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

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