(Photo by Touchstone courtesy Everett Collection)Filmmakers like Cameron Crowe, John Hughes, and Bob Clark may make us think the 1980s were the true renaissance of movies made for and about teens, but let’s not discount the 1990s – specifically one year in particular: 1999.Depending on your definition of teen movie, there were up to 19 films in this genre released that year, according to Phillip Iscove, the television writer and co-host of the all-things-1999-movies podcast, Podcast Like It’s 1999. Even more important, Iscove says, is that teen rom-coms like 10 Things I Hate About You and She s All That, black comedies like Jawbreaker and Cruel Intentions, and coming-of-age films like The Wood and American Pie still resonate with those who grew up in and around that era because “there’s a universality that they’re trying to hit.”But why this year in particular? Surprisingly, it’s not just because one of them featured Heath Ledger singing in the high school bleachers.The Clueless and Romeo + Juliet Effect(Photo by Paramount courtesy Everett Collection)Before we dive into the year of 1999, let’s act like Alicia Silverstone’s Cher Horowitz from Clueless and totally pause at the mid-‘90s. Writer-director Amy Heckerling adapted that 1996 film from Jane Austen’s classic novel, Emma, replacing Regency-era British aristocracy with a posh Beverly Hills high school while star Silverstone kicked the dumb blonde trope out with last season’s fashions. A year before this, Baz Lurhmann’s flashy Romeo + Juliet set the Bard’s famous play about star-crossed teen lovers in a gritty, steamy beach city and made male lead Leonardo DiCaprio a teen heartthrob (his female counterpart, Claire Danes, was already known to younger audiences thanks to her cult TV show, My So-Called Life).So it shouldn’t be a surprise that, by the time greenlights, casting, and production turnarounds were through, we’d land in 1999 with 10 Things I Hate About You, an adaptation of Shakespeare’s marital comedy The Taming of the Shrew about elaborate scheming to marry off one daughter in order to gain access to another; She’s All That, which is rooted in George Bernard Shaw’s Pygmalion, a play about teaching a lowly flower salesgirl how to pass in high society; and Cruel Intentions, which is based on Les Liaisons dangereuses, Pierre Choderlos de Laclos’s novel about bored socialites who break hearts for sport.“Clueless was proof-of-concept that there’s an audience [for modern adaptations of classic works] if it’s done well,” says Neil Landau, a screenwriter and professor at UCLA School of Theater, Film and Television. “Adults who greenlight movies love when it’s source material. It doesn’t feel as frivolous. I think the young people see them because of the canon and the things you study in high school.”Plus, he says, these works were in the public domain and therefore cheap to get licensing rights.Independents Studios + DVD Sales = Boffo Profits(Photo by Paramount courtesy Everett Collection)It’s also important to remember what was going on in the industry itself at that time. She’s All That was distributed by Miramax when it still was the hip younger sibling brought in to spice up Disney. 10 Things I Hate About You was distributed by Touchstone Pictures, which is also part of Disney. American Pie was produced by Summit when it was still considered an independent studio. Then there’s MTV Films, which, Iscove reminds us, had an ambitious slate in 1999 that included Varsity Blues, Election, 200 Cigarettes, and The Wood – all movies for or about teens and young adults that were released in July or earlier of that year. He says, nowadays, companies like Annapurna Pictures (Everybody Wants Some!!) and A24 (The Bling Ring, Eighth Grade) excel at distributing and producing these films, but it’s not all they do.Part of this is because we’ve since changed how we look for these types of movies. Tim Gray, the senior vice president and awards editor at Variety, says his trade magazine wrote in 1998 that “DVD players were expected to hit 1.4 million in 1999.” He says that number may sound like small potatoes, but it was a strong indicator that the public was willing to commit to a new technology – especially since he says Variety also ran an advertisement around that time saying that “it would be a billion industry within a decade.” Since teen movies were still cheap to make, Gray says that “indie companies were emboldened by that idea” of DVD viewership the way that video cassette players in the 1980s made Hollywood realize that there was still business to be had once a film left theaters.Iscove argues that the desire for teens to see themselves on screen hasn’t changed – just how they find them may have evolved. We all know what “Netflix and chill” is code for, but think of the success of films like To All The Boys I’ve Loved Before and Alex Strangelove and realize that the kids may want to watch something on streaming channels too.White Male Humor Still Dominated(Photo by Universal Pictures courtesy Everett Collection)The late ‘90s was still a time when white, male, heteronormative bro-culture dominated, especially since the (mostly male) development executives who were green-lighting these films had themselves been raised on now-questionable films like Porky’s and Risky Business. While there are exceptions – Jawbreaker, Election this was an era where teen boys were straight, cis-gender, and supposed to treat sex like a conquest (see: Cruel Intentions and American Pie) and where teen girls were supposed to be OK with prettying themselves up and potentially dumbing themselves down in the name of popularity (see: 10 Things I Hate About You and She’s All That). Oftentimes, these kids were white, suburban, and entitled. When the idea of sexual assault is brought up, such as Julia Stiles’ Katarina’s reveal toward the end of 10 Things, it’s done in an almost blink-and-you’ll-miss-it way.“It was the beginning of the ending of an era,” says UCLA’s Landau of this period when “virginity is a rite of passage for boys. For girls, it was filled with shame and stigma.” He says this only influenced mainstream views, as chances are girls and young women were going with boys in their age brackets to see these movies either in groups or on dates.However, these norms have evolved considerably since 1999. Director Kay Cannon’s summer 2018 hit Blockers threw the double-standard that girls can’t own their own sexuality in our faces. Some of the biggest successes to come out of the recent South by Southwest film festival were Booksmart and Snatchers, which mock the finger-wagging trope of “good girls don’t do that.” As for films about boys and sex? Another hit from SXSW was Good Boys, which still has rauchy humor but – as the trailer reminds us – features boys from a much more innocent age.We may never get another year as robust with movies that cater specifically to the teen audience as we did in 1999, and we may never again get teen movies quite like the ones we saw that year. But thanks to films like Blockers, like Eighth Grade, like The Spectacular Now, Dope, The Edge of Seventeen, Sing Street, and Lady Bird, we can rest assured that the genre is in good hands, and the adolescents of today won t lack for entertainment that speaks to them on a personal level too.Check out our list of every 1999 teen movie ranked here. What were your favorites? Tell us in the comments!Like this? Subscribe to our newsletter and get more features, news, and guides in your inbox every week.