Cameron James (Joseph Gordon-Levitt of 3rd Rock from the Sun, The Lookout and most recently (500) Days of Summer) has just started attending Padua High (named after the city from the classic play) and is immediately dumbstruck by the beautiful and popular Bianca Stratford (Larisa Oleynik, who also had a brief run in 3rd Rock). Much to Cameron's despair, his new friend, Michael (David Krumholtz, now known for his role in TV's Numb3rs), advises his that she is forbidden to date by her father (Larry Miller). This fact about Bianca's chastity also makes her the focus of many boys at school, including rich male-model Joey Donner (Andrew Keegan, who later played in another Shakespeare adaptation with Stiles in O).
As both Cameron and Joey attempt to get close to Bianca, the Stratford girls' father decides to change the rules a little. Instead of simply forbidding her to date, he says that Bianca can date whenever her older sister, Kat (Stiles), goes out. Since Kat is rough around the edges (to say the least) and causes arguments and turmoil pretty much wherever she goes, he feels this is a safe bet, but what he doesn't realize is how determined the boys around Bianca can get.
Upon learning of this new change in the rules, Cameron and Michael start up a new plot. They need to find someone who has a rough enough hide to actually stand being near Kat. The problem is not only convincing someone that it is worth their while, but also getting Kat to like him. Enter Patrick Verona (Ledger). This Australian boy has a bad reputation. Rumors fly all over the school about where he was the last year (some think jail), people he might have killed and other nefarious things, but Patrick isn't just going to start dating the older Stratford girl for no reason. So with a bit of scheming, Cameron and Michael convince Joey that it is in his best interest to pay Patrick to date Kat, so that Bianca is available for dating. This starts a strange relationship between Kat and Patrick as the two start butting heads, but eventually start to fall for each other. Of course, even if you haven't seen the movie before or haven't read the play, you can probably guess what is going to happen when Kat finds out exactly why Patrick is suddenly interested in the leading lady. Meanwhile, Cameron's side of the story gets even more convoluted when he, Bianca and Joey end up in a love triangle and Bianca has to decide if she would prefer the popular pretty-boy or the kind, nice guy.
10 Things I Hate About You is not only a great romantic comedy (based on one of the first romantic comedies), but it's also a great look back at the early careers of so many young actors. While there is a bit of a sad note watching it knowing that Ledger won't be making any more movies (though his last production, The Imaginarium of Doctor Parnassus, is just hitting theaters), the retrospective featurette featuring current interviews with Director Gil Junger and Writers Karen McCullah Lutz and Kristen Smith, combined with interviews of the actors from the time, offers a good look back at the movie as it was and what its done, even if it doesn't focus on Ledger a whole lot.
10 Things I Hate About You is one of those movies I could watch over and over again. The characters don't feel like stupid teenagers, the writing is great (complete with the occasional injection of Shakespearian lines) and it's just a great story. If you don't already have the film, then definitely pick up the 10th Anniversary Edition; if you already have it, then there isn't really a need to repurchase the movie, but at least dust it off and give it another watching.