My childhood fantasy went like this: Standing in a church doorway in a “Miss Pretty Princess” bridesmaid dress with a floral wreath in my hair, and bangs, which in retrospect have too much hairspray, I look up. “If You Were Here” shimmers in and a man who is criminally older than me appears, leaning against the door of a cherry red Porsche. Seeing him now, 25 years later, he looks a lot shorter than I remember, but back then, at age 10, I was a lot shorter, too. He’s still beautiful though, in a pair of perfect jeans, brown boots, a Fair Isle sweater vest as he coyly waves, as though any heterosexual woman on the planet, even one who isn’t one yet, would be happy to find him there. Just to be sure, I point at myself with my bouquet and mouth, “Me?” And he, his hair moussed up in front like the red fringe on top of a Roman helmet, whispers goofily, “Yeah, you.”

And that’s where it ends. There is no kiss over a cake because at 10 there were no kisses, just the dream come true: Sixteen Candles’s Samantha Baker finally landing her senior crush, Jake Ryan. “That’s like the perfect guy,” writer Jason Diamond says. “Except he makes rape jokes.”

Diamond’s forthcoming memoir, Searching for John Hughes, details his life growing up in the northern suburbs of Chicago, Illinois, where John Hughes’s teen canon took place. For Diamond (who’s also a Hazlitt contributor), and for me, Hughes’s films weren’t just aspirational fluff, they were aspiration leavened by reality. His heroes weren’t sun-smacked cover girls or matinee idols (well, besides Michael Shoeffling), they were kids like us—relatable role models. “They helped us figure out what to look for in our love lives, our friendships, our careers,” Susannah Gora wrote in You Couldn’t Ignore Me If You Tried; this applied particularly to the generation that grew up on them, particularly the girls. “It made girls of all makes and models feel like they could make a difference,” says Michelle Manning, producer on Sixteen Candles and The Breakfast Club. “It could not have happened if [Hughes] didn’t have Molly.”

Molly Ringwald, a pouty freckled redhead, was Hughes’s muse, starring in three of his four female-centric hormone-coms—Sixteen Candles, The Breakfast Club and Pretty in Pink. Hughes believed “girls tend to have a more considered view of life” and with the help of Ringwald, and other actresses such as Ally Sheedy and Mary Stuart Masterson, he created stronger, more complex female characters in an era that negated them. “He obviously loved women and saw his female characters as more than mere cyphers, there to make boys look good,” says Hadley Freeman, author of Life Moves Pretty Fast: The Lessons We Learned From Eighties Movies (And Why We Don’t Learn Them From Movies Any More). They proved that feminism wasn’t dead even though America kept insisting that it was.

John Hughes may have loved women, but the happy endings he gave them reflected the limitations of his own conservatism and that of the time. “As the 1980s body politic sought to rein in the female body that had been unleashed by the sexual revolution of the 1960s and 1970s, so too did John Hughes re-inscribe that domestic ideal of remaining within the ruling confines of the family, of continuing to be Daddy’s girl,” Ann DeVaney wrote in the essay collection Sugar, Spice, and Everything Nice: Cinemas of Girlhood. “In safe bedrooms, kitchens, school hallways, homerooms, and libraries, his girls act up and act out their adolescence, taking care of Daddy, wearing pink, not showing much skin, attending dances in school gyms, and being no threat to the patriarchal status quo of family or school. Hughes’s girls perform white, neoconservative teen sex roles and offer a powerful invitation to girl viewers to do likewise.” His characters were a contradiction, their non-conformity, their main attraction, ultimately subverted by a yearning to assimilate to the conventions of a decade defined by the mantra, “Greed is good.” And for those of us who were weaned on his films, it was virtually impossible not to be indoctrinated. “There were so many things in [Sixteen Candles] that were horrifyingly and politically incorrect,” says Haviland Morris, one of the stars of the film. “I think John Hughes got away with so much of it because the heart in his movies was so huge.” Thirty years on, however, we’ve dropped the rose-coloured glasses, and our response to realizing he sold us out to suburbia echoes Molly Ringwald’s response in Vanity Fair when he dropped her once she grew out of it. “It was very hurtful and it still hurts.”

*

John Hughes grew up surrounded by women and money. As a teen in the ‘60s, he and his three sisters moved with their parents to a wealthy suburb of Chicago where the variation in lunch money was divisive. “I always thought that was sort of tragic, and I still do, that for certain people things over which they have no control affect their lives,” Hughes said. In an essay for Zoetrope: All Story, he confessed that the “dark side” of his “middle-class middle-American suburban life” was nothing more than disappointment. “It bothers me if even one person comes out of that theater and says ‘John Hughes is a jerk because I paid $7.50 and look what I got,’” he told The New York Times in 1991. As a teenager he was a disappointment not only because he wasn’t as rich as the trust funders, but because he was an arty kid in a jock school. Feeling like the perpetual outsider, his first success was marrying the school’s ultimate insider, blond cheerleader Nancy Ludwig. His second success was building a family with her, and his third was supporting them by becoming an ad man. “It was the only way I could keep my wife and kids in food and heat,” he told the Chicago Tribune, “while still being somewhat of a writer.” “Somewhat” was an understatement: Hughes was famous for his prolific output, juggling marathon sessions writing humour for the National Lampoon magazine and, later, screenplays, with his day job and dad duties.

Early on Hughes became a fan of Frank Capra, the Republican filmmaker who embodied the American Dream. “He had this Rockwellian version of America,” Diamond says of Hughes, “but kind of also with the whole baby boomer, a little rebellion is fine, it’s natural, kind of thing.” No wonder he supported Barry Goldwater, the Republican Party’s nominee for president in 1964, who was economically conservative, but socially liberal. “From kind of a more left leaning mentality for a Republican, people gravitated towards him and got indoctrinated into the Republican party,” Diamond explains. “I think a lot of people who were free thinkers or artists or whatever got into him and their politics evolved according to how that party went.” Michael Weiss memorably called out Hughes’s conservativism in 2006 in a Slate piece titled “Some Kind of Republican.” “Hughes’ own coming-of-age was characterized not by the egalitarian zeitgeist of the ’60s but by a funk of jealousy for what the Joneses had and the Hugheses did not,” he wrote. “The polite term for this gentle rightward shift when it happens to artists and intellectuals is embourgeoisement.”

Hughes bought into the lacquered lie of the wonderful life.

On the 30th anniversary of The Breakfast Club, Hughes’s former National Lampoon editor, P.J. O’Rourke, referred to Weiss’s piece in a Daily Beast article about his friend’s politics. He explained that the two of them opposed the belief that “America itself was a flop and that America’s suburbs were a living hell” and considered the family “the fundamental building block of society” (which is why so many of the kids in Hughes’s films blamed their problems on their parents—Hughes did). There was a reason none of Hughes’s teens were real rebels, but rather outsiders with an eye on upward mobility. “The total abolition of authority and institutions would be a tragedy,” O’Rourke wrote. “If you get rid of all authority and institutions, worse authority and institutions arise in their place.”

Hughes bought into the lacquered lie of the wonderful life, that no matter your circumstances, the system allows you to succeed if you put in the work. And success is not so much independence as it is wealth and power. The heroines in both Sixteen Candles and Pretty in Pink end up with boyfriends who are richer, more popular and supposedly better looking than them. And by conforming to conventional beauty standards, The Breakfast Club’s outcast ups her social cachet with a popular athlete (while the older kook in Pretty in Pink bags a rich husband). As Weiss wrote, “[Hughes’s] portrayals of down-and-out youth rebellion had more to do with celebrating the moral victory of the underdog than with championing the underprivileged.” In an interview with the Times in 2004, Ringwald defended this contradiction—underdog embracing top dog—contending that the films were “Cinderella stories, and if Cinderella doesn’t get Prince Charming in the end, it’s a bit of a bummer, don’t you think?” Except that Hughes did not present his heroines as fairy princesses, he presented them as everywomen. And the moral of the story seemed to be that every woman, no matter who she is, no matter how unconventional she may be, wants to end up with Jake Ryan.

*

“He was fascinated by female adolescence and insecurity and how that manifested in behavior towards boys,” Sloane Tanen, daughter of Hughes’s producer Ned Tanen, told the Independent in 2011. For two and a half years, Hughes, who had no daughters of his own, called Sloane for tips and, at 13, she became the test audience for Sixteen Candles. Perhaps to thank her, the filmmaker later used Sloane’s name for the title character’s girlfriend in Ferris Bueller’s Day Off. “He really wanted to know what I was into and what I liked, who I was dating and how it was going,” she said. Then there was his pen pal, Alison Byrne Fields, who, following his death, published a blog in which she revealed Hughes once told her she had received more letters from him than “any living relative of mine has received to date”— according to The Washington Post, Fields exchanged about 20 letters with him between 1985, when she was 15, and 1987. Hughes told her he often used the argument “I’m doing this for Alison” to justify his decisions to Hollywood. But his number one girl would always be Molly Ringwald.

“When you hear a lot of people talk about how John Hughes respected teens,” Diamond says, “I think it really stems a lot from Molly first.” Legend has it that Hughes’s work at the National Lampoon—which attracted Hollywood attention—got him into the International Creative Management talent agency where, in pre-production on The Breakfast Club, he received a stack of headshots of their clients, including Molly Ringwald. “From what I heard from him, he put my headshot on the bulletin board by his desk and wrote Sixteen Candles over a weekend,” the actress told VF. “And when it came time to cast it, he said, ‘I want to meet her: that girl.’” But Hildy Gottlieb, Ringwald’s agent at the time, remembers it differently. Her boss, Jeff Berg, represented Hughes and asked Gottlieb to help his client cast his films. “I met with John, he gave me a shopping bag full of scripts,” she says. Gottlieb ended up reading two: Sixteen Candles and The Breakfast Club. “I said to John, ‘This young girl [Ringwald] would be great in these, why don’t you sit down with her? So he did.”

Hughes liked Ringwald immediately. “She was a real kid and she had a sense of that,” he told the Fort Lauderdale Sun Sentinel in 1986. “She hadn’t grown beyond her years.” Pretty in Pink producer Lauren Shuler Donner thinks he also liked how unique Ringwald was. “She was very much her own person,” she says. “She wasn’t like the other actresses in Hollywood—she didn’t look like them and she didn’t act like them.” Marilyn Vance, the costume designer on all of Hughes’s teen films except Sixteen Candles, concurs. “She wasn’t your average pretty young girl,” she says, and her maturity wasn’t average either. “She was more sophisticated for so young. She had an attitude.” That Ringwald wasn’t the “perfect, perfect beauty” was a particular boon, according to producer Michelle Manning. “There really weren’t a set of films that kids felt really spoke to them not at them,” she says. “I think with her specifically, there was a quality about her that he felt girls could relate to.”

“The kiss is the most beautiful moment.”

Ringwald’s hair wasn’t blond—she dyed it after seeing Anita Morris’s “mass of fiery red” on Broadway in 1982—nor was it long. “I had realized the futility of trying to look like what passed for beautiful in Southern California in the early eighties,” she wrote in her 2010 memoir-cum-lifestyle guide, Getting the Pretty Back. A portrait Ringwald recently tweeted from the ninth grade, pre-Sixteen Candles, shows a kid who skirted the decade’s “High Femininity” with a mix of pink and black—pink pearls, pink glove, pink sash, black boots, black shirt—Madonna crossed with Michael Jackson. “I dressed from my imagination,” she wrote, “sometimes in my excitement, I couldn’t just choose one thing—so I layered.”

Ringwald started acting on stage at age five and a year later she had appeared on a jazz album with her father’s band. After a brief stint on television—Diff’rent Strokes, Facts of Life—her first film came along in 1982, Paul Mazursky’s The Tempest, for which she was nominated for a Golden Globe. Being a professional at 13 seemed natural to her. She had grown up with a stay-at-home mom who felt “obsolete” and encouraged her kids to do differently. “It was always the idea that you will take care of yourself. You will never need a man to take care of you.” Ringwald told The Los Angeles Times. “It was drummed into my head.”

*

A teenager is invisible to both her family, who forgot her birthday, and the boy she’s in love with. It could be the plot of any number of B-movies that made up the post-Porky’s youth flick boom of ‘80s America. “What makes Sixteen Candles different is that this film looks at teenage love in an entirely new way—from the girl’s point of view, which is untouched territory as far as Hollywood is concerned,” Hughes told the Chicago Tribune in 1983. It was a surprising boast considering Sixteen Candles came two years after Amy Heckerling’s Fast Times at Ridgemont High, which circled the sex life of a female sophomore played by Jennifer Jason Leigh, and a year after the Martha Coolidge-directed Valley Girl starring Deborah Foreman as the eponymous adolescent. Perhaps Hughes meant he was the first male Hollywood filmmaker to touch the teen girl experience.

Samantha Baker (Ringwald) wants a “platinum” birthday with a “pink guy” (not a black one) , a Trans-am and STD-free sex on a cloud. Jake Ryan, the pink guy in question, drops his white-hot girlfriend Caroline Mulford (Haviland Morris) after noticing Sam looking at him like she’s “in love” and finding a note in which she names him as the person she’d “do it with.” He wants “more than a party,” even though Caroline’s fantasy—“I’m your wife, and we’re the richest, most popular adults in town”— isn’t that different from Sam’s. Jake wants to love a girl who will love him back, but it’s unclear whether Sam is in the position to do that (her summary of him: “Jake is this senior and he’s beautiful and perfect and I like him a real lot.”) She’s less conventional than Caroline, yet she wants a guy who is conventionally superior—older, richer, “hotter,” more popular. Caroline is equally hot, rich (presumably, though we know less about her than Jake) and popular, but she is “careless.” She does not deserve Jake, Sam does. “You know when you’re given things kind of easily, you don’t always appreciate them,” Sam’s dad tells her. “With you, I’m not worried.”

Sixteen Candles did not age well. First, there’s the entitlement of the hormone-infused Geek (aka Farmer Ted), played by a pubescent Anthony Michael Hall with a comically oversized head and bulging eyes. His voice barely cracked, the “king of the dipshits” behaves towards Sam every way you would hope a man wouldn’t—he invades her personal space and literally won’t take no for an answer. “Come on! What’s the problem here!” he squeaks. “I’m a boy, you’re a girl, is there anything wrong with me trying to put together some kind of a relationship between us?” In one scene Sam laughs at his admission that he “never bagged a babe” before he proceeds to roughly climb on top of her, recalling Margaret Atwood’s, “Men are afraid that women will laugh at them. Women are afraid that men will kill them.” But, the Cool Girl still gives him her undies to help him lie about having sex with her. “I mean, not many girls in contemporary American society today would give their underwear to help a geek like me,” Ted praises her.

Jake Ryan isn’t much better. More than 10 years after The Washington Post’s Hank Stuever wrote about the women who continue to pine for “Jake as the eternal belief in something better,” the New York Post’s Sara Stewart brought them back to reality. “In 2015, this movie plays out like Date Rape 101,” she wrote, “and both of its male leads, supposedly the heroes, are actually terrible, terrible people.” She referred in particular to the scene in which the Geek has an intimate conversation with Jake after his house party. “I can get a piece of ass anytime I want,” Jake boasts. “Shit, I’ve got Caroline in the bedroom right now, passed out cold. I could violate her ten different ways if I wanted to.” Instead of surreptitiously dialing 911, the Geek responds, “What are you waiting for?” Him, it turns out. Jake sends Caroline off in a car with Farmer Ted even though he’s underage—he can neither drive nor drink legally, though he does both—and literally goes gaga over her silk undies.

Producer Michelle Manning attributes the fact that these scenes weren’t flagged at the time to the era. “There was no PC, those things which are part of the culture of making movies today really didn’t exist,” she explains. “You didn’t think about it. There was no conversation about it.”

Havilland Morris told me she wasn’t aware of the recent online conversations about her character’s treatment by the men around her. In the film, Caroline is branded a loose woman. Of her birth control, for instance, she says, “It makes it okay to be really super careless!” This is Hughes’s take on women’s—Caroline is 18—sexual independence. Pubescent boy virgins, on the other hand, face no barriers to their libidos and are in fact expected to be “in perpetual heat.” It is jarring to see Morris, a fully grown woman, give Hall his first on screen kiss—“He was 15, I was 23,” she says. “It was a little odd.” —particularly after it is established that his character might have sexually assaulted hers, but Hughes seemed to be buying into the anachronism that it is the man’s job, no matter his age, to sexualize women; it is the woman’s job to protect her virtue. Sixteen Candles is intent on preserving the virginity of its female characters, throwing Caroline from Jake’s bed into the Geek’s arms, and saving Samantha for a mere kiss from the man who rescues her undies. Hughes leaves teen girls with an updated version of their childhood fairy tales, in which sex is not only “gratuitous” but non-existent. As he put it, “The kiss is the most beautiful moment.”

In this way, Hughes proffered a rare alternative to the subgenre of teen movies most prominent in the early ’80s, the sex comedy, which was erected around the success of raunchy films such as Porky’s. “I remember [Ringwald and Hall] always telling me to take out such and such a scene, usually a sex scene, because it was too gross,” he told the Chicago Tribune. He sympathised, telling Ringwald in Seventeen that, as a teen himself, he was “obsessed with romance,” rather than sex. “I think that’s an essential difference in my pictures,” he said. “I think they are more accurate in portraying young people as romantic—as wanting a relationship, an understanding with a member of the opposite sex more than just physical sex.” Well, the heroines anyway.

*

John Hughes’s most beloved film is about five high school archetypes—the princess, the basket case, the brain, the criminal, the athlete—who meet for Saturday morning detention and slowly strip away their tropes to reveal that they have more in common than they don’t. Costume designer Marilyn Vance, who was introduced to Hughes by Weird Science producer Joel Silver, layered the characters in clothes they would take off over time as a metaphor for the film’s theme. “I had to undo them,” she says. But they had some trouble with the buttons.

Hughes’s attempt to divest The Breakfast Club’s characters of their stereotypes did not extend to gender. The men were clothed in masculine-coded tropes while the women were left with the princess and the basket case, a vague redesign of the vintage hysteric. The latter, in particular, could be construed as the more revolutionary female take on the criminal, except that she is shackled by her sex. “What the male characters label lunacy in these films usually turns out to be a form of feminist resistance,” wrote Faludi. John Bender (the criminal) is allowed to be rebellious—is actually considered sexy because of it—but Allison Reynolds (the basket case) is not. In the latter role, Ally Sheedy spends the first half hour of the film mute, a girl trying to be invisible and succeeding. She wears heavy eyeliner to obscure her eyes, white foundation to cover her face and her hair shaggy to shield herself further. According to Sheedy, there was talk of cutting her hair to make it more punk, but she refused. “I was positive Allison should have hair she could hide behind,” she said in You Couldn’t Ignore Me (she would know— that’s what she did as a teen). Allison also dresses entirely in dark shades—she is a human eclipse in a time when, according to Vance, “black was not happening.” “The only other person who looked like that then was the Pretenders’ Chrissie Hynde,” Sheedy said in John Hughes: A Life in Film, “that pale, dark, androgynous rock-singer look.” While Allison’s mutiny ends up alienating her peers, Bender’s attracts them, his defiance ultimately excused after he discloses his abusive background. Being unloved at home earns him love (by Ringwald’s princess, Claire) at school, which redeems him in the eyes of ‘80s America.

Allison’s redemption does not come so easily. Though her family is also abusive, it is in a less socially acknowledged way (they ignore her). Being unseen at home does not automatically earn her the right to be seen at school—to be absolved she must turn herself into someone worth seeing. In the ‘70s, an era that liberated women from traditional gender norms, Allison would have been praised for her anti-conformity, but the ‘80s had no place for punks, only princesses. As The Breakfast Club progresses, she and Andrew Clark (the athlete, played by Emilio Estevez) form a connection but she is only allowed to kiss him after undergoing a makeover at the hands of the popular girl. “The ’80s backlash cinema embraces the Pygmalion tradition,” wrote Faludi, “men redefining women, men reclaiming women as their possessions and property.” Hadley Freeman “struggled” with the scene, in which Allison is unveiled in a pale ruffled camisole and Madonna hair bow, to the extent that she largely excluded the film from her book about eighties cinema. “I am not very into makeovers in movies as they always essentially teach women to be less of themselves to attract men,” she says. Indeed, the film suggests that to become Andrew’s property, so to speak, Allison must embrace the traditional sex roles he embodies, despite the fact that they cause him pain. Vance disagrees. “It was basically getting to the core of who she was,” she says. And Sheedy, who was raised by a feminist, did request that the makeover take off more than it put on. “John did give me that and they didn’t really put a whole bunch of makeup on me,” she told Elle, “it was more about revealing who Allison is.”

That was not the only scene Sheedy objected to. The Breakfast Club originally included a subplot in which a female gym instructor appeared topless, but it was scrapped when Ringwald and Sheedy protested. “It was like this little feminist uprising with Molly and Ally,” says Manning. “It was adorable, actually.” Hughes likely thought it was adorable too. He was famously collaborative, sitting with his young cast on the floor, picking and mixing from various drafts of his script. Judd Nelson, for instance, recycled the following exchange between his character and Ringwald’s:

Bender: Have you ever kissed a boy on the mouth? Have you ever been felt up? Over the bra, under the blouse, shoes off…hoping to God your parents don’t walk in?

Claire: Do you want me to puke?

Bender: Over the panties, no bra, blouse unbuttoned, Calvins in a ball on the front seat past eleven on a school night?

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Like Allison, Claire is essentially fodder for the male gaze. She is a “pristine girl,” sitting politely still as the men take turns harassing and defending her. She says one guy-one girl is “the way it should be” while Bender brandishes a parade of photos of women, to which he clearly wants to add Claire. “Let’s get the prom queen impregnated,” he says, before referring to her as “cherry” and asking Andrew, “Do you slip her the hot beef injection?” Claire’s final response is to give her harasser what he wants, a diamond and a kiss. “Why did you do that?” Bender asks in shock after she smooches his neck. “Because I knew you wouldn’t.” She takes charge in the end, but only to make his fantasy come true.

But it’s Allison who kicks off the climactic discussion about Claire’s virginity, culminating in her famous take on the Madonna-Whore complex:

“It’s kind of a double edged sword isn’t it? Well, if you say you haven’t, you’re a prude. If you say you have you’re a slut. It’s a trap. You want to but you can’t, and when you do you wish you didn’t, right?”

“A slut or a prude: The Breakfast Club as Feminist Primer,” Julianna Baggott’s essay in the collection Don’t You Forget About Me (co-edited by Sheedy), claimed this speech was instrumental at the time in formulating the sexual politics of young women like her. “The history of eighties virginity can be broken into two eras— pre-Breakfast Club and post-Breakfast Club,” she wrote. “Because that’s when the truth was first spoken—the Prude/Slut Trap, the Double-Edged Sword of our Fragile Sexuality.” Baggott and her friends were aware of gender disparities, but academic discussion around the Madonna and the whore wasn’t part of their vocabulary. “Someone had said the thing that we’d all known for a long time but hadn’t had any words for,” she wrote. “Someone had said it aloud: the truth.”

Five months later that truth was drowned out by men yet again. A New York magazine feature that started out as a profile of Emilio Estevez turned into a cover story about a new wave of young actors, “Hollywood’s Brat Pack.” David Blum’s piece hit newsstands in June 1985 and the subjects—Estevez, Nelson, Nicolas Cage, Tom Cruise, Matt Dillon, Rob Lowe and Sean Penn—have been trying to shake the moniker ever since. No ‘80s actresses faced the same issue because no ‘80s actresses were featured in the story. Blum did not write about Ringwald or Sheedy or Mare Winningham, all of whom co-starred in the films included in the article. “I’ve been called the Women’s Auxiliary of the Brat Pack,” Ringwald said two years later. The only woman named in the piece was St. Elmo’s Fire’s Demi Moore, and only within the context of her off-screen “romance” with Estevez. Apparently, women didn’t fit into the retro package the media was trying to create. “This is the Hollywood ‘Brat Pack,’” Blum wrote. “It is to the 1980s what the Rat Pack was to the 1960s—a roving band of famous young stars on the prowl for parties, women, and a good time.” The Women’s Auxiliary was more tied to the 1950s. The cyclical nature of anti-feminism—what Faludi calls the break that follows each wave of feminism—along with the conservatism of 1980s politics and media acceptance and propagation of the myth that women’s liberation made us all miserable, had united to create a backlash that held up retro femininity as the remedy.

*

Pretty in Pink is the last John Hughes film Molly Ringwald ever shot. The story about a poor teen who falls in love with a “richie” had been percolating since Hughes was in high school. Then his muse mentioned the Psychedelic Furs song. “For a long time I thought about it as a boy’s story,” Hughes said on the DVD commentary track, “and then I thought, no, I think it would be more interesting if I write it for a female.” So he wrote it for Molly—she is Andie Walsh. “The conventional wisdom in Hollywood is that movies about boys do better,” Hughes told the Sun Sentinel. “People told me that if I called the film Pretty in Pink that boys wouldn’t go.” He didn’t care. Instead, he handpicked Howard Deutch, who had cut the trailers for Sixteen Candles and Breakfast Club, to helm the film so he could focus on writing and producing (even though according to Gora, Paramount’s president of production Dawn Steel “felt that if Hughes was not going to direct the picture, a woman should”). As a result, the men vying for Andie weren’t much better than the ones in Sixteen Candles.

Andie is a senior from the wrong side of the tracks (there is a literal train track in front of her house) who attends a private high school where she gets harassed daily by trust funder Steff (James Spader), who is never wearing socks because we get the impression he is always post-coital. Andie studies hard, her best friend, Duckie (Jon Cryer dressed by Vance as an homage to British Teddy Boys ), is more interested in studying her. Otherwise, she is a veritable single mother, cooking, cleaning and working part-time at a record store to support her unemployed dad who is still not over his wife splitting years ago. In the meantime, a wet rag appropriately named Blane (Andrew McCarthy)—Steff’s best bud and heir to McDonagh Electric—falls for Andie and her “five and dime” chic. But will he take her “low-grade ass” to prom?

Blane doesn’t make rape jokes but he does class shame Andie. “Want to go home and change?” he asks on their first date. “I already did,” she deflates. He later jokes that they should hang out with her friends “under a rock” because that’s so much worse than the rich man’s slumber party he eventually forces her to go to, where the basic premise appears to be stripping down to your underwear and piggy backing a frat boy. That is when you aren’t calling Andie an “asshole” and making fun of her clothes. “I’m really sorry for bumming out the night for you”—yeah, Blane doesn’t say that, Andie does. She’s apologising for not wanting him to see where she lives even though his behaviour up until that point provides a perfect reason not to. Her reward for being a doormat is an invite to the prom. So she kisses him, which, oddly, is the part Ringwald had a problem with. “It really embarrassed me as a girl to be the one that initiates the kiss,” she said, “because I always thought, ‘What? No, you wait for the guy to kiss you.’”

Duckie Dale would have been more than happy to oblige. The role of Andie’s best friend was originally written for Anthony Michael Hall and is consequently a general facsimile of the geek from Sixteen Candles. Duckie believes that because he rides his bike past Andie’s house repeatedly and spends hours waiting for her outside a club with misogynistic Andrew Dice Clay, she owes him something. “I live to like you,” he argues when Andie tells him she is going out with Blane. Duckie can’t believe his ears because he just spent several minutes performing a Kenny Ortega routine for her to “Try a Little Tenderness.”

Duckie is not only clingy, he’s overconfident. Despite being tutored by Andie so he doesn’t flunk out of school, he tells her father, “My only future plans are to make sure she’s taken care of and I’d like to marry her.” At least Andie’s father attempts to convince him that he can’t “make it happen.” But then, following his Redding routine, Duckie gets confused when Andie cries about her date being late. “Is this like one of those Feminine Mystique deals or something?” he asks. Jason Diamond considers it a realistic offhand comment—“I could see that being a 17 year old high school kid and he just knows the word, he might not even know what it means”—but it seems to speak more to Hughes’s adolescence than to Duckie’s. The filmmaker was a teen in the ‘60s, which is when Betty Friedan’s consciousness-raising tome for suburban housewives sparked the second wave. That Hughes dismisses it as the punchline to a glib remark suggests he doesn’t take women’s lib entirely seriously. And his treatment of Iona supports that.

Andie’s new wave fairy godmother, played by Annie Potts, is a spiky haired rubber dressed punk (Vance modeled her on Sade) who manages a record store and dumps her boyfriend for treating her like Betty Crocker: “I cook for you, I do your laundry, I sleep with you, now you want a ride to work? Grow up!” She also acts as Andie’s confidante, a rare role for a female friend in Hughes’s work. No longer being a young woman seems to shield Iona from being a Madonna or a whore, but not a material girl: Iona complains about working in a “lowly retail outlet” despite being a manager at a time when women were largely relegated to supporting roles. When Andie responds that it’s not a loss if she’s good at it, Iona replies, “I’m good in bed, should I be a whore?” In the Reagan era—when living well was the best revenge—the fact that Iona’s job is financially unsuccessful is held up as tantamount to what Hughes sees as moral compromise.

“In so many of these movies, it is as if Hollywood has taken the feminist films and run the reels backward,” Faludi wrote. “The women now flee the office and hammer at the homestead door.” Towards the end of Pretty in Pink, Andie stops by Iona’s place, only to be met by a very tall man in a suit who apparently owns a lucrative pet store. Iona is in the bathroom singing “Copacabana”—“Don’t fall in love”—and emerges to reveal her “normal” makeover (if a department-store sea captain with secretary hair is normal). “Either it’s all those drugs I took in the ’60s or I’m really in love,” she says. “He’s a yuppie but he’s so nice. He’s employed, he’s heterosexual, I swear to God, I’m so far ahead of the game next time you see me I’ll probably be picking out my China patterns.” It’s the drugs. It’s got to be because Iona does such a 180 that not even the woman who played her bought it. “I looked at that today and thought, ‘Oh surely that didn’t last,’” Potts said on the DVD in 2006. Four years later, for Pretty in Pink’s Entertainment Weekly reunion, she added, “Everybody tends to get a little more conservative as they get older. That didn’t make sense there, though.”

Neither did Andie’s coda. She should have skipped prom and saved Iona from that towering yuppie, then taken her on a Thelma and Louise-style road trip in her frosted pink VW, leaving both Blane and Duckie with their dicks in their hands. Instead she takes Iona’s ‘60s prom dress and the ‘80s monstrosity her dad gives her (Vance says it was originally a quinceañera dress) and turns it into a lace-and-polka dot off-the-shoulder-slouchy-straight something-or-other that Ringwald hated. “She wanted to have a full strapless like all the other girls,” says Vance, explaining, “A full skirt just didn’t work for who she was.” Because of this dress, Hadley Freeman calls Pretty in Pink the “anti-makeover film.” She considers it “an inspiration to any girl or woman who felt like they should alter themselves to appeal to others.” In her baby pink war paint, Andie marches off to prom where a lone Blane simpers, “You don’t need me to say I’m sorry,” before accusing her of not believing in him. Still, he tells her he loves her and that’s good enough so she runs after him and kisses him in the parking lot, dropping her purse in a puddle even though it’s worth more than he is.



“It wasn’t in the spirit of the movie,” Pretty in Pink producer Lauren Schuler Donner says of the film’s conclusion. “To me it was just contrary to what the movie was trying to say.” She and co-producer Ned Tanen preferred the original ending, the one in which Andie ends up dancing platonically with Duckie to David Bowie’s “Heroes.” But Ringwald hated that ending as much as she hated that dress. “As a teenager I felt she should’ve ended up with the guy she wanted to be with,” she told Brett Easton Ellis last year on his podcast. Hughes took her advice.

“Her opinion carried more weight than anybody else’s did,” Cryer said in You Couldn’t Ignore Me. And Ringwald’s stance was supported by test audiences who reportedly booed the original ending. “The audience wanted the fairy tale,” says Donner, “that’s why you go to the movies, to escape.” Hughes, forever fearing disappointment, appeased them. “I have no interest, none whatsoever, in doing something for myself instead of for the audience,” he told the Times. “My movies are popular because they do what they’re supposed to do.” And what they’re supposed to do is give us what Hughes always wanted and believed we wanted too—more. “He was a marketing guy to begin with and he was always a marketing guy so he didn’t shy away from changing his own stories if the public was asking for something better,” Honeycutt says. To Hughes, to the Reagan years, better was the poor awkward looking girl landing the rich good looking guy. “Forget the politics,” he said, “teenage girls aren’t interested in the politics.”

*

Molly Ringwald landed the cover of TIME in May 1986, a few months after Pretty in Pink premiered, and, according to Gora, it was the “greatest apex” of her fame. The smiling 18-year-old was featured in lace—white, not pink, this time—with red lips and red hair, next to the words, “Ain’t She Sweet.” But her quote about Hughes had the industry questioning the cover line. “When John moved from Chicago to L.A. after The Breakfast Club, he changed. I wouldn’t say he ‘went Hollywood,’ but he started looking very GQ,” she said. “I don’t really see him anymore. I still respect him a lot, and if he gave me a good script, I’d read it. But I don’t think we’ll work together again real soon.” Though Hughes himself was quoted in the article, according to A Life in Film he would later claim they were not his words and criticize Ringwald’s cover treatment: “I mean, God, there are so many things going on around the world.” Hughes, who moved back to his hometown of Chicago soon after making it big in Hollywood, never rated fame particularly highly. Only three years earlier, he chose Ringwald to star in his first film because she was on the correct side of the following question: “Is someone more interested in being on the cover of Tiger Beat and People magazines, or is he or she interested in being in this business a long time?”

According to Ringwald, she and Hughes actually fell out two years before the TIME cover. “If he thought that I did something that slighted him, if he got jealous, he would go into a rage and not talk to me for a couple days,” she told Brett Easton Ellis. “And this happened a couple times until finally at the end of Breakfast Club we just stopped talking completely.” According to Breakfast Club producer Michelle Manning, this was around the time she noticed Ringwald and her co-star Anthony Michael Hall picnicking under a tree. “As Molly was getting closer to Michael, John may have pulled away a bit,” she says. The couple was only together “for a few months” but Ringwald admitted in VF that when Hughes found out, “He did not like it at all.” While this would suggest he had romantic feelings for his protégée, Ringwald denied it. “I think there must have been a crush but honestly it didn’t feel sexual to me,” she told Ellis. “And he certainly never made any kind of a pass at me.”

John Hughes had lost control of his muse, that’s why he dropped her. It’s clear from the anecdote Ringwald shared about booking a doctor’s appointment during one of their collaborations. “John was sure that I was meeting with someone for another movie,” she told VF. “He flipped out. He thought that I was not committed to him.” It’s clear from the scores of people he dropped for telling him, “no,” which Ringwald had also done (she passed on Some Kind of Wonderful, finding it too similar to Pretty in Pink). It’s clear from the Spy magazine exposé in which a number of insiders painted him as a “big, powerful child” who bullied his staff. It’s clear from him moving his entire production team to Chicago to maintain control of his films. It’s clear from his long-time production partner, Ned Tanen, who said Hughes liked to work with actors he could control. “I wanted to grow up, something I felt (rightly or wrongly) I couldn’t do while working with John,” Ringwald wrote in a Times op-ed following Hughes’ death in 2009. “Sometimes I wonder if that was what he found so unforgivable.”

*

There is very little pink in Some Kind of Wonderful, but that is to be expected since Hughes’s last teen film is, as Hadley Freeman describes it, a “gender-reversed Pretty in Pink.” Keith Nelson (Eric Stoltz) falls in love with uber feminine wannabe richie Amanda Jones (Lea Thompson), who is from the same side of the tracks as him and his “tomboy” best friend, Watts (Mary Stuart Masterson), who in turn happens to be in love with Keith. It’s the kind of love triangle we’ve seen numerous times, but the corners are new. Stoltz wears so much makeup and is so beautiful that it’s not hard to imagine Pretty in Pink’s Stef calling him a “bitch.” While Masterson, with her bleached blond bowl cut, men’s boxers and white undershirts, is designated a “lesbian” by her classmates because apparently none of them have seen The Legend of Billie Jean at the local multiplex. Even their interests—painting for Keith, drumming for Watts—break traditional gender norms to such an extent that Hughes initially referred to Watts only as Drummer Girl.

“I gave all these notes,” Masterson said in You Couldn’t Ignore Me, “like, ‘This character is written as a tomboy. But I don’t think tomboy is necessarily a woman that wants to be a man. It’s somebody who’s just not willing to be a slave to the feminine manipulative paradigm.’” She was the reason Watts’s hair looked the way it did, it broke off after she DIY lightened her dark red dye job from a previous film. Masterson also quashed the choice to name her character Keith—“Why does she want a guy’s name?”—and suggested boxer shorts over figure-hugging briefs. “These were things that seemed really important to me at the time,” she said.

She had the right audience for it. Some Kind of Wonderful’s original director, Valley Girl’s Martha Coolidge, was the first woman to helm a teen Hughes film. “Her vision was almost like a dark, silent film,” Stoltz said in You Couldn’t Ignore Me. “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.” His appearance complimented her interpretation—long greasy shoulder-length hair, “because the guy was someone who wasn’t able to fit in, we thought that was a great way to go,” Stoltz told Movie Hole in 2007. But four days before shooting, Coolidge was suddenly fired. “There were no signs of any problems,” she told the blog Kickin’ it Old School in 2011. Tannen later explained to her, “this was a whim of John’s, but John was very important to the studio so they had to do it even though it would hurt the film, and me.” Hughes never apologized and the only female director he ever worked with remained Amy Heckerling (European Vacation). “If he wouldn’t put people of colour in his movies, if he wasn’t going to try to upset the status quo a little bit in that regard,” says Jason Diamond, “it’s hard for me to imagine that he would have gone to bat to have a female director.” Hughes’s job as he saw it was to present the ‘80s fairy tale, patriarchal white suburbia—his own life, basically—not to replace it with something better.

With Howard Deutch directing, Some Kind of Wonderful lost its darkness. Amanda, who looks like an extra from a Bon Joni video or perhaps Bon Jovi himself, is dating Hardy Jenns (Craig Sheffer), the kind of boyfriend who calls you his “property,” before jilting him for flirting with a young Chynna Phillips. Barely single, she agrees to a date with Keith, a less creepy alternative who nonetheless gazes at her so long he can virtually reproduce her image on canvas. As Watts puts it, “It must be a drag to be a slave to the male sex drive.” But Amanda knows she “is sex,” and uses this to access the privileged class. Even Watts can’t help but stare at this wonder of ‘80s femininity—pop socks + camisole!—in the girls’ change room. “This is 1987, did you know that a girl can be whatever she wants to be?” Watts asks as a guy drools over her. She doesn’t want to be Amanda Jones, but she does want what she has: Keith. How to have one without being the other? It’s a feminist dilemma. “Pretend I’m a girl,” she tells Keith, before engaging in a steamy make out session with him. And the only thing he can think of to compliment this “tomboy” after seeing her blush is, “That was very nice, you’re pretty!”



The trouble with Watts, who Hughes called one of his “best characters,” is that she is ultimately defined by Keith. “It was an attempt to see if the geek could get the girl and work,” Hughes told The Hollywood Reporter. And the way he gets the girl is, of course, through an Allison-style makeover that masks her edge. Watts covers her tattoo and puts on lipstick, a bra and a form-fitting black silk outfit (at least it isn’t pink) and takes out her punky row of earrings. In the final scene Keith chases after this feminized version of his best friend as she walks blubbering down the street and kisses her—lifts her off the ground, no less—then hands her the diamond earrings he bought Amanda with his college money.

Watts: I wanted these, I really wanted them.

Keith: You look good wearing my future.

In an earlier version of the script, Keith reportedly proposed as well, but the final shot was bad enough. In an interview for Some Kind of Wonderful’s EW reunion in 2012, Masterson was still frustrated by it. “All anyone says to me a quarter of a century later is, ‘I love that part where you get the earrings,’” she said. “It’s weird! This materialistic aspect is not who Watts is. She would have walked away victorious, and then to the pawnshop.” Alyx Vesey at Feminist Music Geek wrote, “I do think there’s a valid argument to make for how heterosexuality may contain and stabilize Watts and thus render her as less of a threat.” And a threat she is, not just sexually, but to traditional femininity. “Watts is grouchy, snarky, tough, insecure and sometimes downright mean,” Kate Harding said in Salon in 2009 in a piece about Hughes heroines. “She has no knack for the sort of performative femininity that helps Amanda Jones (Lea Thompson) transcend her wrong-side-of-the-tracks background among the rich and popular, so she can only deflect their derision with an endless supply of snappy comebacks—and, often enough, snappy pre-emptive strikes.”

Some Kind of Wonderful only made $18.6 million when it was released in 1987, the lowest box office for a John Hughes film at the time (for comparison, Sixteen Candles raked in $23.7 million, The Breakfast Club $46 million and Pretty in Pink $40.5 million). It’s apt that his attempt at subverting convention announced the death of an oeuvre that often upheld it. That the one film in which the fairy tale ending does not involve the oddball playing ball with the richest, hottest and most popular alternative did not sell out. Hughes had disappointed an audience that had acclimated to the Reagan era’s acquisitive anti-feminism. It follows that, in recent years, these movies, in which he presented women within the ‘80s male paradigm, have inspired predominantly male directors (Kevin Smith, Todd Phillips, Judd Apatow, David Dobkin at al.) The final scene of Sixteen Candles warned us:

If you were here

I could deceive you

And if you were here

You would believe

And we did. But not anymore.