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

President game show 73rd Emmy Awards young adult sports movie The Witch Tubi joker blockbuster Horror Mindy Kaling WGN Schedule Rocketman video Amazon Studios space Hallmark OWN live action franchise VH1 Avengers kong king kong AMC screenings Sundance documentaries stand-up comedy blockbusters rt labs critics edition Grammys Classic Film Mudbound BBC One science fiction Set visit jamie lee curtis finale historical drama Red Carpet ABC Adult Swim Oscars FOX Heroines The Arrangement Nominations suspense deadpool CBS All Access NYCC justice league 2015 spain Legendary Captain marvel cops PaleyFest Chernobyl Family mob Acorn TV Pride Month Universal Anna Paquin Fox Searchlight DC Comics comic book movies Disney reboot spanish language stoner BAFTA asian-american child's play christmas movies TNT art house based on movie cartoon Neflix Netflix American Society of Cinematographers Disney Plus E3 Pacific Islander animated Women's History Month CW Seed natural history Superheroes ABC Family archives chucky telelvision book adaptation television reviews The Walking Dead Black Mirror crime drama Paramount Plus comiccon black breaking bad X-Men italian witnail Cosplay Comedy Central ViacomCBS Television Academy satire crime HBO Max 2018 scary streaming Lifetime Logo Baby Yoda richard e. Grant news Mystery GLAAD zombie APB IFC Sci-Fi Drama sopranos psycho dceu Elton John Calendar Fall TV spider-verse Marvel Television toronto Awards dogs NBA Sundance Now 21st Century Fox movies Emmy Nominations Hulu thriller indiana jones Awards Tour TV movies women MTV ITV romantic comedy Binge Guide sitcom political drama nfl rt archives Epix films Countdown royal family unscripted rt labs what to watch FX on Hulu anime TCA 2017 live event 20th Century Fox japanese Comics on TV Biopics The Purge Britbox target Western theme song Wes Anderson Holiday Crunchyroll Black History Month WarnerMedia hollywood Trophy Talk crossover Esquire Shondaland TCA Winter 2020 comic rotten canceled TV shows documentary marvel comics hidden camera Rom-Com boxoffice BET Awards halloween tv slashers sequel romance batman Pixar DC streaming service Musicals spanish 2020 teaser Creative Arts Emmys zombies 45 Disney streaming service Spring TV facebook australia Exclusive Video zero dark thirty comics jurassic park cinemax dc TruTV disaster cancelled Year in Review 2016 Martial Arts 007 serial killer renewed TV shows Image Comics El Rey worst movies Country Comic-Con@Home 2021 hist razzies Ellie Kemper Star Trek MCU emmy awards Valentine's Day Endgame HBO Go Hear Us Out period drama politics Sony Pictures History Hallmark Christmas movies ESPN Best and Worst TCA Awards basketball talk show Video Games biography free movies anthology Emmys green book Academy Awards festivals Nat Geo Masterpiece Alien hispanic Music olympics composers Brie Larson toy story docudrama Amazon heist movie critics Apple TV+ First Look kaiju Box Office adaptation Infographic spider-man Apple Winter TV Fox News Toys Spike know your critic Peacock Universal Pictures Ovation TCM dark strong female leads Turner Crackle high school war mission: impossible Sundance TV National Geographic travel Summer cults Interview wonder woman Action festival Netflix Christmas movies dreamworks book 2017 diversity Film Instagram Live video on demand Polls and Games doctor who Turner Classic Movies GIFs 24 frames Marathons 1990s Tomatazos TLC 90s Funimation children's TV Columbia Pictures saw San Diego Comic-Con Mary poppins critic resources ABC Signature golden globe awards Mary Tyler Moore Travel Channel die hard Discovery Channel james bond The CW ID Freeform universal monsters BET quibi Starz Dark Horse Comics Holidays independent Paramount rom-coms action-comedy indie TBS Amazon Prime foreign genre biopic crime thriller comic books SundanceTV dramedy vs. Writers Guild of America Unbreakable Kimmy Schmidt 71st Emmy Awards Ghostbusters dragons mockumentary Teen adenture robots new zealand CNN cancelled TV shows USA Network miniseries parents Trailer First Reviews A&E ratings social media werewolf sequels latino superhero YouTube Red international monster movies Star Wars IFC Films classics Stephen King AMC Plus fresh Chilling Adventures of Sabrina Cartoon Network Film Festival ghosts streaming movies YouTube Premium casting Christmas all-time 2019 FXX BBC America scene in color new york boxing sag awards comedies Amazon Prime Video Lionsgate Super Bowl gangster psychological thriller Kids & Family Reality concert debate aliens Comedy Comic Book RT History VICE true crime vampires cancelled TV series best singing competition Reality Competition FX PBS aapi 4/20 Election 2021 mcc See It Skip It IMDb TV superman black comedy harry potter Fantasy Marvel Studios TIFF Broadway cancelled television godzilla VOD Superheroe NBC CMT Opinion E! series new star wars movies 93rd Oscars TV One The Walt Disney Company Tumblr versus OneApp football slasher Quiz YouTube Vudu japan DGA Disney+ Disney Plus Sneak Peek a nightmare on elm street Syfy Extras Pop canceled hispanic heritage month marvel cinematic universe 78th Annual Golden Globe Awards Podcast tv talk twilight Warner Bros. Tarantino Nickelodeon Spectrum Originals transformers Arrowverse adventure golden globes Musical Pop TV directors remakes screen actors guild obituary GoT Lifetime Christmas movies halloween Apple TV Plus Winners Cannes fast and furious LGBTQ Lucasfilm CBS discovery MSNBC popular laika scorecard spinoff BBC Bravo HBO Television Critics Association SXSW PlayStation spy thriller dexter Rocky supernatural Animation Food Network trailers DC Universe 72 Emmy Awards game of thrones medical drama king arthur RT21 Photos Song of Ice and Fire Paramount Network Pet Sematary prank Thanksgiving criterion feel good venice SDCC DirecTV cooking nbcuniversal pirates of the caribbean TV renewals legend elevated horror police drama Showtime Premiere Dates 99% comic book movie cats LGBT TV Land Character Guide Trivia Disney Channel posters revenge award winner blaxploitation mutant Pirates The Academy Walt Disney Pictures cars TCA A24 docuseries french Rock technology Marvel nature binge Shudder south america name the review worst kids Tokyo Olympics USA New York Comic Con rotten movies we love Watching Series Mary Poppins Returns lord of the rings YA stop motion TV Certified Fresh scary movies