Pretty in Pink turns thirty this year. Written by John Hughes and directed by Howard Deutch, the film stars Molly Ringwald, Andrew McCarthy, John Cryer, James Spader, Annie Potts, and Harry Dean Stanton. It would be an understatement to say that if you were of a certain age in the late 1980s and early 1990s, and went to a school like the one in the film, this was one of the defining films in your young life. The movie imprinted on people who grew up watching it, in the way that can only happen when you’re a teenager and movies aren’t merely enjoyable to you but are instead your life reflected back at you onscreen. I was only a kid when Pretty in Pink came out so I likely didn’t see it until a couple of years later, probably in 1989 or 1990, once I had entered high school. It became an instant favorite. Kids in my school knew the lines by heart and would quote them often—I particularly remember loving Duckie’s line, “His name is Blane? Oh! That’s a major appliance, that’s not a name!” This was occurring in high schools across America. The movie still resonates with viewers today, both those that grew up with it and those that discovered it decades later.. The clothing and hair styles may be rooted in the ’80s, but the personal details about what it’s like to be in high school and feel isolated and separated from the “cool kids” never goes out of style.

Most of us can find a character, or characters in some cases, to relate to in Pretty in Pink. Andie (Ringwald) gave voice to what a lot of us were feeling at that age—her social position in school was predetermined from the onset and she wasn’t allowed to change status during her remaining years in school. That’s usually the way it goes in high school; you’re labeled, or in certain cases not labeled at all (I’m not sure which is worse), and from that point on you will remain in whichever group you were assigned. Are you a slacker? A burnout? A popular kid? An athlete? A nerd? A nobody? In high school, there is very little movement between these social groups. I was a loner at heart, an only child like Andie who had a vivid imagination, typical social awkwardness for that age, and a sarcastic sense of humor. I spent more time living in my head than in my daily life for a while. And like Andie, I often felt like an outsider, sometimes even within groups of friends. Also like Andie, I didn’t feel like I understood the hierarchy, or why it had to be that way, and so this confusion only compounded feeling like an outsider. In Andie’s case, she’s an actual outsider, living literally on the other side of the tracks in town, a dividing line separating the rich and cool kids from the middle class and poor losers. And most of us can relate to this feeling of being an outcast at some points in our lives, whether the tracks we live beyond are literal or figurative.

Andie’s feelings toward Blane (McCarthy) provide the film’s central conflict and drive the plot. They flirt awkwardly at first and she’s amazed that a rich kid like Blane would notice her let alone like her. Once they begin to date, it becomes clear to Andie that she’s not of his world and never will be, and Blane also struggles with this because of external pressure from his friend Steff (Spader, in ultimate creep mode), who denigrates Andie any chance he can get. She rejected him earlier in the movie—rightly so, he’s an absolute jerk—so his motives aren’t entirely pure. Andie and Blane break up after she’d planned to attend the prom with him. This leads to her making the difficult decision to go alone, because as she tells her father, “I just want them to know that they didn’t break me.” It’s a huge moment in the movie, an empowering one for all the kids watching who were like Andie. Blane isn’t heartless though, and the film does a nice job of subverting our expectations and assumptions about rich, popular kids through his character. He’s clearly a nice guy at heart, albeit too easily influenced by unscrupulous friends like Steff. That’s standard for all teens, no matter their social positions. Like Andie, Blane’s also stuck in his own social standing, and while his is the one everyone wants to be in, he’s still not happy most of the time. He simply wants to be with Andie, high school rules be damned.

Duckie (Cryer) is Andie’s best friend and spends the movie pining for Andie, mostly hilariously but also at times pathetically. Duckie is the character a lot of us related to at the time. Spoilers for a thirty year old movie: he doesn’t wind up with Andie romantically by film’s end. This upset a lot of viewers then because it felt like it sent the wrong message by having Andy choose Blane, the kid who already had everything. But it’s clear that Duckie and Andie were just friends—best friends, but not more than that. No matter how hard Duckie pushed, Andie was never going to feel the same way towards him. And while Duckie was a hero to a lot of us, his actions in the movie are often times worse than those of the rick kids. He tells Andie he’s totally cool with just being friends and then spends the entire movie being upset when she won’t be more than friends with him. It’s something a lot of us experienced, liking someone who didn’t like us that way but wanted to be friends. Most of us agreed to be friends but then spent our time both still pining away and being frustrated with the object of our affection for just not getting that we belonged together! It’s a special kind of obliviousness associated with youth. Hopefully we outgrow it, and most of us do. Duckie in fact sets the example for all of the other Duckies in the world by growing enough as a person and finally listening, really listening, to Andie. At the prom he even does what a best friend should do by encouraging her to go after Blane because it’s clear she wants to be with him. I would like to say I had that sort of maturity in high school, but I’m pretty sure that would be a lie, Still, Duckie’s example resonated with a lot of us over the years, in meaningful ways.

At one point, Duckie overhears Steff telling Blane that Andie “was, is, and always will be nada.” Duckie waits there in the hallway for Steff. They stare each other down. “This is my moment,” you can almost imagine Duckie telling himself. Steff represents everything Duckie hates about high school, and he’s fed up enough now to finally express his anger with his fists. Duckie tackles Steff and they get into a realistically messy fight in the hallway before a teacher finally breaks it up. It’s an incredible scene between the actors, with Cryer especially making us believe in his character’s frustration and total loss of control. After the fight is broken up he runs down the hall and in midstride leaps up and tears down the school dance banner hanging overhead. His destruction of the sign is clearly a metaphor for how he feels about high school. Sometimes you need to tear things down in order to move past them. It’s an iconic scene, one that’s been included in any number of movie montages over the years. Its appeal lies in the fact that most of us never vent our pent-up aggression on our high school oppressors, as much as we might want to. Instead, we stuff it all inside and become snarky and cynical, partly as a way to deflect those feelings. We can look back on it later and laugh about it, because we have enough distance to find it amusing. But when you’re just a kid, seeing Duckie do what we all wanted to do was huge.

The film doesn’t focus solely on Andie’s time in school, but instead also delves into her life outside of that hellhole. In doing so, it opens up her world to us and shows us just how mature she is for her years, due to her life circumstances. Her mother left her and her dad Jack (Stanton) years ago and he’s held out hope ever since that she would return to them. Andie knows that’s not happening. In many ways, Andie is the adult in her household, with her dad taking on the role of the unrealistic and erratic kid at times. He struggles to find employment. He’s clearly suffering from full-blown depression. Yet through his troubles he’s still loving and supportive towards Andie. He simply loves his daughter, no strings attached. The sun rises and sets with her, in his eyes. He’s one of the more supportive, if flawed, parents or adults from teen films of that era. Andie’s friend at the record shop, Iona (Potts) is another example of how not all adults are out to ruin teenagers’ lives. Iona also supports Andie and encourages and fosters her creativity as well. Her record store provides a sanctuary for Andie from the difficulties at home and at school. There, she can truly be herself and let her freak flag fly with the eccentric Iona. The characters of Jack and Iona are two more reasons why Pretty in Pink is so special. It dares to portray the two main adults in the film as overwhelmingly supportive of Andie, breaking with the stereotype of the evil adult that was used in so many films of the time.

Several people during my high school and college years told me I looked like Andrew McCarthy. The resemblance then was pretty strong, and even now when my hair’s longer and I wear sunglasses on top of my head and smile just right, I still look like a bit like Pretty in Pink McCarthy. I tell this story to convey just how omnipresent this movie was in our lives back then, and whenever this resemblance would be mentioned over the years it would be another reminder of the impact it had on my generation. It became a part of us, and extremely personal to many of us in ways that only certain movies can be. The music in the film was a soundtrack to our lives. That’s a cliché, but only because it’s true. The character types were instantly recognizable to us, allowing us to see ourselves in them in important ways. There are so many teen movies from that era that were insightful about what it felt like to be a teenager. Several were just as good as Pretty in Pink, but none were better at portraying how high school caste systems unfairly marginalize too many kids. That’s why it remains powerful to viewers thirty years on.