The casting of the role was crucial because, in many ways, Duckie represented the heart of the film. He’s the unflappable dreamer who dares to love a girl who is definitely, to paraphrase the Tom Hanks/Jon Lovitz Saturday Night Live skit, outta his league. And depending on the actor tackling the role, this loving can be seen as pathetic, laughable—or as something else entirely, something laudable and brave. “I felt like if the movie was going to work, this character had to work,” says Deutch. At one point, says Ringwald, Hughes had Michael J. Fox in mind for the role, but Fox became unavailable because shooting on Back to the Future went longer than expected. Various actors, including Robert Downey, Jr., and Patrick Dempsey, were considered. And then there was Jon Cryer. “He walked in,” says Deutch, “and he was my guy.”
Cryer, who had made a name for himself as a teenager on the Broadway stage, starring in productions of Brighton Beach Memoirs and Torch Song Trilogy (stepping into both roles after his doppelganger Matthew Broderick had left them), had appeared in the film No Small Affair with Demi Moore. Jonathan Niven Cryer, a walking bundle of charming, self-effacing ebullience, was born on April 16, 1965, and raised in New York City. He went to high school at the intellectually rigorous Bronx Science, where he considered himself “part of the bohemian, but not particularly smart, crew,” Cryer says. He had admired Hughes’s sardonic writing in National Lampoon and was a great fan of his films. Such a fan of Hughes’s comedic style was Cryer that when he first read the script for Pretty in Pink, he says, “I was at first disappointed that it wasn’t a goofy comedy like Sixteen Candles, which really is a pretty goofy comedy, in retrospect. I mean, Long Duk Dong, for Chrissake!” But then he came to appreciate the deeper, more serious tone of Pink: “What I loved about it was that it was actually a drama. It took itself very seriously. When I read the part, I said, ‘I love this guy. He’s the guy I wish I could be.’” Cryer went in to read a scene for Deutch, who then asked him to read another, and another, and another, “until we read the entire script, in terms of Duckie,” Cryer recalls. Later his manager told him that the filmmakers wanted him to come back and read with Molly Ringwald.
In one scene in the script, it had been written that Duckie would enter Trax, the record store where Andie worked after school, and that when he walked in the door, he would be singing. Cryer saw this as a golden opportunity. “My friends had always said I did a great Mick Jagger impression,” he says sheepishly. “And Michael Jackson, of course, was huge at the time. So I came to the audition prepared to sing that song ‘State of Shock’ that Mick Jagger and Michael Jackson did together. I was going to do both of them, and combine them into one grand performance piece.” Cryer, who came to the audition sporting ridiculous Duckie-worthy sunglasses, remembers that when he read with Ringwald, “she was very remote. Not unfriendly, but just—you don’t know where you stand with her. So I come into a room and I’m like, ‘Hey! How ya doin!’ I’m talking a mile a minute. And she just sort of kept her own counsel—you know, like when people keep to themselves. So I was, of course, frightened by that.” Ringwald’s taciturnity worried him. “I thought, well, I blew this.”
After the audition, Cryer left the room, and as fate would have it, John Hughes was standing right outside the door. “I said, ‘Oh, hi. I’m a huge fan,’” Cryer remembers. “And he was sort of surprised that I read his stuff in National Lampoon. But he was very nice; he just wanted to have a conversation. He really wanted to go in depth, which surprised me, because it was an audition situation.” Hughes might have been having such a long conversation with Cryer as a sort of extension of the official audition the actor had given moments earlier, as a way to gauge Cryer’s personality further. “I was shocked at how attentive he was,” Cryer says. “He wanted to talk about what I thought of the character, and what I wanted to do with him.” Somehow it all clicked, and the filmmakers decided to cast Cryer in the role of Duckie. It was great news—but nobody bothered to tell Cryer. Finally, his manager called Lauren Shuler Donner, who said, as Cryer recalls, “Oh, God, yes, we want him—we were just casting other people.” The lapse would be perfect preparation for his role as an underdog, but no matter how the news was delivered, says Cryer, “I was thrilled.”
Knowing how essential it was that the Duckie character be just right, Deutch and Cryer settled in for some intense brainstorming sessions. “I had him move into my house, practically,” Deutch says. “I was with him twenty-four hours a day—I felt the responsibility of that character. I was taking a leap of faith in him.” Deutch also felt quite protective of his openhearted young star: “The main thing I remember thinking was, ‘You don’t want to hurt this kid. He’s very fragile—don’t hurt him.’” Of course, it was that very fragility, that optimism in the face of impending romantic doom, that made Duckie so cinematically resonant, and it took a Jon Cryer, whose off-screen persona embodied a Duckie-esque generosity of spirit, to make it work. The character’s unique essence was further defined by costume designer Marilyn Vance, who dressed Cryer in eccentric duds straight from the 1950s and a high, fluffy pompadour. “Marilyn put me in these insane outfits,” remembers Cryer, “and at first I thought, ‘Why does it have to be so goofy?’ And then I realized, of course, that’s Duckie’s ‘fuck you’ to the world.”
For Cryer, working on Pink was the actor’s “first time starring in a big, expensive movie. We had a huge crew, decent dressing rooms.” It was a big step up from his first movie, No Small Affair. For that shoot, Cryer says that his dressing room was “a slot in a honey wagon.” But there were some perks to that film, such as getting to do some intense on-screen making out with costar Demi Moore. Cryer contracted mononucleosis during the shoot, and when asked if he got it from Moore, he coyly replies, “Well, I’m not gonna say. I like to think that I’m discreet.”
James Spader rounded out the primary Pink cast. It was one of his first film roles. Born on February 7, 1960, in Boston, Spader, the son of two teachers, attended the exclusive Phillips Academy. At seventeen, he dropped out of school and moved to New York to try his hand at acting. “When I moved there,” he told the Boston Globe, “I completely believed that anything was possible. I believed I could become part of the fabric of the city, and not by portraying someone, but truly.” He worked many odd jobs, including a stint as a manure shoveler. Spader’s first screen credit was a small part in a low-budget comedy from 1978 called Team-Mates (aka Young Gangs of Wildwood High), and he then played Brooke Shields’s brother in 1981’s Endless Love, but gained more attention in 1983, with roles in a series of movies-of-the-week. In 1985, he was seen in a starring role in the B movie Tuff Turf, in which he played a Connecticut prep student who moves to L.A. and is roughed up by high-school bullies when the girlfriend of one of them falls for him. (The otherwise forgettable movie’s horrid musical numbers live on, thanks to YouTube.)
But Spader’s breakthrough would come with Pink, in which he would play McCarthy’s cruel best friend, Steff. Spader came to the audition completely in character—smoking a cigarette in the room where he read his lines for the filmmakers, and then dropping it and crushing it out on the floor on his way out. Spader, who is often said to be very kindhearted in real life, was so despicable in character during the audition process that Hughes and Deutch were put off by him, until they realized how perfectly he was capturing Steff’s arrogance. Spader was cast, and when Cryer first met him, he told him he’d admired his work in a bunch of TV movies in which he’d played a jerk. “Yeah,” Cryer remembered Spader saying to him, “I figure I got a lock on this teenage asshole thing.” Indeed, the part of Steff would launch him into an early career of playing skin-crawlingly vile preppies with a patrician manner. “I’ve played a lot of bad guys in my career,” Spader once said. “They are more interesting to me. They are there to propel the film, and I like that. I’ve never been comfortable with inaction.”
With the cast locked in, production could begin in Los Angeles.
In his earlier films, Hughes had learned the imp
ortance of letting his actors try out new things. And so on Pink, when an actor suggested something that added a worthy element to the script, Hughes and Deutch were happy to incorporate it into the story. Cryer, in particular, was a tremendously gifted comic, and when he came up with clever quips that worked within the context of the story, Deutch and Hughes would let him run with them. One of the movie’s most beloved and oft-quoted lines—in which Duckie, upon first hearing that Andie’s new boyfriend’s name is Blane, replies, “Blane? That’s not a name, that’s a major appliance!”—was something Cryer came up with himself. Similarly, Cryer drew upon one of his real-life teenage experiences when he devised the bit where Duckie riffs on an object in the girls’ bathroom. “The one time I was in the girls’ room in my junior high school,” Cryer remembers, “I saw this [tampon] machine on the wall, and I was like, ‘What is this? They have a candy machine? This is fantastic!’”
But without a doubt, Cryer’s most unforgettable scene in the film, the scene that he himself admits is—in his entire career—“certainly the most memorable thing I’ve done,” is the one in which Duckie serenades Andie and Iona with an over-the-top, exuberant, painfully passionate lip-synching/dancing performance of Otis Redding’s “Try a Little Tenderness.” “On Broadway they have the term ‘an actor who moves well,’” says Cryer. “I was one of those. It just means that I can do sort of basic steps, but I can really sell it.”
And did he ever sell it. Pounding his fist on the ground, gyrating his pelvis into the air, Duckie danced his way into a generation’s collective consciousness in that scene. After being told by Deutch that the Mick Jagger song that Cryer originally had in mind wouldn’t work, in large part because using it would be too expensive, Cryer was informed that the song would be the Otis Redding classic, and that he would be working with uber-choreographer Kenny Ortega (of Flashdance and Footloose fame, now the director of the High School Musical movies). “Howie got me together with Kenny,” remembers Cryer, “and in the course of an evening we figured out what we wanted to do. When I first performed it for Howie and Lauren, we were in the record store. I was really happy with it, and Kenny was really happy with it. We did the big finish and we look at Howie and Lauren expectantly, and they’re both not happy. And I thought, ‘What’s the matter?’” It wasn’t that Deutch and Donner didn’t like Cryer’s performance. Au contraire. Deutch said, as Cryer recalls, “‘The problem is, we have to shoot it.’” The filmmakers didn’t have the time or the money to film the sequence, and yet they knew, upon seeing Cryer’s unforgettable dance, that they simply had to. “The amount of time it would take to shoot such a big dance sequence would put [Deutch] behind schedule in the first week of a shoot,” says Cryer, “and he was a first-time director. That’s not where you want to be. Then you’re behind the eight ball for the rest of the movie. So he was looking at spending the rest of the movie arguing with the studio every day. But to his credit,” says Cryer of Deutch, “he took the risk.” (Months later, the power of the scene would dawn on Cryer: “It wasn’t until I actually saw it at the premiere that I realized the dance was going to be a big deal.”)
Moments after Duckie’s stunning song and dance number comes one of the film’s most painful scenes: Blane arrives at Trax to pick Andie up for their date, surprising Duckie, who then, for the first time in his life, reveals his feelings for Andie in a storm of jealousy, sadness, and rage. It is just one of many scenes in which Cryer’s dramatic style of intensely expressive, heart-on-your-sleeve acting, blended with Ringwald’s more quiet, natural tone in a peculiarly effective way. “One of the great things about Molly Ringwald as an actress was, it was very subtle,” says Cryer. “As an actor, I kind of put everything out there. But she holds a lot back, and it’s intriguing to watch.” Of the confrontation scene, in which Duckie tells Andie, “I would’ve died for you,” Cryer says, “I remember doing that scene and thinking, ‘Okay, when is she gonna start?’ Because everything she was doing was so small. But on film, it works great.”
Even though they played bitter rivals who get into a fistfight, offscreen, says Cryer, “I got along better with Spader than anybody else” in the cast. He certainly got along better with Spader than he did with McCarthy: “I don’t know if Andrew was just trying to keep a little distance,” says Cryer. “I don’t know if he just didn’t take a shine to me or what.” Indeed, there seems not to have been much affection between the two actors. “Jon was very Duckie-like when we were making that movie,” McCarthy has said. “He was very sweet, and very needy, and I had no patience for it.”
“There were a couple of incidents where it just sort of went wrong,” Cryer allows. One such incident was the filming of the scene in which Duckie and Iona are unexpectedly joined in a nightclub by Andie and Blane, who are on their first date. In a display of petulant childishness, Duckie ignores Andie, insults Blane, and French kisses Iona to make Andie jealous. Duckie hates Blane for sweeping in at the last minute and stealing the girl he’s loved forever.
The anger on Cryer’s face during that scene was particularly well defined. And for good reason: Cryer wasn’t entirely acting. During the nightclub scene, he says, McCarthy and Ringwald were ignoring him while he was filming his close-ups—not giving him anything to work with, in actor speak. Just as Duckie was pissed off in the scene, Cryer was pissed off as well, especially when he learned that Deutch had told McCarthy and Ringwald to purposely behave this way, to heighten the emotions of the scene. “I got all in Howie’s face,” says Cryer. “And Andrew actually came by later and apologized and he said, ‘Look, I didn’t mean to mess you up. Howie just thought [the scene] was just kind of laying there.’” Regardless, says Cryer, semi-seriously, “I still kind of never quite forgave [Andrew] for it.”
Over the course of shooting, the movie became infused with many elements of Ringwald’s offscreen persona. The actress was known for her proclivity for the color pink and for the Psychedelic Furs song “Pretty in Pink,” and Andie’s bedroom looked strikingly similar to Ringwald’s real-life bedroom, “but a lot neater,” says Ringwald, laughing. “There are actually some collages that I had made that ended up on the wall of my room in Pretty in Pink.” When Andie holds a framed black-and-white photo of her mother, the woman in the picture is actually Ringwald’s mother, Adele. The outspoken young Ringwald also imbued Andie Walsh’s on-screen outfits with her own personal, eclectic fashion style and penchant for thrift-shop finds. The funky vintage look Ringwald embraced was born out of necessity: she shopped in secondhand stores on L.A.’s Melrose Avenue because her parents kept her on an allowance. It was a perfect fit for the look of Andie Walsh, who had no choice but to use little money and lots of imagination to turn flea market clothes into fresh designs. In fact, of Ringwald’s iconic teen roles in the 1980s, she says that Andie Walsh “is probably the most like me…I liked that she was strong, and capable, and she just seemed like a good person, and a good friend.”
Duckie describes one of Andie’s outfits in Pretty in Pink as a “volcanic ensemble,” and indeed, the volcanic ensembles Ringwald wore on-screen and off made a real impact on youth fashion in America in the 1980s, and today. Her on-screen looks were unforgettable, from her chicly layered tops in Sixteen Candles to her lace-up brown leather Ralph Lauren boots in The Breakfast Club, her ingenious vintage finds in Pretty in Pink, and, of course, that prom dress she sews from hand-me-downs. “Ringwald’s style goosed fashion circles and high school social cliques alike,” wrote the Los Angeles Times’s Monica Corcoran. “She was an antidote to ’80s ‘power dressing’ and empowered the eccentric social underdog. Bypassing the mall for a musty Salvation Army became de rigueur and certified vintage as cool…Even today’s style mavericks—think Agyness Deyn and Chloë Sevigny—nod to Ringwald’s on-screen style as inspiration.”
There was a lot of John Hughes in Pretty in Pink as well. “Obviously this was such a labor of love for him,” says Cryer. “He may well have secretly had a thing for Molly. I don’t know. But clearly it w
as a really important project to him. Everything had this huge importance to him. He sweated the small stuff. He really took pains to make everything work. And because he was so invested, you couldn’t help but be.” On the set, Hughes and his beloved Ringwald were “very close,” McCarthy recalls, adding that their devotion to their work spread to the rest of their colleagues: “The lead came from her and John: ‘We take ourselves seriously.’” Cryer remembers that Hughes “listened to Molly in a different way than he listened to anybody else. Her opinion carried more weight than anybody else’s did.”
Though this was Deutch’s film, not surprisingly Hughes was intimately involved with the production. “Howie was hired by [Hughes] to direct the film, so there was that chain of command,” says editor Richard Marks, and Hughes was on the set nearly every day. This came in handy when rewrites were needed. “I’ll tell you one thing that shocked me,” remembers Shuler Donner. One day Hughes came in, and Shuler Donner started talking to him about making a few changes to the script. Normally, these kinds of changes can take days to make. But Hughes, remembers Shuler Donner, “walked outside to where my assistant was sitting at her typewriter. And he said to her, ‘Can you give me your seat for a second?’ And he just typed them out right there. And they were great.”
You Couldn't Ignore Me If You Tried: The Brat Pack, John Hughes, and Their Impact on a Generation Page 18