1999 was quite the year for film. The Sixth Sense established M. Night Shyamalan as Hollywood’s premier suspense man with an affinity for surprise endings. Hilary Swank turned heads for her performance as a transgender man in Boys Don’t Cry, as did Angelina Jolie for her portrayal of a rebellious sociopath in Girl, Interrupted. Phil Collins won an Oscar and Golden Globe for Best Original Song after creating one of the most memorable soundtracks of all-time for Disney’s Tarzan, and American Beauty received the most Academy Award nominations that year. But 1999 was also a seminal year for the teen comedy film—with two exceptional comedies in particular celebrating their twentieth anniversaries as timeless classics.

If anything, a majority of teen rom-coms released in 1999 had something in common: they set a trend for reimagining classics of literature as youth comedy films (not to mention Clueless had set the gold standard for the trend four years earlier in 1995, which was actually a retelling of Jane Austen’s Emma). She’s All That, starring Freddie Prinze, Jr. and Rachael Leigh Cook, was a ‘90s teen retelling of Bernard Shaw’s play Pygmalion and 1964’s My Fair Lady. Cruel Intentions, featuring Sarah Michelle Gellar, Reese Witherspoon, Selma Blair, and Ryan Phillippe, reimagined the French novel Dangerous Liaisons—originally from 1782—as a ‘90s precursor to Gossip Girl set amongst wealthy New York City high school students instead of 18th-century France. Conversely, there was also Dick—a comical retelling of the real-life Watergate scandal starring Kirsten Dunst and Michelle Williams, as well as the notoriously misogynistic but still somehow endearingly beloved American Pie, whose plot historically speaks for itself. Amidst this crowded backdrop of comedy films targeted at teens and youth, 10 Things I Hate About You—a loose modernization of Shakespeare’s The Taming of the Shrew—arrived and changed the landscape forever.

10 Things I Hate About You introduced us to a lot of faces. It was a breakthrough film for Julia Stiles and Joseph Gordon-Levitt, and made Heath Ledger a reluctant worldwide star. But the film also introduced us to the one and only Kat Stratford, portrayed by Stiles. In a nutshell, Kat is an unabashed misfit who refuses to fit in at her high school or play by the standards set by anyone else but herself. Her younger sister Bianca (Larisa Oleynik) is the complete opposite—a charming and perky queen bee who is admired and desired by half of their school’s male population. The problem? Their strict father will not allow Bianca to date until Kat does, presenting a large conundrum considering Kat refuses to conform or play by the rules, leading her to appear undesirable at best to the “unwashed miscreants” at her school. In a turn of events, Cameron (Gordon-Levitt)—who wants to date Bianca—enlists the help of the mysterious and feared burnout Patrick Verona (Ledger) to take out Kat so he can ask out Bianca. As most 20th-century rom-coms go, pandemonium ensues and betrayal is in the air—but it resolves itself neatly enough for a happy ending. The difference here, however, is that someone like Kat Stratford had gone completely unrepresented until 10 Things I Hate About You hit theatres in 1999, and she completely reinvented the mold for female misfits.

Julia Stiles as Kat and Larisa Oleynik as Bianca in 10 Things I Hate About You, 1999 (Photo: Buena Vista Pictures)

Misfit girls weren’t unheard of when 10 Things I Hate About You came out, but they were still far from normalized or taken as seriously as head cheerleaders or perky it-girls. Allison Reynolds (Ally Sheedy) burst onto the screen with her unhidden eccentricities and weirdness in The Breakfast Club, and one could even say Andie Walsh (Molly Ringwald) from Pretty in Pink was a misfit protagonist for her supposedly unusual ambitions, embraced independence, and less fortunate upbringing, but she was far from breaking the mold as far as unconventional visions of women go. Even Laney Boggs (Rachael Leigh Cook) from She’s All That wasn’t much of a misfit protagonist since she was apparently always beautiful under her geeky glasses and ugly overalls—it’s hard to truly frame a female character as a misfit when the given underlying implication is that they never really had to be misfits in the first place, combined with the fact that the “happy ending” in these tales is finally fitting in, whatever that means, or worse; being taught how to fit in. But 10 Things I Hate About You did what the aforementioned films could not: they made the female misfit cool. Unlike Allison Reynolds or Laney Boggs, Kat Stratford never needed someone to notice her or bring her out of her shell, simply because she didn’t care. Kat exuded a level of primal independence and self-confidence that is still scarcely presented to audiences, let alone women, in such an abrasive and unapologetic way. Kat didn’t care what people thought. She could call Ernest Hemingway an alcoholic misogynist in her English class without flinching, and could smash the car of her school’s cocky pretty boy when he wouldn’t move out of her way. She stood out not only because she didn’t feel the need to fit in, but because she was confident enough in herself to not care about other people’s perceptions of her. For a teenage girl to be portrayed with such power to summon the strength inside herself outside of other people’s expectations is nothing short of revolutionary. Most teenagers would be too self-conscious to be such an open outcast, but Kat Stratford led by example. She threw everyone’s expectations of her out the window in favor of who she wanted to be. “I don’t like to do what people expect,” she says. “Why should I live up to other people’s expectations instead of my own?” Kat didn’t even have to sacrifice her rebellious, grunge rock-loving exterior to be taken seriously by a male counterpart, something that is practically ingrained in most other female misfit narratives. Even twenty years later, she is still so refreshing as a young female character who was not only allowed to be an angry girl but as someone who refused to let anyone get in her way. She helped bring female nonconformists into the mainstream and redefine the rules for them, giving women more of a platform to be people with stories rather than a vessel to further a man’s story. Kat’s impact on female narratives was evident by the time Legally Blonde followed in 2001, and certainly helped create other misfit characters like Janis Ian (Lizzy Caplan) in Mean Girls or Juno MacGuff (Ellen Page) in Juno.

Drew Barrymore as Josie Geller and Michael Vartan as Sam Coulson in Never Been Kissed, 1999 (Photo: 20th Century Fox)

Much like the female-written and female-driven nature of 10 Things I Hate About You, 1999 brought us another groundbreaking and, in many ways, revolutionary romantic comedy film: Never Been Kissed, starring Drew Barrymore in the professional debut of her own production company, Flower Films. Although the film’s clumsy but loveable protagonist Josie Geller is fundamentally different from the battle cries of the unapologetically feminist and self-confident Kat Stratford, Never Been Kissed is revolutionary in many of the same ways. Josie, portrayed by Barrymore in one of the best roles of her career, is the youngest copyeditor at the Chicago Sun-Times and dreams of being a reporter. One day that very dream comes true when she is selected by the loud head of the paper (Garry Marshall) to go undercover as a high school student to learn more about kids and teenagers today (well, in 1999). Although she jumps at the chance to finally be a reporter, Josie’s brother Rob (David Arquette) quickly reminds her that she didn’t exactly have the easiest of times in high school—cruelly nicknamed “Josie Grossie” by her peers, she was the epitome of the class nerd and it becomes evident that Josie, like most people, has not fully healed from the scars left by the relentless bullying. Nevertheless, she accepts the challenge and returns to high school, where she is very quickly befriended by nerdy mathlete Aldys (Leelee Sobieski) and begins to assume the same role she held in high school the first time. But soon, her boss Gus (John C. Reilly) insists that she must befriend the popular kids (Jessica Alba and James Franco are among them, in their film debuts) since that’s where the stories are, and not only does Rob return to high school as well to lead the charge but Josie is subconsciously falling for her English teacher Sam Coulson (Michael Vartan), who also has feelings for her. In the midst of showcasing Barrymore’s hidden talent and strength for physical comedy, Never Been Kissed emerged as a happy ending for all misfits—female or otherwise—who were bullied, ignored, and tossed aside. Kids who are bullied are taught that there will be a silver lining, but rarely was there a film or a character that accurately portrayed what it’s like to be that person in high school and carry those scars into adulthood. Never Been Kissed is Josie’s redemption narrative, and can serve as the same for anyone who sees themselves in her shoes. Like Kat Stratford, Josie Geller is strong and resilient—just in different ways. She may have not fully recovered from the torture experienced at the hand of the popular kids in school the first time around, but like most who are marginalized, she did emerge stronger from the experience. How else would she have conjured the strength to accept her first, triggering challenge as a reporter? Josie also reminds us that there is value in being bullied or misunderstood—that sometimes our greatest weakest is also our greatest strength—and opened the doors for other female narratives of the same nature: would we have gotten to experience the stories told by Bianca (Mae Whitman) in The DUFF, Nadine (Hailee Steinfeld) in The Edge of Seventeen, or even Kayla (Elsie Fisher) in Eighth Grade if it weren’t for Josie Geller? I’m doubtful. Never Been Kissed helped to forge the idea that geeks, nerds, and misfits are just as interesting if not more interesting than the popular kids.

Drew Barrymore on the set of Never Been Kissed with director Raja Gosnell (Source: Zimbio)

The main difference between 10 Things I Hate About You and Never Been Kissed, which both changed the game for teen comedy films in their own way, is the contemporary discourse that has followed them. The universal consensus is that, two decades later, 10 Things I Hate About You is a classic while Never Been Kissed has somehow not aged as well and is seen as mildly problematic. Since both films celebrated their twentieth anniversaries in the last two months, various publications have felt the need to assume a position on how the films have aged. Regardless of any indiscretions brought about by 10 Things I Hate About You, much of the literature surrounding its anniversary has been positive and celebrates how very few other teen comedy flicks—if any—have managed to replicate such a unique and empowering narrative. Never Been Kissed, however, has not been re-embraced as lovingly, since most publications have chosen to focus on the fact that Josie’s teacher Mr. Coulson actively develops feelings for her, someone he believed to be a student, and was angry at the discovery of her ruse. Anne Cohen from Refinery29 believes that what is more shocking and perhaps dated is that Josie’s boss insists that Coulson is “the story,” a.k.a. the man falling for the supposed student. She also writes that the film frames “inappropriate and predatory relationships either in the rosy glow of fantasy romance, or playing them for laughs.” In the same vein, Zoe Beaty from Grazia magazine claims that Never Been Kissed has distinctly misogynistic undertones from the very beginning since men at a newspaper are “obsessed with what schoolgirls are up to” (which isn’t the story at all; I have to wonder if some writers actually watch or rewatch the films they’re assigned to write about for a given anniversary). She also writes that the film “isn’t exactly… woke. Not at all, actually. Even at its most basic it’s about a successful reporter who won’t ever be happy with herself until the cool kids say she’s ‘sexy.’ But it did allow us to spend upwards of two months telling our friends that guys were ‘crunching’ on them (‘do I want to be crunched?’) and there are at least four dance routines to feast on.” I think they may be confusing Never Been Kissed with She’s All That, but what these and other publications fail to take into account is that Josie’s relationship with her teacher was a) not the point of the story and b) cannot be considered overtly inappropriate considering the newspaper, let alone the audience, knows that Josie is actually a consenting adult. In fact, Coulson’s first encounter with Josie in class is to ask if she’s really 17—implying that even he had his doubts. Still, the consensus surrounding Never Been Kissed is that it’s problematic because a teacher falls for someone he believes to be a student, and that the film harbors misogynistic undertones.

Look, misogyny is literally everywhere if you look hard enough. But what I think is misogynistic is the fact that, twenty years later, we’ve chosen to discuss how Never Been Kissed is somehow problematic for a plot point involving a man that is in no way the main focus of the story. Even Michael Vartan chimed in on the supposedly “creepy” nature of his character’s motives, saying he believed it’s completely inappropriate but did come to Mr. Coulson’s defense by stating, “I don’t think he lusted for her. It certainly wasn’t a physical thing. I mean, obviously she’s beautiful, but I think … he just sort of fell for her as a human being. He’s just really taken by her spirit and her soul and, you know, maybe deep down inside he felt like there’s no way this girl is 17, but on the surface, a teacher hitting on a student of any gender for that matter who is underage is completely inappropriate.” The film is Josie’s journey to healing past wounds and finding her professional calling, all while providing new representation for female nerds and misfits. Maybe we should focus more on that than the male supporting character who is now supposedly a predator when that’s not the deal. We shouldn’t force meaning where it doesn’t belong just for the sake of appearing current and relevant. 1999 was twenty years ago, and times change. Trends change, and people change, too. Things that cross a line or are considered risqué today might not have been seen that way twenty years ago for various reasons, and it gets even stickier if you go further back in time. It’s impossible for a single cultural text to hold up in every context for the remainder of time, but that doesn’t mean they always become invalid or necessarily “problematic.” Songs performed by Letters to Cleo probably wouldn’t fly in teen rom-coms today like it did in 10 Things I Hate About You. But whatever the interpretation, these two films were among many that set the tone for romantic comedies in the 21st century and new millennium, and without them we might never have met some of our favorite rom-com characters of the present day.