The Last Teen Movie
Why 10 Things I Hate About You is the defining film for a (micro)generation
We don’t talk nearly enough about 1999.
The last year of the twentieth century is now twenty years ago. Kids today must think of the nineties the way I thought about the seventies when I was a kid — as a mystical time and place, ancient.
I might be inclined to ignore the darker aspects of what all this means for me if I could actually avoid learning things like the fact that 10 Things I Hate About You came out twenty years ago last month. Teen movies from my formative years are twenty years old now. If the random body aches weren’t screaming it loud enough, this gets the message across: I am definitely, officially old.
My name is Chris and I am a Millennial. A lot of people my age want to resist this. We are, after all, on the cusp, with various authorities pegging the generation’s genesis anywhere between 1980 and 1984. More significantly, as the Millennially-averse always point out, there’s a massive difference in both the collective experience and collective character between people “like us” and “today’s Millennials.”
Fair points. But if we, especially having grown up in part without ubiquitous internet and entirely without smartphones, are different from our bizarre and oft-derided younger societal siblings, we are even more divorced from the character and experience of the Xers. (Come on, guys, you’d rather be associated with THEM?) We can quibble about labels all night if we want to — they are ultimately arbitrary anyway — but let me instead put it in terms we can agree on: this is a film that is unlikely to have much, if any, resonance with either our Gen X elders or the younger Millennial cohort. The film belongs only to us — to We’re talking about perhaps THE defining film of our micro-generation.
It was the 90s and the world itself was a paean to progress and peace. That’s really what we all thought. We hadn’t started the whole perpetual war thing, although we were about to. The world wasn’t going to end due to climate change, either; we had concerns like acid rain and the ozone hole and sometimes a little hand-wringing about landfills, but nobody said anything about the world ending, ever. They were still sending up space shuttles; Columbia hadn’t blown up yet and the Twin Towers were still standing.
I turned 15 in 1999 just days before 10 Things I Hate About You was released (opening second only to none other than The Matrix), and 15 is a big year for most people. It certainly was for me. It was here that I really began coming to terms with who I am and what I desire — the first real time I could experience and articulate the will of a (nearly) full adult. The summer found me deep over my head in a church camp pond in Hillsborough, not from the water but from the delusions and errors of First Love. There never was much to that story. I tell a lot of stories but never that one because it’s boring and I like to entertain people. But I remember what it was to me in that time and place and it was not boring, it was everything, and I don’t want to admit it but it deeply affected my life. In its aftermath, I was free for the first time to question and develop my own worldview and philosophy. I hadn’t yet tried any mind-altering substances (just you wait, 1999 Chris, just you wait), but it was also late in this year that I began occasionally and furtively smoking cigars, my first tobacco product.
It was the 90s and the world itself was a paean to progress and peace. That’s really what we all thought. We hadn’t started the whole perpetual war thing, although we were about to. The world wasn’t going to end due to climate change, either; we had concerns like acid rain and the ozone hole and sometimes a little hand-wringing about landfills, but nobody said anything about the world ending, ever. They were still sending up space shuttles; Columbia hadn’t blown up yet and the Twin Towers were still standing.
Do they still even make teen movies anymore? I shudder to think about what a teen movie would even be like in these dark times. I don’t envy these kids today; we at least got the first twenty-or-so years of our lives to believe that things were mostly fine and going to be all right. Granted, the prolonged shock we’ve all lived through as that rug was unceremoniously pulled out from under us has left us all deeply disoriented and a bit handicapped, but these kids never even got to have that. Ever since they first opened their eyes they’ve only ever seen a bleak future. How do you make a teen movie for that jaded crowd?
If you asked me back when I was fifteen, I definitely would have denied that I liked teen movies, but the fact was that I saw them all, mostly in the theater, and I liked a good number of them. We saw everything in the theater back then. There wasn’t anything much else to do as a fifteen-year-old beyond having someone’s mom drop us off at the movies, bowling, or maybe the mall (which was never fun because we didn’t have any money to buy anything). So we hit the movies a couple times a month, which means we’d end up seeing a diverse array, sometimes some weird shit, and pretty much every teen movie.
Sometimes at my parents’ house around the holidays, especially when my sister is around, I agree to watch things I normally wouldn’t go near. That’s how I once consented to watching Gilmore Girls(it’s actually halfway decent and I will still tolerate it being on). Two or three Thanksgivings ago, someone — probably my sister — decided to put on 10 Things I Hate About You. I found this idea interesting because it was high on the list of movies that were significant when I was in high school that I hadn’t revisited in almost two decades.
I braced myself for the cringing.
Except…there really wasn’t any. I was pleased to find that not only is it passable, but it’s respectably odd and legitimately quite funny. I’m notoriously fussy and negative when it comes to comedies, so I definitely did not expect to laugh at this teen movie in my 30s. It’s not even like this was Superbad or something; as far as 10 Things is a comedy, it’s solidly a romantic comedy. And at the risk of revealing myself a babbling fool, I’ll say the sentimentality actually still catches me pretty good. That’s not to disparage sentiment and romance in film, but I keep that bar really high, and somehow this weird little movie clears it.
The thing holds up. It’s a legitimately good film.
(A couple weeks later, enthused by this experience, I decided to revisit She’s All That, a contemporaneous teen movie that held a similar standing in my high school year, has a similar theme, and also features a famous dead actor. It does not hold up. It is not a good film.)
I would call out a few key factors as critical to its success: the cast, the purity of its late-90s character, the way it’s somehow smart and aware while handling ultimately standard teen movie fare — avoiding cliches and simplistic social roles in the process — and the way it’s not afraid to be weird without explanation or apology.
Given that it effectively launched the careers of Julia Stiles, Heath Ledger (RIP), and Joseph Gordon-Levitt, it’s no surprise that the cast gets a lot of the retrospective attention. Beyond the obvious, I’ve got my own personal reasons. Larisa Oleynik, if anyone remembers, was Alex Mack, indisputably my biggest middle school movie/television crush. And who ended up being my biggest high school movie/television crush? Julia Stiles. Looking back, that had to have started with 10 Things I Hate About You. I still have a soft spot — I was tickled to catch a glimpse of her in The Silver Linings Playbook as Bradley Cooper’s buddy’s uptight wife. I feel like we don’t see enough of Julia Stiles these days.
Six years after 10 Things (and before he transformed into Edward Snowden more thoroughly than even Johnny Depp inhabited Hunter Thompson) Joseph Gordon-Levitt won my heart for life starring in a (very) different high school movie; Brick is unquestionably one of my favorite films of all time. Heath Ledger seems to have been a good fellow, however hard it may have been to predict that he would go on to have a baby with Dawson’s Creek and die from playing the Joker, and then there’s also the hilarious Santa Clause elf guy.
Not nearly enough gets said about Andrew Keegan, who plays the film’s delightful villain, a chisel-faced, musclebound, dumb-as-a-rock teen model. His filmography may be the most modest of the film’s stars (perhaps more so even than Krumholtz), but a second look shows just how deeply interwoven he was in the critical culture of my microgeneration. He appeared in Full House, Step by Step, Moesha, Boy Meets World, Sabrina the Teenage Witch, Independence Day, and Party of Five — not to mention his most prominent role outside 10 Things, playing Jessica Biel’s nice on-and-off single dad boyfriend on 7th Heaven. He even returned to both Julia Stiles and weird Shakespeare adaptations a couple years later with 2001’s O.
What’s even more significant to me is his personal life; in some ways, he’s a bit of a role model. After semi-retiring from his status as an lower-high-tier (or maybe upper-middle-tier?) teen idol, he started his own cult in 2014! It was called Full Circle and lasted for three years. It seems to have been loving and delightfully off-beat, while apparently avoiding extreme or problematic beliefs. Keegan never declared himself a prophet or a saint or a son of any holy being. No accusations of sexual impropriety (never mind sexual slavery — AHEM, NXIVM) have been made, nor did anyone embezzle any money. They DID once get raided by the state of California — for the controversial practice of selling kombucha without a license. I’m not making any of this up, and there’s definitely lessons to be learned here, maybe even examples to be followed.
(I can’t seem to find out why Full Circle dissolved — I think maybe they just ran out of cash — but Keegan also has a great Instagram, where you can find him becoming a father for the first time and surfing, and until I hear stories to the contrary, I think we can assume he’s actually a legit good guy. Good enough that we might overlook his lack of follow-through as cult leader.)
I’m not sure of a better song to start off an iconic micro-generation-defining 1999 teen movie than Barenaked Ladies’ “One Week”, which is quickly subverted as the camera lands on Julia Stiles’ Kat driving some kind of 70s car blasting Joan Jett’s “Bad Reputation”.
It becomes clear pretty quickly that this is a little different from a half-assed teen flick when we are soon introduced to Allison Janney’s weird guidance counselor, who cheerfully swears at and dresses down the students as she works on an erotica novel on her laptop.
She’s far from the only strange minor character. Chief among them is almost certainly Bianca (Oleynik) and Kat’s neurotic (and single) OB/gyn father, who obviously loves his daughters but is so obsessed with their sexual purity that it would put Old Testament patriarchs to shame. He delivers some pretty fun lines, greeting Kat after school with, “Make anybody cry today?” After Kat intentionally drives into villain model Joey’s (Keegan) convertible, an act that seems to have minimal consequences in the universe of this movie, he shouts, “My insurance doesn’t cover PMS!” It’s a line much less likely to appear in movies twenty years later, obviously because it’s a crude way of reducing the emotions and interests of women to sex-driven biological insanity, but even as we laugh, he’s not getting away with any of it. When he forces Bianca to wear a ridiculous pregnancy suit around the house as a sexual deterrent prior to a party, we in the audience know not just that he’s being inexcusably patriarchal but that he is patently absurd — and we see this in a subtler, more nuanced way than I would expect today. In 1999, believe it or not, we were trusted enough to understand that he could be a well-intentioned and loving single father and hold deeply neurotic and misogynistic views on women and sex. (As in the source material, Shakespeare’s The Taming of the Shrew , both daughters spend much of the film rebelling against this quality of their father).
It sounds like a teen movie trope, but 10 Things isn’t content with that and the “standard prom scene” is anything but. Joey the villain, three times the size of Cameron, calls Bianca a bitch and Cameron angrily tells him he’s crossed a line. Joey punches him once and he drops to the floor. A lesser movie might have the scrappy, skinny, slightly-nerdy protagonist come into his own by fighting back and defeating the bully, but instead, here, it’s Bianca — who isn’t even the shrew — who flies into a cool rage and punches Joey three or four times while telling him off. She then reaches down to help Cameron up and ask if he’s all right, which he is — without any trace of wounded masculine pride.
In the world of 10 Things I Hate About You, solid and confident guys can be physically defended by their would-be girlfriends with no shame, and sweet, pink-attired girls can punch bullies on behalf of would-be boyfriends without any respect being lost. Through Ledger we see that hard-edged loners can be moved, under the right circumstances, to hijack a stadium loudspeaker and declare love by singing Frankie Valli and dancing away from hapless security guards.
In Kat — our “shrew” — we see that even cold and severe people are not just capable of love but need it and fall victim to it, and in the best of times they can give themselves over to it sincerely, without hedging or even masking it in sorrow.
It’s worth noting that when Stiles, at the end, reads the poem from which the film takes its title, her tears are real and unscripted and what we see in the film was actually the first and only take of that scene. And yes, I tear up watching it, too, because this is such a good teen movie that I still feel it at 35, all these years and miles away from being an actual teen. Maybe that’s because it’s good at conveying these universal human emotions, or at getting us to remember what it was like back then, or maybe that’s only the case because I recognize the 1999 of the movie as being the real 1999, a place in which I once walked and lived, a place that’s still with me even though I don’t usually know it.
The most obvious thing that stands out about the 90s in comparison with today was its sincerity. In 2019, we’ve reached a point at which things are occasionally referred to as post-ironic. For example, starting in a couple of weeks and lasting until September, I will wear a post-ironic summer mustache. It’s post-ironic because through the emergence around ten years ago of the ironic mustache, I dared to wear one a couple of times “as a joke,” which led me to the realization that I actually just like mustaches and wearing a mustache, in all seriousness and without any of the irony.
Could Sister Hazel’s “Your Winter” have been written today? Or any of the Letters to Cleo songs? Listen to damn near anything from in or around 1999 and (especially now that you’re looking for it) it’ll hit you in the face. All of these people singing are serious, they mean it, and they aren’t ashamed of it. They don’t seem aware of any reason to be ashamed.
The 90s (especially the early-to-mid-90s, still in the throes of Generation X’s fleeting reign) believed itself to be very jaded and cynical, but they couldn’t have known what they didn’t know, and the second half of that decade, approaching the millennium, was a lot different from the first. We may be sitting here in post-ironic 2019, but 1999 was positively pre-ironic. You can tell, looking back — even some of that cynical veneer applied in the first half of that decade had washed out and faded. There’s a certain earnestness, a shocking lack of fear when it comes to openly caring about something or someone, especially as pertains to falling in love and pursuing it. This marks a very distinct point in time; I would argue that the early 90s was too cool to cop to falling in love, while our modern day is too dull and sterile to tolerate romantic pursuit.
Setting aside musical quality and talking only about that sincerity, could Sister Hazel’s “Your Winter” have been written today? Or any of the Letters to Cleo songs? Listen to damn near anything from in or around 1999 and (especially now that you’re looking for it) it’ll hit you in the face. All of these people singing are serious, they mean it, and they aren’t ashamed of it. They don’t seem aware of any reason to be ashamed.
In fact, as I was writing this piece, a fellow Millennial writer actually commented that Cameron (Gordon-Levitt) could never have ended up with Bianca because nobody who actually wants something that bad should or does ever get it. Well I’ve got news for you (JOHN) — another reason I connect with this film is that back in 1999 (and for a few years after) I actually was like Cameron. Sweet and innocent, prone to fall in love for sometimes-thin reasons, but determined and unwavering about it, over-the-top sweet, all of that. And let me tell ya —plenty of times does someone so into someone else actually win the heart of the pursued. At least, that’s really how it was in 1999, when we could be earnest and sincere and actually want people and things without shame or self-censorship. (It’s possible it was never like that in New Jersey, I don’t know.)
I may have just published a piece in which I renounce and deny nostalgia — and I stand by it — but 10 Things I Hate About You does evoke a lot of fondness I have for 1999, for the time in which my microgeneration, “the older Millennials”, came of age. It’s a reminder that for a moment we were a little bit earnest and sincere, that we had yet to know of the disaster and decline and catastrophic unease that would befall us in the decades to come. In 1999, you could still fall in love and chase it, sing about it, fight for it, and mean it — and you could make a movie like this one.
Some things, perhaps, are worth hearkening back to.