With When Romance Met Comedy, Caroline Siede examines the history of the rom-com through the years, one happily ever after (or not) at a time.

John Hughes built a career on exploring teenage archetypes. The Breakfast Club famously featured a brain, an athlete, a basket case, a princess, and a criminal. For the two other films in his trilogy of collaborations with Molly Ringwald—Sixteen Candles, which he wrote and directed, and Pretty In Pink, which he wrote but didn’t direct—Hughes explored a slightly different set of archetypes: a nerdy outcast, a rich prince, and a plucky but put-upon everywoman. Sixteen Candles and Pretty In Pink don’t feel like exactly the same movie (in fact, Hughes would more obviously remake Pretty In Pink in the lesser Some Kind Of Wonderful), but they’ve got a lot of the same pieces in place. Yet it’s the different ways in which those pieces are assembled that highlight why Pretty In Pink is worth remembering while Sixteen Candles is maybe better off forgotten.

To be honest, it’s a weird time to talk about John Hughes. Shortly after I decided to tackle Hughes’ generation-defining teen rom-coms for this column, Vox’s Constance Grady published an incisive piece using Sixteen Candles’ horrific date-rape-as-comedy subplot to explain the prevalence of 1980s rape culture. It echoed a lot of things Ringwald herself explored earlier this year in a fantastic New Yorker essay grappling with Hughes’ artistic output in the #MeToo era. While researching this article, I also came across a bunch of upsetting anecdotes about Hughes’ petulant off-screen behavior. There are no egregious accusations in Hughes’ background, just stories of a deeply insecure man with a nasty temper who could hold a vindictive grudge. After taking on a 15-year-old Ringwald as his friend and muse—he wrote Sixteen Candles based on her headshot and then wrote Pretty In Pink after he actually knew her—Hughes suddenly cut her out of his life without explanation, barely even speaking to her on the Pretty In Pink set. “It was very hurtful. And it still hurts,” Ringwald told David Kamp for his incredibly thorough 2010 Vanity Fair profile on Hughes’ life.

Retrospectives about Hughes tend to romanticize his remarkable ability to capture the Gen X teenage experience despite being an adult Baby Boomer. (Hughes was in his mid-30s with two elementary school-aged kids when he was making his iconic catalogue of 1980s teen movies.) But it’s also hard not to wonder if Hughes was just suffering from a form of arrested development that was being coddled and enabled by the Hollywood system around him (and National Lampoon magazine before that). I haven’t made it a point within this column to analyze the off-screen conduct of rom-com creative forces, although I don’t necessarily think that should be off-limits when discussing art. In this case, however, it feels especially relevant because there’s a real streak of casual cruelty and unchecked male entitlement running through Sixteen Candles, which is one of the reasons I think Pretty In Pink is the far superior film.

When it was released in 1984 as Hughes’ directorial debut, Sixteen Candles was praised for being an earnest, female-centric teen rom-com that stood in sharp contrast to sex-crazed, male-focused teen comedies like Porky’s. In retrospect, however, it’s the Porky’s-like elements of Sixteen Candles that stand out, including a leering shot of the bare breasts of a character who’s still in high school. In addition to the film’s overtly problematic aspects (including the cringe-worth racist caricature Long Duk Dong), Sixteen Candles has a massive tonal problem. It’s half quiet teen dramedy, half over-the-top raunchy farce, which makes it hard to invest in either portion of the film. Though Sixteen Candles has a ton of affection for Ringwald’s 16-year-old Samantha Baker, it thoughtlessly presents the rest of its young female characters as objects of cruel ridicule. Yet it has nothing but compassion for its male teens, no matter how horrifically they act.

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Released two years later in 1986 (Hughes made The Breakfast Club in between), Pretty In Pink is not only a more tonally consistent film, it’s also a much more empathetic and thoughtful one. Ringwald stars as Andie Walsh, a self-possessed high school senior with an eclectic wardrobe, which is both evidence of her status as a cool, artsy outsider and a by-product of the fact that she can only afford to shop at thrift stores. In a high school with a huge class divide, Andie comes from the wrong side of the tracks, which soon becomes a point of contention in her burgeoning relationship with Blane McDonough (Andrew McCarthy)—a rich kid who’s a better person than the rest of his “richie” friends, but still pretty naïve about the cruelty of his privileged world. Pretty In Pink locks into its condemnation of male entitlement right off the bat. Before she’s even met Blane, we see Andie fend off the advances of his friend, Steff (James Spader, oozing so much entitled smarm he might as well be sentient slime in a white linen suit). Throughout the rest of the film, Steff keeps trying to manipulate Blane into dumping Andie, ostensibly under the guise of saving his friend from associating with working-class trash. In actuality, however, Steff is just pissed that Andie wouldn’t sleep with him and therefore vindictively trying to ruin her life in whatever way he can. It’s an observation that still feels insightful today.

Though Sixteen Candles and Pretty In Pink are both about handsome, rich guys falling for girls outside their usual social circles, they offer two very different kinds of romantic fantasies. In Sixteen Candles, Sam is an endearing but passive character who doesn’t really play a role in her own love story. The fantasy is that she gets the guy without even trying. (Like Sleeping Beauty, she even spends a good chunk of the movie asleep.) Pretty In Pink, meanwhile, is a Cinderella story in which Andie plays her own fairy godmother. “I just want to let them know that they didn’t break me,” she tells her dad as she prepares to head to the prom alone in a dress she sewed herself. When she gets back together with Blane, it feels like something she’s earned, rather than something she’s magically been given. It’s still a fantasy, but it’s a fantasy in which Andie has a whole lot more agency.

To be clear, I don’t think it’s bad to enjoy the more simplistic romantic fantasy of Sixteen Candles. I know that for many people, Michael Schoeffling’s senior dreamboat Jake Ryan is up there with Mr. Darcy in terms of romantic icons, and the fact that Jake’s largely a blank slate on which to project your desires is kind of part of his appeal. But the pure wish fulfillment plotting of Sixteen Candles definitely makes it a far less complex film. The final shot of Sam and Jake perched over a birthday cake is gorgeous, but it’s also the first time they’ve ever spoken to each other. We don’t even really know what Jake likes about Sam other than the fact that she idolizes him.

In Pretty In Pink, meanwhile, we get to watch Andie and Blane develop chemistry, start a relationship, and work through their issues as a couple. As my A.V. Club colleague Noel Murray once put it, “For someone whose movies followed such predictable, reliable arcs, Hughes had a high tolerance for the unexpected. And it’s those moments—the weird gestures, the odd lines, the serious turns—that make his movies so enduring.” Andie’s world is full of wonderfully specific oddities, from her sisterly friendship with her offbeat employer Iona (a great Annie Potts), to her passion for new wave music (the film has a stellar soundtrack), to the deadpan way she and Blane initially flirt over a Steve Lawrence record.

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To be fair, I don’t think either film’s romance works quite as well as it could. On paper, Jake is an entitled asshole, but because Sixteen Candles doesn’t realize how horrific his actions are they’re easier to overlook. (For the record, those actions include bragging about how he could “violate” his unconscious girlfriend 10 different ways and then handing her off to be raped by his friend—all of which is played as comedy.) In contrast, Pretty In Pink tries to give Blane an actual arc about grappling with his entitlement, but it can’t quite come up with a satisfying resolution so he just kind of peters out as a character. Which romance you prefer might just come down to which actor you prefer—the brooding physical confidence of Michael Schoeffling or the warm, off-kilter energy of Andrew McCarthy. For her part, Ringwald fought to cast the less conventional McCarthy in Pretty In Pink despite the fact that the filmmakers were originally looking for a more traditional jock-type. Like Ringwald, I really enjoy the weird, wide-eyed way McCarthy plays Blane. But McCarthy’s endearing performance actually turned out to be a problem for the filmmakers.

Pretty In Pink was originally supposed to end with Andie choosing her nerdy, lovelorn best friend, Duckie (Jon Cryer), over Blane. But as director/frequent Hughes collaborator Howard Deutch told The Huffington Post in 2016, “The ending didn’t work in the test screening… That shocked everyone because the architecture of the story was that love endures and overcomes everything. The girls in the test screening didn’t go for that. They didn’t care about the politics; they wanted her to get the cute boy. And that was it. So we had to reshoot the ending.” Though Deutch may have disdain for the “girls” who didn’t get the “politics” of his film, I’m definitely with them on this one. The fact that Andie doesn’t get together with Duckie is the best, most interesting thing about Pretty In Pink. In fact, so much of what I like about the film comes down to Duckie’s bittersweet narrative that it’s genuinely hard for me to believe it wasn’t baked into the story from the beginning. As it plays out in the final film, Pretty In Pink is a masterful, empathetic deconstruction of male entitlement that doesn’t give nerdy guys a pass just because they’ve faced social struggles elsewhere. It’s perhaps deeply telling that Hughes only stumbled into it accidentally.

Duckie is by far Pretty In Pink’s most divisive element. In addition to a vocal contingent who thinks he should’ve ended up with Andie, I’ve also seen Cryer’s work dismissed as just a lesser version of the hilarious, heartbreaking stuff Anthony Michael Hall previously did as Hughes’ go-to nerd. (Hughes apparently wrote Duckie with Hall in mind, but by that point Hall was ready to take on different kinds of roles.) I’d argue that rather than being lesser, Cryer is just giving a very different kind of performance than the one Hall likely would’ve given. In Sixteen Candles, Hall makes geeky “Farmer Ted” endearing in even his most annoying moments. In Pretty In Pink, Cryer makes Duckie annoying in even his most endearing ones.

And that totally works! In Cryer’s hands, Duckie’s performative demeanor—which feels like a cross between a 1950s hipster and a 1940s comedian—has a deeply uncomfortable edge of neediness, which makes it a wonderfully realistic rendering of teenage desperation. The movie is sympathetic to Duckie’s struggles (unrequited love sucks!), but it’s also deeply critical of the cruel, petulant way he treats Andie as soon as she starts dating Blane. What works about Duckie’s story is what works about Julia Roberts’ arc in My Best Friend’s Wedding: He does the hard work of challenging the idea that he deserves to be the hero in Andie’s romantic narrative, and that becomes its own bittersweet happy ending for him. Andie’s romance with Blane probably isn’t built to last, but her friendship with Duckie is, now that he’s learned to accept it as a genuine friendship rather than a precursor to romance.

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It’s hard for me to wrap my head around the idea that Hughes originally wanted a different ending, because that bittersweet thread seems to be so purposefully woven into the film. Duckie gets an overt cautionary tale in Andie’s father, Jack (a wonderful Harry Dean Stanton), a man who was blind to the fact that his wife never loved him in the way he loved her and is still struggling to function three years after she left him. As Jack wisely advises Duckie, “You can love Andie, but that doesn’t mean she’s gonna love you back. It doesn’t mean she won’t. But what I’m trying to say is you can’t make it happen. It either will or it won’t.” It’s hard to imagine that scene taking place in a film that ends with Duckie basically strong arming his way into a romantic relationship through sheer force of will.

Because Sixteen Candles was Hughes’ first big teen movie, it got a lot of credit for things Hughes would go on to do much better in his future teen films. For instance, Sixteen Candles also has its own moment of a nerdy guy learning to see the object of his affection as a complex human being. In the film’s best scene, Ted and Sam sweetly bond in a half-finished car in their school’s autoshop. But Sixteen Candles never builds on that dynamic in any meaningful way because Ted quickly gets sucked into the worst elements of the farcical sex comedy stuff. Ted may have learned to see Sam complexly, but that doesn’t go for the unconscious prom queen he accepts as his plaything.

So much of Pretty In Pink feels like a direct rebuttal of the unbridled male entitlement on display in Sixteen Candles, that I’d be more willing to praise Hughes for evolving as an artist if I didn’t know about the way he was treating Ringwald on set. (Hughes later cut ties with Hall as well, someone who once considered himself a surrogate son of the Hughes family.) I don’t have any answers on how to parse Hughes’ complex personal and artistic legacy, nor do I have any answers about how best to grapple with the problematic stuff in his oeuvre, other than to once again encourage everyone to read Ringwald’s nuanced New Yorker essay. But I do know that given a choice between watching Sixteen Candles or Pretty In Pink, I’m always going to go with the latter. Its creator may have been imperfect and its successes may have been accidental, but it’s still got a whole lot of relevant stuff to say about teenage romance.

Next time: We investigate How Stella Got Her Groove Back.