What do Cruel Intentions, American Pie, 10 Things I Hate About You, She’s All That, Never Been Kissed, Varsity Blues, Drive Me Crazy, Election, The Virgin Suicides, Drop Dead Gorgeous, and Jawbreaker have in common? Aside from representing much of the canon of newly classic teen movies, every single one of these films came out 15 years ago, in 1999. What was it about that year, specifically, that led to this cinematic gold rush?

The influx of teen movies at the end of the millennium was more than just a product of a national obsession with Sarah Michelle Gellar and Kirsten Dunst, both of whom were arguably at the peaks of their careers at the time. The Golden Year of Teen Movies, as we might call it, marked a convergence of technology, population growth, economic prosperity, and a change in the cultural conversation about teenagers as a whole. I’d even go so far as to say 1999 was when the concept of “The Teenager” as we understand it in the 21st century was created. It’s a fascinating story seeped in money and power shifts as teens became an important and distinct demographic in their own right — so let’s open up the shoebox time capsule and explore.

First of all, there were more teenagers in the United States than there had ever been in the history of the country. According to a 1999 Boston Globe article titled “Whatever, Teenagers’ Tastes Are, Like, You Know, Setting the Agenda for the Rest of Us,” 30.9 million Americans were between ages 12 and 19. These teens were the offspring of the baby boomers, their label fluctuating between “Gen Y” and “the echo boom” (which sounds way cooler than “millennial”).

Not only had teens descended upon America in droves, but they were a strange new species — a species that confused their parents, who spoiled and coddled them, but also felt more removed from their children than ever. The strangeness of the modern teen to adults is evident from that headline, one of dozens from 1998-2000 that cheekily mimicked “teenspeak” by including “like” in the title. To read through them in succession feels a bit like when someone makes too many “casual” jokes about the same thing, and you realize that thing is making them feel desperately insecure. The grown-ups were freaked out.

American Pie

Language aside — teens have always had their own slang, after all — most of this strangeness arose from money and technology. Spending both their parents’ money and their own, teens had more discretionary cash than ever before, with the average teen dropping $99 per week in 1999: $28 from their parents and $71 of their own money, according to Teenage Research Unlimited. Publishers churned out teen versions of grown-up magazines, like CosmoGIRL! and Teen People. Britney Spears, Christina Aguilera, Brandy, ‘N SYNC, and the Backstreet Boys dominated the Billboard charts. Gap and Abercrombie & Fitch saw their stock prices skyrocket.

Pre-PayPal startups like RocketCash.com searched for ways to help teens spend all that cash online without having to ask for parents’ credit cards (or using their own, which 1 in 9 teens had). Companies like DuPont hired cool teens as marketing consultants. Networks scrambled so frantically to cast teen TV pilots (because of interest, but more importantly, advertising dollars) that there was a shortage of young actors, and agents had to resort to open casting calls. Told you Sarah Michelle Gellar and pals were busy.

Quantum leaps in technology were dividing parents and their children even further. For the first time, teens were getting their own cell phones and pagers, able to socialize with each other without worrying that Dad was listening in on the receiver downstairs. According to a now-hilarious New York Times piece from 2000, “Many of the teenagers interviewed said they kept their parents at arm’s reach by doing things like turning off their cell phones or telling white lies about dead batteries.” The horror!

The Internet, too, was a source of hand-wringing and mystery for parents, while teens were forging their own online communities and carving out new identities for themselves among various peer groups. With all the hanging out and shopping, adults constantly referred to the web as a “virtual mall.” It was clear that teens were searching for both their own space and their own voices.

The Virgin Suicides

And some teens helped others find these voices. In response to Mary Pipher’s 1994 bestseller Reviving Ophelia, a psychology book about the plight of adolescent girls, 18-year-old Sara Shandler compiled a book of essays written by teenage girls called Ophelia Speaks, in 1999. The New York Times asked Shandler why the pressures of growing up were different for her generation than those past, and she addressed points in her answer that are still relevant today:

To say just one thing oversimplifies it. But I could point to a few things like the media representation of women. We equate thinness with success. There’s also the pressure to have a good job when you finish school and be successful. The feminist movement came with some incredible benefits, but it has its downfalls as well. I think there’s more pressure to be a mini-adult from the time we’re very young.

The economy isn’t quite as booming as it was at the turn of the millennium, but these concerns are still relevant for teens today: the pressure to be successful, our struggles with media representations, and the strange gray area of this time after the feminist movement but before true equality. The differences between past and present youth that people noticed in 1999 still stand — so this “echo boom” generation, which bleeds into today’s “millennials,” represents the birth of The Teenager as we understand it in 2014.

The complexity of this new teen is reflected in the scattered tones of their cinematic tastes. What’s interesting about the spread of teen films listed above is that they don’t fall into one particular genre. She’s All That, American Pie, and even the feminist Taming of the Shrew remake 10 Things I Hate About You are relatively standard teen fare — they’re lighthearted and a bit raunchy, but essentially just love stories. But films like Cruel Intentions and The Virgin Suicides, classics though they might be, are dark: no matter how much you enjoy watching them, you can’t ignore the prominent theme of teen death that lingers above them in a gray fog.

Jawbreaker

Occupying a middle space between dark and light are the black comedies Jawbreaker and Drop Dead Gorgeous, self-aware critiques of the fatality of yearning to be popular. These satires owe a lot to their late-’80s predecessors like Heathers, Better Off Dead, and Pump Up the Volume. Jawbreaker specifically is almost a next-generation Heathers remake, but redone with slick and expensive production to appeal to the new teens. What makes the ’90s movies different though, is that their messages weren’t quite, “Being popular is bad,” but more like, “Being yourself will make you popular among good people.”

The ’80s were about standing out, but the ’90s films were about fitting in while staying true to yourself. Veronica in Heathers eventually left the popular crowd to escape its toxicity, while the victim in Jawbreaker, Liz, was an ideal teen: the one popular girl who was actually nice. This shift in movie morals reflects the shift in ’90s teens’ actual values. Members of the echo boom were doing fewer drugs, having less sex, and were less interested in rebellion and politics than both their parents’ generation and Generation X before them. They were more concerned with conforming (remember that Abercrombie stock surge?) than with finding their own way.

We can recognize this template (be nice, don’t rock the boat, have friends) in later movies — at the end of 2004’s Mean Girls, the Plastics may have disbanded, but they all happily find mini-cliques to give them that sense of belonging. This idea of mini-cliques or smaller, niche friend groups mirrors both the splintering of the 1999 teen movies into mini-genres and the various virtual “clubs” the Internet provides, both then and now.

10 Things I Hate About You

A big part of the reason why these Golden Year movies so skillfully capture the teen mood of their era is that the people writing and directing them were young, too — in their late 20s or early 30s, the generation right between the boomers and the echo boom. American Pie was written by Adam Herz, age 27; 10 Things I Hate About You was written by Kirsten Smith, age 29, and Karen McCullah Lutz, age 33; R. Lee Flemming wrote She’s All That at 29; Abby Kohn and Marc Silverstein wrote Never Been Kissed in their 20s; Rob Thomas wrote Drive Me Crazy at 34 (and, later, Veronica Mars and 90210, because he’s always understood teens); Darren Stein wrote and directed Jawbreaker at 28; Sofia Coppola directed The Virgin Suicides at 28. This generation not only understood the thoughts and desires of the teenage years they’d recently left, but had the power to actually create these films, and the ability to communicate with the generation above them, who presumably provided the funding.

We owe the vibrant teen culture of today to these financially secure non-rebels, the trail-blazing mall rats of 1999, and also to the grown-ups who figured out how to grab a hold of that money. And of course, let’s wish a happy 15th birthday to all these great films, which, it’s worth noting, are now in their teenage years as well.