Movie Review – 10 Things I Hate About You (1999) *****

In this Y2K remake of Taming of the Shrew, an overprotective father prevents his teen daughters from dating unless both of them go out. The younger sister convinces guys to get her shrewish older sister hooked up. Enter Shakespearean shenanigans: One guy talks another guy into financing a third guy into dating the older sister, presumably so that the financier can date the younger sister, but *actually* so the first guy can date her. The younger sister does actually want to date the financier. But the ones who fall in love are the third guy and the oldest. Are you keeping up?

You can transpose Taming of the Shrew onto any generation, but this one effortlessly touches down on late-90s Hollywood High School. The daughters of a rich family have so many of the same concerns about finding appropriate matches — although here, the matches matter for school reputation and a father’s approval, not marriage.

Our hero-for-hire, Patrick, is played by handsome young Heath Ledger. He’s gorgeous in this movie. His curls! His bone structure! The intensity when he worries over Kat! He played a bad boy with arresting tenderness, and he remains a complete heart-breaker. I’m thirty-old now and I’m still like, damn, just as much as when I was a kiddo.

I always found Kat so relatable — played here by Julia Stiles, dancing slightly better than she does in Save the Last Dance. (Can we please note how she really got thee best romantic heroes in her early movies? Heath Ledger, Sean Patrick Thomas, Freddie Prinze Junior…) Her bad attitude has been my entire life goal.

It’s funny how Kat is built up like a stereotypical lesbian in many ways — her fashion sense, her music preferences, the books she reads, her school of feminism — and I feel like the sequel would have her character discovering lesbianism in college, yet I also totally believe her chemistry with Heath Ledger. I bet a lotta lesbians would have made him their exception.

How could you *not* fall for a boy so committed to keeping you awake after hitting your head drunkenly at a party? Or who tries to win you back by performing a huge song with the marching band, while also fleeing from cops? One who uses his illicit gains to buy you a friggin guitar? I can’t even.

Though the romance is what kept a lot of us coming back when we were young teens, I really think what makes this movie persist twenty-five years after its release is the goofy humor. 10 Things walked so that Bottoms could run. Which passing gag is the funniest: the cowboys using their lariats on trash cans, the PE teacher getting shot in the butt by an arrow, Joey Donner’s terrible modeling, the penis on Michael’s cheek, the kid weirdly interested in sheep…?

On a personal note, this is one of the few movies where I still haven’t mentally transitioned from relating to adult characters from the teen characters. When I watched Addam’s Family as a kid, I was Wednesday; I have been Morticia for over a decade. But something about 10 Things I Hate About You makes me regress completely to being in high school again. Falling in love with Heath Ledger again. Drawing boobs on cafeteria trays again.

(image credit: Buena Vista Pictures Distribution)