Duckie and Andie’s father, Jack, make for an odd pair as they bond over Budweisers and juice boxes in Pretty in Pink, which originally hit theaters on Feb. 28, 1986. But John Hughes' coming-of-age film trades in odd pairs: Andie (Molly Ringwald) and Blane (Andrew McCarthy), Andie and Duckie (Jon Cryer), Blane and Steff (James Spader), on and on. Despite its strange constellation of characters, everyone in Hughes' most mature teen romance has something in common: Nobody is getting the love they want, need and think they deserve.

“You can love Andie, but that doesn’t mean she’s gonna love you back,” Jack, played by Harry Dean Stanton with just the right mix of wisdom and tragedy, tells Duckie. “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.”

Despite Jack outlining Pretty in Pink’s message in a few quick lines, nobody in the film — including Jack, who is still pining for a wife who left him three years ago and is never coming back — can stop trying to make it happen.

Though directed by Howard Deutch, Pretty in Pink remains quintessential John Hughes, who wrote and executive-produced the film. Like The Breakfast Club, which Hughes wrote and directed a year before, Pink explores the emotional lives of teenagers with honesty, insight and humor. What’s new here is seeing the teens evolve over time in their natural environment, learning that heartbreaks will keep piling up well into adulthood.

Hughes’ cinematic impact has been massive — his approach and aesthetic can be felt in everything from Wes Anderson and Kevin Smith movies to the Harry Potter series. But the more we learn, the more we discover that so much of his genius depended on luck, trial and error and happy accidents.

The bard of ’80s adolescence, Hughes actually had a bumpy career. He created half a dozen cult classics and box office staples but also made flops – Pretty in Pink was a solid hit, making $40 million on a $9 million budget, but not a blockbuster. He also bounced between the crushing loneliness of being misunderstood or excluded (Pink; Breakfast ClubPlanes, Trains and Automobiles) and juvenile humor that ran from stupid to silly to darkly regressive, definitively criminal and just plain racist (see Sixteen Candles, Weird Science, much of the Home Alone franchise). In Pretty in Pink, he’s at a zenith, and a lot of that has to do with Ringwald — she provides a bold, measured look at their relationship in this essay.

The third movie the pair made together (and the second he explicitly wrote for her), Pretty in Pink follows the rocky romance of the literally-from-across-the-tracks Andie and “richie” Blane. Between their on-and-off relationship and reckoning with class, we get loads of other characters with even less luck finding love.

Andie’s best friend, Duckie — a unique blend of dork, geek, greaser, hipster and charmer — relentlessly, hopelessly, awkwardly pursues Andie. Iona (Annie Potts), Andie’s boss at the record store, can’t seem to both be herself and find a partner. Blane’s friend and foil, Steff, tries to make Andie another trophy early on and spends the rest of the movie attempting to sink his friend’s relationship with someone who “was, is, and will always be nada.” And Jack, with his chronic hangdog look, is just a mess. For most of the movie, every character pinballs between angst, anguish, anger and inertia as the teens' senior year sputters toward the prom.

Ringwald’s influence comes from pushing for McCarthy to be cast as Blane. The role nearly went to Charlie Sheen, but Ringwald, as revealed in Susannah Gora’s book You Couldn’t Ignore Me if You Tried: The Brat Pack, John Hughes, and Their Impact on a Generation, told Hughes and Deutch, “That’s the kind of guy I would fall in love with.” That came through in the couple’s chemistry. Everything about their relationship — the looks and kisses, the painful awkwardness that dominates so many of their interactions — feels real.

If Hughes got lucky taking Ringwald’s advice, he found a happy accident in turning Cryer into Duckie. Ringwald thought Robert Downey Jr. would work. Hughes liked Anthony Michael Hall, who passed on it. Cryer landed the part and came to define the decade's most distinctive teen movie outsider.

As often as not, the film finds its emotional center in Duckie. He looks and thinks like a kid (compared to Andie, who grew up fast when her mom left her to take care of her boozing, unemployed dad). But he kisses like a man, dresses like a Stray Cat, loves Otis Redding, seems to have a sad, solitary home life and delivers jokes like a Borscht Belt comedian. Time has determined his best barb to be, “His name is Blane? Oh! That’s a major appliance; that's not a name!”, which Cryer improvised. (He also ad-libbed his line about the tampon dispenser in the girls’ bathroom being a candy machine.) But let’s not forget the glimmer of insight that follows that line: “Here's the point, Andie: I'm not particularly concerned with whether or not you like me. ‘Cause I live to like you, and I can't like you anymore.”

So Hughes got lucky. But he also grew up a little bit with his teen muses after some hit-and-miss earlier works. He managed to banish the crass, dumb, puerile jokes he loved so dearly and really dig into the lovelorn across generations and income tax brackets. Much of the writing is sharp and smart. Even magic is found in Steff and Iona, Andie’s boss at the record store.

Steff seems like both an archetypal teen snob and a stoned stockbroker in a half-buttoned shirt who wandered into a high school looking for a cigarette machine. But he has an authenticity. In one of Hughes’ most insightful moments, Steff says, without irony, “Money really means nothing to me. Do you think I'd treat my parents' house this way if it did?”

Iona, who acts as a stand in for the older sister Andie doesn’t have, offers some Zen wisdom on going to the prom: “I have this girlfriend who didn't go to hers, and every once in a while, she gets this really terrible feeling, you know, like something is missing. She checks her purse, and then she checks her keys. She counts her kids; she goes crazy, and then she realizes that nothing is missing. She decided it was side effects from skipping the prom.”

The movie does so much right. The fashion rightly runs from Cyndi Lauper vintage to Don Johnson swagger. Minor characters played by Andrew Dice Clay, Kristy Swanson, Dweezil Zappa and Gina Gershon lock in with the tone. To this day, the no-filler soundtrack remains hip thanks to songs by the Psychedelic Furs, New Order, INXS, and Echo & the Bunnymen. If the film gets the ending wrong, well, maybe that works for a piece of art obsessed with unbalanced love.

Infamously, Deutch had to reshoot the ending. Originally, Andie and Duckie ended up together — if not romantically, then at least on the prom dance floor. But test audiences hated it. They wanted Andie and Blane to get back together. (Of course they did — they were made up of love-hungry teens.) So Deutch had to pull the cast back together and, with Orchestral Manoeuvres in the Dark’s “If You Leave” pumping out of the PA system, Blane tells Andie, “You told me you couldn't believe in someone who didn't believe in you. I believed in you. I always believed in you. I just didn't believe in me. I love you...always.” And with that, a generation of teen hearts melted to puddles on the floor.

Some say the re-shot ending didn’t work because the early scenes push toward a Duckie and Andie future. Others think it made perfect sense. But maybe the ending is actually the least important part of the film. After all, nobody now thinks a 50-year-old Andie would be married to Blane or Duckie.

Maybe the important thing for anyone lost in love — or lost without the love they think they need — is making sure it doesn’t break you along the way.


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