If You Leave You'll Miss These 25 Secrets About Pretty in Pink

It's been 35 years since the John Hughes classic starring Molly Ringwald, Andrew McCarthy and Jon Cryer hit theaters. But did you know it almost starred Charlie Sheen and Robert Downey Jr.?

By Tierney Bricker Feb 28, 2021 12:00 PMTags
Pretty In PinkMoviestore/Shutterstock

 Justice for the Duckman!

We don't know if you're emotionally ready for this, but Feb. 28 marks the 35th anniversary of Pretty in Pink, the late John Hughes' seminal coming-of-age romantic drama. Starring the iconic filmmaker's then go-to leading lady Molly Ringwald, Andrew McCarthy and Jon Cryer, the Brat Pack teen flick was a Romeo and Juliet-esque story about Ringwald's Andie, a quirky girl "from the wrong side of the tracks," who ends up with a preppy guy named Blane (McCarthy), because yes, that's a name, not an appliance. 

Pretty in Pink delivered one of the '80s most epic love triangles, plus music and costumes that would go on to define the decade and a generation. But the making of the Howard Deutch-directed movie was anything but pretty. McCarthy and Cryer were far from being the first choice for their respective roles, two of the leads "hated" each other and the original ending earned literal boos from test audiences. 

Remembering John Hughes (1950-2009)

To properly celebrate its 35th anniversary, check out 25 behind-the-scenes facts you might not know about Pretty in Pink, including the iconic line that was ad-libbed by Cryer and how Ringwald really felt about that pink prom dress. Spoiler alert: It was anything but volcanic. 

1. John Hughes wrote the movie for his muse Molly Ringwald. But the star of teen hits The Breakfast Club and Sixteen Candles felt ready to move on from high school-set films to more adult roles and initially didn't want to sign on for Pretty in Pink.

"As far as the character, she's so much like I am," said Ringwald in a 1986 interview with MTV. "I had to do it because John wrote the script for me right after we did Sixteen Candles...If anyone else played that part it would be like somebody wearing my clothes, you know? I had to do it."

2. But her hesitance had already caused Hughes to move on, finding another actress to play Andie. "John was mad at me and didn't want me to do the movie," Ringwald revealed on Alec Baldwin's Here's The Thing podcast in 2016. "They were going to cast Jennifer Beals because she had just had a success with Flashdance."

3. Ultimately, it was director Howard Deutch who stepped in to diffuse the tension. "Howie was actually the one that said, 'But no, Molly has to be in this. This is for Molly,'' Ringwald shared.

4. Charlie Sheen was the actor Hughes had in mind for Blane, who was described as a square-jawed jock in the script. But, according to the Brat Pack memoir titled You Couldn't Ignore Me If You Tried, it was Ringwald who convinced the filmmaker to hire Andrew McCarthy.

"I did push for him to get hired," Ringwald revealed. "I was involved in all of the auditions, and I actually read with everyone, and I thought he was cute," she laughed. "And I thought, if I thought he was cute, then Andie would think he was cute! I liked that he wasn't typical, and he seemed so right for the part. Andrew McCarthy has always seemed so tortured with indecision, at least at the time, and so was Blane, who really is a tortured soul. And Andrew and his eyes. There's just nobody who has those tortured eyes."

5. McCarthy sent his leading lady an unusual thank you gift after Ringwald secured him for the role: A four-foot-tall Gumby doll. "I don't know why," McCarthy told You Couldn't Ignore Me If You Tried author Susannah Gora. "It was ridiculous."

6. Still, McCarthy wasn't exactly thrilled to be doing Pretty in Pink. "I needed the job, I wanted to go to work, and I was thrilled that anybody would give me another job," he told Gora, but once he read the script, McCarthy continued, he "wanted out."

7. Throughout filming, Ringwald and McCarthy were completely at odds, Deutch revealed. 

"They hated each other because Molly had a crush on him, and he did not have a crush on her," Deutch explained to Den of Geek. "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."

8. Originally, Hughes envisioned The Breakfast Club star Anthony Michael Hall as Duckie. But the actor passed, believing it was too similar to his previous role as the Geek in Sixteen Candles.

"It was shocking to John because John felt like he was his son," Deutch told Den of Geek. "He felt very close to him. You know, all those kids from Breakfast Club were like his family."

9. After Hall passed, Ringwald pushed for "somebody like Robert Downey Jr." because "he was different, and he was quirky, but it was completely imaginable that we would end up together," she explained in You Couldn't Ignore Me If You Tried. Michael J. Fox was also reportedly considered.

10. Of course, Jon Cryer would go on to make Duckie Dale an iconic character. "He walked in and he was my guy," Deutch told Gora.

11. But his co-stars didn't really like him, with Cryer explaining in his 2015 memoir, "I think they were irritated by me from day one. Molly and Andrew were very reserved people, and I'm a very outgoing person. That could have worked out great, that dynamic, but it didn't."

And he wasn't wrong, as McCarthy admitted to Gora, "Jon was very Duckie-like when we were making that movie. He was very sweet and very needy, and I had no patience for it."

12. Pretty in Pink originally ended with Andie choosing Duckie over Blane. But during test screenings, audience members actually booed. 

"These kids that they recruited to watch the movie were screaming, loving the movie, screaming. It was like a hit! And then all of a sudden, the minute the ending came and Duckie was gonna be the hero they started booing," Deutch recalled to Den of Geek. "And I said, 'I'm literally gonna have a heart attack'. The whole movie has been built for that. We were all thrown."

13. An omen that the original ending wasn't going to work? Ringwald was extremely sick, even fainting during a slow dance with Cryer. During their reunion photoshoot for Entertainment Weekly in 2011, Cryer joked, "Wow, it's been 25 years since she laid her head on my shoulder. Hopefully this time she won't end up projectile-vomiting."

14. To reshoot the final scene, McCarthy had to wear a wig after shaving his head for a Broadway play. 

"They threw a bad wig on me," he said on Access Hollywood Live in 2011. "If they knew we'd still be talking about it 25 years later, they would have paid for a better wig."

15. While Ringwald loved everything else she wore in the film, with costume designer Marilyn Vance interpreting a lot of the star's personal style into Andie, she penned a 2017 op-ed for Teen Vogue about the iconic pink prom dress, which she hated.

"If I'd had it my way, I would have burned the dress on the Paramount back lot as soon as they yelled the last 'Cut! Print!'" she wrote. "When I saw the dress for the first time, I burst into tears. The only thing I liked, and even vaguely remembered from the consultation, was the halter neckline. The puffy sleeves and inverted-triangle, sack-like silhouette confounded me, but it was too late to change it."

16. Vance designed the dress and used cut up pieces from various gowns  to create it. 

"I won't say that I was in love with it," Vance admitted to the Huffington Post, going on to add it wasn't mean to be a gown every girl would want. "But that's not the character. The character was so original. She had a mind of her own, she marched to a different drummer."

17. Cryer ad-libbed one of Duckie's most infamous lines: "He has a name, Blane? Blane sounds like a kitchen appliance, that's not a name." Speaking to Entertainment Weekly, Cryer explained, "That was me. John cast people that he liked, and then he tried to incorporate as much of what they could bring as he could [into the script]."

18. Ringwald recalled James Spader's memorable audition for yuppy bad boy Steff in a DVD feature, with Deutch also revealing Hughes had to convince him to hire the actor because he was that abhorrent during that first meeting. 

"I remember James Spader coming in and smoking a cigarette...and he was just obnoxious, but he was completely in character because he's actually...very nice and not at all like the character he plays," she said. "But he just had this real sneer about him and I think he even dropped the cigarette on the floor and stamped it out, and just left."

19. Oh, and the moment Steff spits on the ground in the school hallway after his fight with Duckie? Unscripted.

20. To prepare for Duckie's infamous dance scene, Cryer worked with choreographer Kenny Ortega (who would go on to direct High School Musical and Hocus Pocus).

21. After Cryer showed Deutch what he wanted to do for the performance, the actor recalled in an interview with EW, "they cleared the shop and I had performed it full out, and he didn't say anything afterwards." Deutch's blank stare was actually hiding his irritation, as Cryer said the director realized the scene would be so good that they were going to have to extend their shoot to fully capture it. "We lost a whole day in the schedule in the very first week."

22. While Duckie ended up dancing to Otis Redding's "Try a Little Tenderness," the song was initially going to be Mick Jagger and Michael Jackson's "State of Shock."

23. Duckie's signature pointy-toed white shoes were one-of-a-kind and found by Vance at the same store where she purchased Julia Roberts' iconic thigh-high Pretty Woman boots. And Cryer held onto the footwear for quite some time. 

"I had the Duckie shoes for the longest time and then in the mid-'90s, I lent them to Planet Hollywood, which decided that I wasn't lending them, I was giving them—despite documents to the contrary," Cryer told EW. "They're probably in the last remaining Planet Hollywood in, you know, Singapore or something. Isn't that ridiculous? The Duckie shoes should be mine!"

24. The movie got its name from the song of the same name by The Psychedelic Furs, one of Ringwald's favorite bands.

25. "If You Leave" became the breakout song of the movie, but it almost didn't even make the soundtrack. Orchestral Manoeuvres in the Dark's "Goddess of Love" was initially picked for the final scene, but when the ending changed, the band wrote "If You Leave" in less than 24 hours. It went on to become OMD's highest-charting single, reaching No. 4 on the Billboard Hot 100 chart in May 1986. 

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