News

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

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