The first time I saw Pretty in Pink, John Hughes’s enduring rhapsody for the young, I was in the second grade. My sixteen-year-old babysitter brought over a VHS copy she’d picked up from the local drugstore, which rented videos, and made me promise not to tell my parents she let me watch it with her.
“It’s for older people,” she said, which made me think we were about to watch something with a lot of swear words and naked people. While I thought all the characters looked cool — even then I could appreciate how James Spader rocked an unbuttoned shirt, how Molly Ringwald looked great in everything — the film’s core exceeded my grasp. Its inspection of cliques and class is, uniquely, in a teenage vernacular: Ringwald’s effortless heroine, Andie, literally lives on the other side of the tracks from wealthy Homecoming King types Blane and Steff. I wouldn’t understand the nuances of the plot until I was a teenager myself, but I didn’t need teenage experience to fall in love with Pretty in Pink‘s soundtrack.
A perfectly placed song is something anyone can understand. Can you imagine any other song opening up Hughes’s film except the eponymous Psychedelic Furs track? Jon Cryer couldn’t have lip-synced to anything but “Try a Little Tenderness”; it seems wrong that the climax of every prom, everywhere, isn’t “If You Leave” by OMD. Hughes knew just how much a certain song’s placement could change how the viewer perceives the scene, how music — whether it’s on a screen or actually taking place — can be everything.
That knack wasn’t a coincidence: Hughes worked in advertising before making movies. He knew how to bottle emotion, and he did it in all his films. When John Bender raises his fist in the air at the end of The Breakfast Club, we hear the defiant first line of “Don’t You (Forget About Me)” by Simple Minds; you can’t listen to Wayne Newton’s then-thirty-year-old version of “Danke Schoen” without visualizing Ferris Bueller lip-syncing it on a parade float; and if for some reason you saw 1988’s She’s Having a Baby, I’ll bet the only thing you remember about it is how Hughes knew just when to play Kate Bush’s “This Woman’s Work.”
Although Hughes had handed over the directorial reins to Howard Deutch, Pretty in Pink was the highest expression of his elegiac style. There’s all that raw teenage emotion, packed into fantastic clothes; the soundtrack is structured like the mix you’d give a crush during sophomore year, or in a last-ditch attempt before graduation to confess how you’ve felt all along, before you go your separate ways. Why else would the physical soundtrack, the one you actually buy, start with “If You Leave,” the last track you hear in the film, and end with The Smiths’ “Please, Please, Please, Let Me Get What I Want”? You don’t fill out a mix with a Smiths song, especially one about wanting something you feel you’ll never get, unless you mean to.
It would be years before I understood any of this: before I’d have my first unrequited love, my first serious heartbreak, the kind of Big Feelings I’d first seen play out in that contraband VHS. In other words, it would be years before I’d make a mixtape. Sure, I first got obsessive about music in the CD-saturated 1990s, and I initially heard early Pavement songs and rare hardcore singles as MP3s, but I always preferred cassettes. At the beginning, I made mixtapes for myself. Back before you could drag and drop songs into a folder or share them on Spotify, I spent hours laboriously plotting out and executing tracklists, making sure the songs synced up perfectly, working to get just the right length of pause between where one number ended and the next kicked in.
As I grew more confident, I tried pulling off little tricks, like following Sonic Youth’s “Pacific Coast Highway” with the original version of “Hot Wire My Heart” by Crime, which Sonic Youth covers as the follow-up track on Sister. When I finally thought I had enough experience, I started making mixes for others. I learned that the process itself is an intimate act: Even as the producer, you still had to be the listener, paying serious attention to everything from sequencing to skipping songs that might send a weird message to the recipient. Making mixtapes was how I truly fell in love with music, and only songs I really knew and loved made the cut. Certain ones appeared on nearly every mix, like Liz Phair’s “Help Me Mary” or “The Magic Bullet Theory” by Texas Is the Reason, both of which I used to bring things down after the intensity of a Bad Brains cut. Others I added hoping to subtly say something to the person who was going to listen to it. What I couldn’t put into words, I’d put on a tape: “Freak Scene” by Dinosaur Jr. (“The weirdness flows between us”), the obligatory Cure song, even something like “Hope” by the Descendents: “But I know my day will come/I know someday I’ll be the only one.” This was how I could tell someone, “Hey, I’m a crazy ball of feelings and I really like you, but I don’t know how else to say it. Hopefully this isn’t weird, and also hopefully you still own a cassette player.”
Even though I was just starting kindergarten when it was released, the songs on the Pretty in Pink soundtrack put me in a different place and time. I was a child when Suzanne Vega first sang “Left of Center,” the song in the background when Andie asks Duckie what they’re going to do in a year, when they aren’t in high school anymore. Echo and the Bunnymen wrote “Bring on the Dancing Horses” specifically for the film; today it’s my favorite song by the band. The Smiths and New Order have been old standbys ever since I first heard them on the soundtrack decades ago. Sure, I was in high school in a later decade, but this specific collection brings me back to being the kind of teenager Hughes tried to portray: repeatedly hitting the stop and record buttons on a cheap boombox, crafting the perfect mix, complete with the fidelity that only a dubbed cassette tape can offer, to let somebody know how I felt. And that’s exactly why the film and its soundtrack hold up so well to this day: plain, simple feelings. When we’re young and don’t know any better, all we’ve got to go on is our gut, and that’s a wild, terrifying, wonderful thing. Sometimes, it can only talk with a song.
*A previous version of this story incorrectly claimed that the Smiths’ “Please, Please, Please Let Me Get What I Want” did not play in Pretty in Pink. In fact, it plays briefly over one of Duckie’s many sadboy moments in the film. We regret the error.