Pretty in Pink may have been released in 1986, but its story of unrequited crushes and teenage angst still strikes a core with audiences nearly 40 years later.
Riding high off the success of The Breakfast Club the year before, writer-producer John Hughes reunited with teen icon Molly Ringwald for a melancholic romantic comedy that doesn’t take place entirely in Saturday detention. Orchestral Manoeuvres in the Dark’s “If You Leave” and the Psychedelic Furs’ title track perfectly scored that unforgettable teen malaise as Andie Walsh harbored a seemingly unrequited crush on her high school’s golden boy Blane. It’s no wonder Pretty in Pink was a hit at the box office, on the Billboard charts and with generations of teenagers dreaming of being in Andie’s position, but the drama wasn’t only happening on the big screen. Behind the scenes, the filming of Pretty in Pink was fraught with cast members falling out and a rumoured unrequited crush that mirrored the events of the movie.
In honor of Pretty in Pink‘s 39th anniversary on February 28, keep scrolling to find out about the movie’s original ending and more backstage drama:
Molly Ringwald
Pretty in Pink centers around Ringwald’s wrong-side-of-the-tracks character Andie Walsh being stuck in the quintessential high school love triangle, as she tries to choose between spoiled dreamboat Blane (Andrew McCarthy) and her quirky best friend Duckie (Jon Cryer). Everything builds up to Andie’s high school prom where she dawns a now-iconic triangular pink dress designed by Marilyn Vance, though Ringwald admitted in later years that she hated the gown.
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“[I’d want] pretty much anything but what I wore,” she told Good Morning America in 2024. “Anything would have been better. Marilyn Vance did the dress, the very ’80s sort of inverted triangle. It was not what I had imagined. I was not very happy with it and I really did want to change it, but now that I look back on it, it was very much of its time.”
Pretty in Pink originally screened for test audiences with a different ending where Andie chose Duckie over Blane at the prom, but a completely new scene was shot with Andie choosing Blane due to harsh early reactions. According to Paramount, footage of the scrapped Pretty in Pink ending has been lost to time.
“I definitely felt like the audience was going to have that reaction,” Ringwald told Vanity Fair in 2021. “It just didn’t make sense because of how the entire movie was structured and the way these characters were cast. I could maybe understand Andie choosing Duckie if Blane had been portrayed as a vapid punk or if there had been no chemistry between me and Andrew.
“But it didn’t make sense to have the entire movie be this Cinderella story [but] she doesn’t get to end up with the guy she wants. It would’ve been unsatisfying. Jon was fantastic in that role, but to me, in my mind, Duckie was clearly a gay boy with a fierce crush on his friend.”
A very passionate group of Pretty in Pink fans have long theorized that Duckie may have been coming to terms with his sexuality throughout the movie. Ringwald seemingly lent credence to the theory by telling Out Magazine that “Duckie doesn’t know he’s gay” yet in the film, though Cryer had a different interpretation.
“[Molly] said that the guy whom Duckie was based on was gay. It’s a different thing. Let’s be clear here,” the actor responded in a 2012 interview with Zap2it. “No, she actually said that if one projected beyond the movie, that Duckie would be out by now. And I respectfully disagree.”
Ringwald has been outspoken in calling out many of her 1980s teen comedies for being “homophobic” and “very white,” though she has also tried to put Pretty in Pink, Sixteen Candles and The Breakfast Club in context for the time in which they were made.
“Everyone says and I do believe [it’s] true, that times were different and what was acceptable then is definitely not acceptable now and nor should it have been then, but that’s sort of the way that it was,” she told NPR in 2018. “I feel very differently about the movies now, and it’s a difficult position for me to be in because there’s a lot that I like about them.”
“And of course I don’t want to appear ungrateful to John Hughes but I do oppose a lot of what is in those movies,” she added.
Jon Cryer
Cryer told CBS Sunday Morning in 2015 that he never felt comfortable around his Pretty in Pink costars. In fact, Cryer likened his character Duckie to “the guy [he] always wanted to be in high school.”
“Molly and Andrew were very reserved people and I’m a very outgoing person,” he pointed out. “That could have worked out great, that dynamic, but it didn’t. I think they were irritated by me from day one.”
Part of the off-screen tension was due to Ringwald originally campaigning for her friend (and future Pick-up Artist costar) Robert Downey Jr. to play Duckie.
“I had wanted Robert for the role. I think John [Hughes] wanted either Anthony [Michael Hall] or Michael J. Fox, who was gonna do it at one point but had to drop out because he got Back to the Future,” she confirmed to Vanity Fair. “It would’ve made for a completely different movie had any of them played Duckie. But once Jon [Cryer] stepped into that role, there was no question that he was the guy. He put so much of himself into that role that it’s impossible to imagine anybody else.”
Cryer and McCarthy hashed out their differences in a very public way following a 2024 screening of the latter’s documentary Brats.
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“When we made Pretty in Pink, we didn’t get along because he was a d—,” Cryer complained during a roundtable discussion, with McCarthy agreeing: “That’s very true.”
Cryer clarified on X that he was not “talking out of school” since he’d reconciled with McCarthy long ago, adding: “For the record, the man is a prince. We were just too young to understand each other.”
Andrew McCarthy
Cryer may not have been the only one feeling tension on the Pretty in Pink set. Director Howard Deutch claimed in a 2020 interview with Den of Geek that Ringwald’s very real, unrequited crush on McCarthy made for an intense filming experience.
“They hated each other. They hated each other because Molly had a crush on him and he did not have a crush on her,” the filmmaker claimed. “And then he resented that she was the foundation of it, and then it escalated. I had to lie to them. I had to lie to Molly and say, ‘Oh, no, he really does have a crush on you but he’s a guy so he’s afraid to show you.’ I had to play that in order to get this. Luckily for me, it added to the sexual tension. It helped the whole sense of ‘are these guys really gonna get together or not?’ I don’t think they were that conscious of what I was doing, but I think they knew it was working. That relationship was filled with conflict. You can’t manufacture that.”
Ringwald seemed to laugh off Deutch’s version of events in a 2021 interview with Vanity Fair, where she said she had no clue “what Howie is talking about.”
“I was only 17, and Andrew was already in his 20s, so we were definitely living very different lives,” she clarified. “But we got along fine and ended up doing another movie together a few years later. I feel like we had an interesting dynamic because we definitely were not a couple, and we weren’t really friends either, but we had a lot of chemistry.”
For his part, McCarthy told Entertainment Tonight that Ringwald fought for him to be cast as Blane since the filmmakers were initially looking for a completely different type of actor.
“That part was written for a square-jawed, big, hunky, you know, quarterback and Molly got me that part,” McCarthy said. “I auditioned and Molly said, ‘Oh, that’s who I would fall for. He’s dreamy. He’s poetic.’ And so John Hughes went, ‘Really? That wimp?’ … [Hughes] listened to Molly.”
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He credited the success of Pretty in Pink and Hughes’ other ’80s romantic comedies to the producer taking “young people and their emotional life seriously.”
“That’s why people [are] still watching those movies,” McCarthy added.
McCarthy reflected on his star-making performance and the heyday of the Brat Pack in his 2024 documentary Brats. He told Us Weekly at the time of Brats‘ release that he was disappointed Ringwald turned down his invitation to be interviewed.
“She’s so articulate and insightful about these things,” he told Us. “The Brat Pack’s a funny thing. It’s like an octopus — it has these long tentacles you still reach out and you can either feel them as an embrace or as something [else]. People are at different places in their lives”
Harry Dean Stanton
While the love triangle is the heart of Pretty in Pink, the emotional core of the movie revolves around Andie’s dysfunctional relationship with her hard-nosed father Jack (Stanton).
The elusive Stanton made his feelings about Pretty in Pink crystal clear during an appearance on the “Doug Loves Movies” podcast in 2013. Guest Jen Kirkman teed up Stanton for a huge laugh from the studio audience when asked if Andie was right to choose Blane over Duckie.
“I don’t give a f—, man,” Stanton replied.
Pretty in Pink is streaming now on Paramount+.
