3. MOLLY RINGWALD AND ANDREW MCCARTHY TURNED DOWN ROLES.

Hughes offered his frequent collaborator Molly Ringwald a role in Some Kind of Wonderful, but she rejected it. “I declined because I felt like the script wasn’t strong enough and was too derivative of the other films I’d already made with John,” Ringwald told The Atlantic. “He wanted me to play the role of a character called Watts, which went to Mary Stuart Masterson, but I was ready to graduate from high school.”

McCarthy felt the same way. “Hughes asked me to do it. I had just made, like, three of those movies in a row,” he said in You Couldn’t Ignore Me If You Tried. “It seemed like we just kept making the same movie.” Deutch also offered a role to Michael J. Fox, who obviously passed.

4. LEA THOMPSON SAID “YES” TO THE MOVIE BECAUSE HOWARD THE DUCK BOMBED.

Lea Thompson was offered the part of Amanda Jones but turned it down because “I didn’t want to play second banana, and the Mary Stuart Masterson part was better. I was very jealous,” she said in You Couldn’t Ignore Me if You Tried. When Howard the Duck came out in 1986 and tanked at the box office, Thompson felt she needed to do damage control on her career. Deutch asked Stoltz if he knew Thompson, which he did (they’d worked on Back to the Future together before Stoltz got fired). Stoltz agreed to deliver the script to her house and she finally agreed to do it.

“I was so freaked out because Howard the Duck was such a brutal bloodbath,” said Thompson. “I was so afraid to even look the crew in the eyes. I cried the first day [of shooting]. I was like, I don’t know how to act. I just felt so vulnerable and beaten. In a way, it was like getting on a bicycle after you fall down.”

5. THOMPSON DIDN’T WANT AMANDA TO BE JUST ANOTHER “PRETTY GIRL.”

At first Amanda seems like her sole purpose is to break Keith’s heart, but Thompson pushed for Amanda to be more than that. “Her life is not perfect and actually you realize everybody has problems,” she told Brightest Young Things. “I was a really strong feminist as a young person and I always tried to break down the barriers of the female stereotypes in interesting ways, and I’ve always been really conscious of that even when I was creating Lorraine McFly in Back to the Future. I was really trying to find a deeper human underneath what could have just been one color.”

“I felt too many things were dependent on her physical beauty and I didn’t feel I was beautiful enough to carry that off,” Thompson stated in the film’s production notes. “Thus, I felt my character should have more inner beauty.” Deutch and Hughes listened to her and made Amanda “far more sympathetic.”

6. MARTHA COOLIDGE ENVISIONED A DARKER VERSION OF HIGH SCHOOL.

The film’s pre-production was fraught with drama, especially when Deutch left the project because of stress over not being able to find the right actor to play Keith. Valley Girl director Martha Coolidge stepped in and hired Eric Stoltz as Keith, Kim Delaney as Amanda, and Kyle MacLachlan as Hardy Jenns. (Masterson had already been hired.) “It was almost a silent film, because Martha had this interesting idea of trying to make it as much of a non-verbal, non-jokey teen film as possible,” Stoltz told Moviehole. “Clearly, the powers that be didn’t go for that.”

Hughes didn’t like the route Coolidge was taking the story in and asked Deutch to come back, which resulted in Coolidge’s removal from the project. Hughes transformed the film into a lighthearted comedy, without the darkness. This caused hostility between Deutch and Stoltz, especially because Stoltz liked Coolidge’s vision better. “That’s why I wanted to get involved, because the idea of making a darker version of Pretty in Pink that didn’t have the Duckies in it, was intriguing—sort of like making a darker version of a kid’s fairy tale,” Stoltz said in You Couldn’t Ignore Me If You Tried.

7. HUGHES SCREWED COOLIDGE OVER WHEN BROUGHT DEUTCH BACK.

When Hughes managed to talk Deutch into rejoining the movie, Coolidge was blindsided by her firing. Executive producer Michael Chinich had her come to his office to tell her the unfortunate news. “Michael was in tears when I got there and talked about his crushing disappointment in the film and his company,” Coolidge told Kickin’ It Old School. “He directed me to sit and told me what a great job I was doing. I thought maybe Eric had died and the movie was off. Then he said that they would be making the film but not with me. He said that I was fired, with no reason, and I had to leave the lot right away. I was in shock.”

Kim Delaney and Kyle MacLachlan were also fired immediately, but the studio wanted Stoltz to stay. “The experience was awful, a real artistic coitus-interruptus,” said Coolidge. “I hired a publicist to help me through the ‘Artistic Differences’ public story that the company and my agents had agreed upon.” Years later she ran into Hughes in an airport and he acted like “nothing had ever happened and he had never caused me such pain.”

8. THE MAIN CHARACTERS' NAMES CONTAIN REFERENCES TO THE ROLLING STONES AND THE WHO.

Watts was originally named “Drummer Girl” and didn’t have a formal name, but her nickname was “Keith,” named after The Who drummer Keith Moon. Masterson thought it was weird that her character had a man’s name, so she talked to Hughes and Deutch about changing it. “I gave all these notes, like, this character is written as a tomboy but I don’t think a tomboy is necessarily a woman that wants to be a man,” she said in You Couldn’t Ignore Me. “It’s somebody who’s just not willing to be a slave to the feminine manipulative paradigm … Why does she want a guy’s name?” So they changed her name to Watts, as in The Rolling Stones’ drummer Charlie Watts. Eric Stoltz became Keith, and Amanda was named Amanda Jones, after the Stones song “Miss Amanda Jones.”

9. KEITH HAD LONGER HAIR BUT THE STUDIO MADE HIM CUT IT.

With Coolidge at the helm, they filmed a few weeks with Keith having hair below his shoulders. “I was very greasy and odd looking. Because the guy was someone who wasn’t able to fit in, we thought that was a great way to go,” Stoltz told Moviehole. When Coolidge was fired, they shut down production. “Someone at Paramount came down and said, ‘We’re going to cut your hair, and clean up your act.’ I said, ‘But the role is a rebel who doesn’t fit in.’ They said, ‘You’re going to cut your hair, and we’ll clean you up.’ I said, ‘Oh, so this is how the world works.’” Stoltz also had to wear eyeliner and blush.

10. DEUTCH HAD SUCH A CRUSH ON THOMPSON THAT HE KEPT HAVING HER PICTURE PAINTED.

The director and actress met on the set, fell in love, and got married (they’re still happily married today), thought they didn’t start dating until after filming wrapped. In a pivotal scene during Keith and Amanda’s date, Keith takes her to a museum and reveals a painting he did of her. The truth is, the director was so smitten with Thompson that he commissioned about 10 paintings. “There were all these paintings and they were all lined up on the soundstage, and Howie kept saying, ‘No, it’s not good enough!’ They must’ve spent $40,000 on those paintings,” Thompson said in You Couldn’t Ignore Me If You Tried. Thompson kept two of the paintings. “I should have kept the other ones because people will tell me they’re touring the prop house at Paramount and they’re like, ‘I saw nine paintings of you at the prop house.’ I should have kept them all,” she told Brightest Young Things.

11. THE MOVIE'S ENDING IS MUCH DIFFERENT FROM THE SCRIPT'S ENDING.

In the final draft of the script, dated a month before filming began, Keith calls “Drummer Girl” by her real name, Susan, and tells her he loves her. In the movie we don’t find out her real name and the “I love you” part doesn’t occur. Both in the movie and the script, he gives her a pair of diamond earrings and says, “You look good wearing my future.” In the film, the credits start to roll, but in the script she says, “These babies go back in the morning. You’re going to art school.” He replies with, “We’ll keep one and make it a ring,” insinuating they should get married. Sensing his uncertainty, Drummer Girl says, “You don’t want to think about that one, do you?” They continue to banter for about a page more, about how that moment was her first kiss, and then Keith jokes she did it wrong.

12. THOMPSON THINKS AMANDA WOULD’VE BECOME A CEO.

When asked what she thinks Amanda would be doing today in an interview with Brightest Young Things, Thompson replied, “I think she would have been really successful. I think she would be an executive in the fashion industry. She had really cool clothes and hair. I think maybe she would have been some kind of boss, like in marketing or fashion, absolutely, definitely a CEO.”