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.
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.
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