10 Things I Hate About You: 10th Anniversary Edition courtesy Touchstone Home Entertainment

DESPITE JOHN HUGHES’ considerable output 10 years before, the 1990s were the real heyday of the teen comedy. Starting with the snappily hilarious “Clueless” in 1995, the genre came into its own during latter half of the decade and reached a peak in 1999, when “She’s All That,” “American Pie” and “10 Things I Hate About You” brought adolescents to the cineplex in droves. Working in a subject often written off as frivolous or pandering, these were smart, sophisticated films with a lively tone and a steadfast refusal (in most cases, at least) to condescend to their audience or characters.

As if to show high school students how a boring English class applied to their everyday lives, many ’90s teen movies found inspiration in literary sources, with which they engaged with playful knowingness. “Clueless” stands as arguably the best adaptation of Jane Austen‘s “Emma” and “She’s All That” recast George Bernard Shaw‘s “Pygmalion” among the lockers and proms. “Cruel Intentions” rewrote “Les liaisons dangereuses” as the proto-“Gossip Girl,” and perhaps most hilariously, “10 Things” tackled William Shakespeare‘s “Taming of the Shrew” with a sly wink.

“10 Things” is set at Padua High in Seattle, and concerns the efforts of Patrick Verona (Heath Ledger) to court the rebellious “heinous bitch” Katarina “Kat” Stratford (Julia Stiles, then just 17) — Verona and Stratford being the birthplaces of Petrucchio and Shakespeare, respectively. The students study the bard’s sonnets in their lit class, and one character (played by David Krumholtz of “Numb3rs“) attends prom as Shakespeare himself. The characters toggle between ’90s slang (“she’s without” being some sort of major compliment that’s forever locked in history) and Shakespearean dialogue (“I burn, I pine, I perish”). It’s a clever trick that suggests adolescents aren’t dumb or disengaged, but have developed a very complex view of the world and their lessons.

“10 Things,” which is getting a 10th anniversary edition less than a week into 2010, is the directorial debut of Gil Junger, who previously and subsequently worked on TV shows like “Blossom” and “8 Simple Rules … for Dating My Teenage Daughter.” He sets and sustains a wry tone that enhances rather than detracts from characters’ emotional conflicts. This new edition has only a few paltry features, but the new making-of reveals how much comic relief he added to the script, including Krumholtz’s disastrous motorcycle ride and an unfortunate arrow incident. The deleted scenes include a judiciously omitted bit with Junger himself playing a teacher who cracks painfully bad jokes.

The real reason “10 Things” is remembered a decade after its release — the reason it has become a cult movie on par with any of the ’90s teen movies — is the cast. Stiles gives her character’s anger some much-needed specificity; what could have been a vague bitchiness instead becomes witty, driven and even sympathetic. And no movie has used Ledger’s innate charms — those lively eyes and that easy smile — more effectively. Likewise, Joseph Gordon-Levitt exudes the same thoughtfulness that served him well in the brooding “Brick” and the bafflingly popular “(500) Days of Summer.” And in just a few scenes Alison Janney nearly steals the movie as a guidance counselor more interested in writing trashy romance novels than in giving helpful advice to her charges.

Of course, aspects of the movie haven’t aged particularly well. Some of the fashions will strike new viewers as dated, especially a particularly hideous pink prom dress, and the soundtrack wasn’t edgy even in ’99, so it’s especially lame in ’10. The movie begins with Barenaked Ladies‘ “One Week” and inhabits a world where second-rate No Doubts like Letters to Cleo and Save Ferris are considered “angry woman” music.

By far the best musical moment — and perhaps the film’s best scene — is Ledger’s infamous stadium serenade, when he sings “Can’t Take My Eyes Off of You” and runs from a pair of hapless security guards. It may not be Shakespeare, but such effortless charisma never gets old.

Written by Express contributor Stephen M. Deusner
Image courtesy Touchstone Home Entertainment