How does one try to summarise 1999 with one review of one movie? It was arguably (by which I mean "almost certainly, but let's not be smug know-it-all dicks about it") the single most transformative year of American filmmaking after the collapse of the New Hollywood Cinema. A stunning number of major filmmakers made some of their most important films that year: Stanley Kubrick, Paul Thomas Anderson, Michael Mann, David Fincher leap to mind, while Spike Jonze, Sam Mendes, the Wachowskis, Kimberly Peirce, Alexander Payne and M. Night Shyamalan all made their debuts or had their big breakthrough. Technology advanced by leaps and bounds, starting with the Wachowskis' The Matrix and continuing through the year's highest-grossing film, Star Wars: Episode I - The Phantom Menace, with its groundbreaking use of all-CGI characters and CGI-augmented sets. Animation had a banner year, as did horror. American Pie brought back sex comedy in a big way, and we've had a golden age of raunchy humor ever since.

It's simply not possible to grab all of those threads and collect them in one essay, so I didn't bother trying. Instead, I elect to focus on just one of the many cinematic trends that passed through the bottleneck of 1999, the fad that dominated the second half of the decade of adapting classic works of literature into the high-stakes world of American high school. I confess that my choice was aided by the years and years I've been told that I absolutely needed, just needed right the fuck now, to finally see 10 Things I Hate About You. This was serendipitous: while I can't swear to its timeless important in the development of cinema the way the way I might about Fight Club or The Sixth Sense or even something totally disreputable like The Mummy, I don't think I could have consciously come up with anything that more perfectly captured what the late '90s felt like if that had been my sole intention. Also, everyone who told me was right: I did, in fact, needed to see it right the fuck now, because on top of everything else, it's one of the absolute best teen-driven romantic comedies that I have ever seen.

So, about that perfect embodiment of 1999: herewith, a motion picture that stars Julia Stiles, whose name is featured drawn in bold, sketchy style in magic marker colors during the opening credits, while the Barenaked Ladies' "One Week" bounces its way across the soundtrack. The film at least has the forward-thinking wisdom to make this last detail a joke: the undying Ladies dominate the soundtrack until until we see Stiles herself pull up to a red light next to a bunch of giddy, pop-loving girls, blasting Joan Jett's "Bad Reputation" loud enough to drown them out. I cannot say whether the filmmakers planned for this to be a sign that her character, Kat Stratford, is completely awesome or a bitch; but it made me like her a lot, anyway.

The awesome/bitch divide is, in many ways, the heart and soul of 10 Things I Hate About You. For the film is a dressed-up retelling of The Taming of the Shrew, a late entry in the great explosion of William Shakespeare adaptations that flourished in the 1990s, on top of the "put it in high school" trend that had been purring along steadily since Clueless in 1995 (the Venn diagram combining these two trends also contains William Shakespeare's Romeo + Juliet and O, and I believe nothing else; though it wouldn't do to not at least mention the modern dress Hamlet with Ethan Hawke). And The Taming of the Shrew brings with it an amount of baggage like no other Shakespeare play outside of The Merchant of Venice. To wit, the play's sexual politics, which may or may not be as straightforward as they seem (the amount of irony to be read into the last scene is not, that I am aware, a settled matter), but they seem pretty damn toxic. And this makes any modern treatment of the play a project that needs to be handled with delicacy, especially a modern treatment set among teenagers.

So while we are surely meant to recognise in Kat a certain stiffness and problematic standoffishness - there couldn't be a plot if she didn't have to be redeemed in some way - Karen McCullah & Kirsten Smith's screenplay also has to allow plenty of room for us to like her just the way she is, a blunt, tough-talking punk kid with an appealingly sharp tongue. To a certain degree, the writers game things by surrounding Kat with transparently unacceptable people: her sister, Bianca (Larisa Oleynik) is a shrill, bubble-headed twit (established early and firmly in a beautiful line of character-establishing dialogue: "I like my Skechers, but I love my Prada backpack"), and her father Walter (Larry Miller) is a deranged anti-sex lunatic, owing to his work with pregnant teens. It's impossible not to like the "bad girl" when the people she's being contrasted with are so immensely vacuous. And so we end up not with Kate the Shrew, but with something more complicated and ambivalent: Kat the Riot Grrrl but also Kat with the Self-Negating Priorities. The character is a bit artless, and Stiles's clipped performance in the film's early going doesn't do much to flesh out the humanity in a distinctly artificial part, but it's perhaps the best that could be done.

Anyway, the film mostly follows the story play quite closely, doing a decent job of finding analogues for things that need updating: the newcomer to Padua High is one Cameron James (Joseph Gordon-Levitt), who falls hard for Bianca on day 1, only to find that her father has forbidden both of his daughters to date before college. Except that he's just changed the rule a little bit, in a bit of nasty-minded sophistry worthy of Cinderella's stepmother: Bianca can date only when older sister Kat has a boyfriend. And since Kat has decided that she's better than every other person attending Padua and would rather die than touch any of them, this is as good as a chastity belt. Except, that Cameron and his friend/co-conspiracist Michael (David Krumholtz) come up with a plan: hint that his his rival for Bianca's hand, Joey (Andrew Keegan), should pay to hire somebody to ask Kat out. And the target is the sullen, alienated bad boy Patrick Verona (Heath Ledger), one of the only people at Padua who can go toe-to-toe with Kat on her snarling antisocial nastiness.

If 10 Things I Hate About You ends up falling into a lot of the narrative rhythms of any old romcom, this is at least partially because Shakespeare's plays did a lot to invent those rhythms: not the grimly de rigueur bit where the third act needs to be ushered in by the discovery of a terrible secret taken somewhat out of context, and the lovers have a fake fight (something that wasn't as ossified in 1999 as it is now; I think 2003's How to Lose a Guy in 10 Days is what carved it into stone). I expect that nobody could be genuinely surprised by the direction the plot headed, even if they hadn't read the play, but formulas do not need to aplogise for themselves when they're executed well; this is a lesson that the works of Shakespeare teach us if they can teach us anything (after all, all but three of his plays were remakes). And in 10 Things I Hate About You, the formulas work splendidly, thanks largely to the energy with which McCullah & Smith draw their characters, and the way Gil Junger directs his awfully solid cast into a breezy, bantery register of dancing at each other with salty quips. It proves once again something that should have been obvious since the 1930s, but never seems to stick for very long these days: romantic comedies are best when they play as a series of verbal battles of bright, staccato dialogue, and then that dialogue is as filthy as the circumstances will allow. In the screwball era, that meant high-concept innuendo. In the case of the PG-13 10 Things I Hate About You, that means a lot of surprisingly bold chatter about sex that avoids feeling raunchy solely because the actors always speak their lines like they're trying to score points against a debate opponent, rather than because they actually seem to be thinking much about sex. Which I mean as a compliment.

There's too much naturalism in the film, particularly in the form of Ledger's bracingly caustic performance (it was the film that put him on the map, and while it's not at all one of his best performances, it's obvious throughout that he's got some real acting chops, far beyond the usual teenybopper pretty guy), for it to feel like a long-lost '30s film made about '90s teens, though honestly, the pacing of it is much closer to that than to the logy romcoms of the modern era. For all that the hook and the soundtrack make it sound like a generic teen-audience cash-in, the film is shockingly committed to functioning as a character-driven comedy, and when Stiles starts to loosen up as her character gets more flexible, it turns out to be a pretty delightful one.

Genre will be what it will be, and there's nothing surprising in 10 Things I Hate About You at the level of writing, and nothing remotely inspired or memorable at the level of film craftsmanship: it has the stolidity of the modern romcom, cleanly lit and squarely focused. But it's got good bones: a sturdy structure on which well-built jokes are arrayed, delivered with in-character nuance by a relaxed, enjoyable cast (also appearing: a delightfully curt Allison Janney and a frightfully fresh-faced Gabrielle Union). Nothing world-changing, and in 1999, films that were content to be the best piece of finely-tuned entertainment they could be seemed about as unambitious as at any other time in history. But for all its period trappings in slang, in style, and in tone, the film has aged well: good meat-and-potatoes filmmaking is never easy, and it's certainly never disposable. 10 Things I Hate About You is low-key and has small goals, but the way in which it meets those goals is in line with the best tradition of audience-pleasing Hollywood craftsmanship all through the years.

Elsewhere in American cinema in 1999
-South Park: Bigger, Longer & Uncut becomes the highest-grossing adults-only animated film of all time
-Samuel L. Jackson makes a memorable exit from Deep Blue Sea
-Austin Powers: The Spy Who Shagged Me is one of the largest hits ever greenlit on the basis of its predecessor's cult success on home video

Elsewhere in world cinema in 1999
-Filthy-minded Spanish melodramatist Pedro AlmodΓ³var suddenly has an enormous critical smash with the sublime All About My Mother
-Kang Je-gyu's Shiri is the first homegrown megablockbuster made in the rejuvenating South Korean film industry
-French madman Leos Carax makes certainly his hardest, and maybe his best film, Pola X