Why 1999 Was The Ultimate Year for Teen Movies

10 Things I Hate About You turns 20 this year. So do American Pie, Cruel Intentions, and so many more.

by | March 31, 2019 | Comments

Touchstone courtesy Everett Collection
(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

Paramount courtesy Everett Collection
(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

Paramount courtesy Everett Collection
(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 RingEighth 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 $13 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

Universal Pictures courtesy Everett Collection
(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 – JawbreakerElection — 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 NowDopeThe Edge of SeventeenSing 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.

Tag Cloud

Interview San Diego Comic-Con Podcast cooking joker what to watch reboot directors DC streaming service Amazon ITV dragons indiana jones Creative Arts Emmys child's play Chernobyl History cops National Geographic Comedy Central Disney streaming service teaser Elton John TV renewals Holiday Film Festival Pop Drama transformers IFC Films versus Vudu Reality A&E Pet Sematary The Walking Dead OneApp animated concert Nominations Rock Photos The Witch comedies GoT 2019 crime Christmas a nightmare on elm street APB IFC Marvel Studios Sci-Fi Baby Yoda The Arrangement Fantasy FXX mockumentary reviews Certified Fresh elevated horror spider-man canceled TV shows Crunchyroll Summer golden globes Superheroes revenge SXSW TV Land Star Trek zombies Western binge spy thriller green book Chilling Adventures of Sabrina biography 2016 Star Wars Superheroe anime documentaries Avengers CNN Acorn TV book Pride Month YouTube Premium President TV DC Universe serial killer casting vampires Mudbound sag awards Disney Plus parents Marathons Premiere Dates quibi sports Super Bowl dramedy game show Oscars Black History Month independent travel Freeform First Look Polls and Games Martial Arts dceu spinoff Sundance TV Endgame natural history Fox News Holidays rotten movies we love Adult Swim Thanksgiving Mary poppins 20th Century Fox psychological thriller Pirates south america 4/20 zombie Opinion Universal Masterpiece Rom-Com mutant Dark Horse Comics tv talk BET Awards RT21 cancelled TV series twilight TBS Cosplay Box Office singing competition Election Emmys Tomatazos Spike dark Spectrum Originals Rocketman politics TruTV The CW MTV Action Turner Logo PlayStation breaking bad Comedy dc cancelled TV shows CBS All Access die hard science fiction Tarantino romance Columbia Pictures screenings discovery Ovation cinemax Funimation television documentary Warner Bros. Apple TV+ SDCC MCU Cartoon Network FOX Country Ghostbusters political drama Infographic 2018 BET CW Seed award winner Hallmark Christmas movies Disney Channel psycho Toys A24 Grammys Sony Pictures Watching Series indie PBS TCM Lifetime Christmas movies OWN Writers Guild of America Travel Channel NYCC VOD game of thrones Awards Mystery Ellie Kemper satire diversity canceled Classic Film technology Video Games Calendar unscripted renewed TV shows Set visit aliens doctor who 45 TCA robots Nickelodeon Amazon Studios Shudder movies Nat Geo Apple boxoffice police drama Bravo chucky jamie lee curtis New York Comic Con FX on Hulu Countdown E3 Academy Awards dogs Quiz Peacock adaptation 2017 disaster Sundance adventure festivals YA Song of Ice and Fire zero dark thirty series criterion facebook Kids & Family Pixar FX HBO name the review best Rocky 24 frames hispanic Extras Syfy Heroines screen actors guild ghosts LGBT Disney+ Disney Plus streaming WarnerMedia DirecTV The Purge First Reviews blockbuster comiccon true crime Crackle Music MSNBC Epix universal monsters based on movie 21st Century Fox all-time Binge Guide Winners supernatural blaxploitation Animation free movies Disney Best and Worst Hear Us Out Mindy Kaling HBO Max Netflix Christmas movies halloween docudrama BBC America films Captain marvel BAFTA stoner Horror spain CBS talk show comic Brie Larson Valentine's Day romantic comedy Amazon Prime Video AMC comics mission: impossible harry potter theme song TCA Winter 2020 RT History NBC Trivia hist stand-up comedy DGA video on demand cults Discovery Channel franchise TIFF El Rey cartoon Women's History Month movie Emmy Nominations social media children's TV ABC Family Spring TV Character Guide sequel historical drama cancelled Hallmark Stephen King medical drama cats GLAAD critics kids crime drama strong female leads LGBTQ latino composers American Society of Cinematographers Netflix toy story asian-american BBC PaleyFest werewolf Biopics TLC TNT Reality Competition Tubi Lucasfilm batman Comic Book cars 007 Mary Tyler Moore Amazon Prime WGN Family nature Lifetime witnail Britbox period drama TCA 2017 Walt Disney Pictures sitcom 71st Emmy Awards SundanceTV video miniseries richard e. Grant USA Network GIFs Schedule Sneak Peek E! CMT Sundance Now 2020 Mary Poppins Returns Black Mirror Musical Awards Tour foreign Turner Classic Movies Tumblr Teen ABC ratings BBC One news DC Comics Marvel Television Anna Paquin Showtime Year in Review Pop TV Marvel crime thriller slashers anthology ESPN HBO Go space See It Skip It thriller Paramount Network Esquire Television Academy scary movies cancelled television YouTube 2015 Unbreakable Kimmy Schmidt X-Men Paramount Cannes Arrowverse Fall TV crossover Apple TV Plus Red Carpet christmas movies finale Musicals Trailer YouTube Red Hulu war VICE Starz spanish language USA VH1 Film justice league Lionsgate Trophy Talk Comics on TV Shondaland Winter TV Food Network