Two Cents Goes Back to School: 10 THINGS I HATE ABOUT YOU

Two Cents is a Cinapse original column akin to a book club for films. The Cinapse team curates the series and contribute their “two cents” using a maximum of 200-400 words. Guest contributors and comments are encouraged, as are suggestions for future picks. Join us as we share our two cents on films we love, films we are curious about, and films we believe merit some discussion. Would you like to be a guest contributor or programmer for an upcoming Two Cents entry? Simply watch along with us and/or send your pitches or 200-400 word reviews to cinapse.twocents@gmail.com.

The Pick: 10 Things I Hate About You (1999)

As we enter a new school year, we at Cinapse Headquarters decided to look at some of our favorite “school movies.” School makes for an amazing entry point for many filmmakers, as it serves as one of the few universal experiences. It also makes for a very rich setting for comedy, also a focus for us this month. Because we could all use a bit of frothy, school-based escapism.

Our original plans to post 3 “back to school” films this month was thwarted by film festivals, COVID, and other life stuff, but we couldn’t skip this 1999 high school gem that stars the late great Heath Ledger, alongside a who’s who of late 90s teen stars including Julia Styles, Joseph Gordon Levitt, Larissa Oleynik, Andrew Keegan, Gabrielle Union, and more.

For some of us it was the first watch, others a revisit after years apart, and for me… it was just my annual rewatch. If you grew up in this era, there’s a lot of nostalgic goodies in the one. We all seemed to enjoy ourselves this go around, so without having to get jiggy with it any more than we already have, enjoy our thoughts on this 90s teen comedy based on a Shakespearean classic. And be sure to share your thoughts in the comments, whether you were underwhelmed, overwhelmed, or just whelmed (onkly an option if you live in Europe).

The Team

Austin Vashaw

I never watched 10 Things even though I was in the target age during its release, completely disinterested in the twin fads of teen movies and formulaic romcoms that were blowing up at that time. Funnily enough, now that I’m an old man I kind of enjoy catching up on these movies out of nostalgia for that age and time – and in this case even more so, in appreciation for Ledger who was taken from us too early.

I do recall hearing that it was rooted in The Bard, which picked up my interest a bit (though not enough to ever watch it), and that’s one of its coolest traits. I dig all the Shakespearean references and Heath Ledger’s scene-stealing rogue – and appreciate that they just let him be Australian instead of trying to hide him behind an American accent.

Unlike Ed I’ve never been a fan of Julia Stiles but when she delivers her pivotal recitation  – a poem she wrote, which bares her soul and informs the movie’s title – wow. It’s a powerful moment and a stunning performance that hits hard.

By pure coincidence I also recently watched She’s All That for the first time – both films are really similar in their plots and cast of characters. I enjoyed that one more on a personal level – Rachael Leigh Cook being my Hollywood crush – but if I’m being honest, 10 Things feels a little more genuine in its telling.

(VforVashaw on Bluesky)

Frank Calvillo

Among the wave of teen movies in the late 90s/early 00s that presented audiences with modernized versions of Shakespeare, 10 Things I Hate About You remains this mini-genre’s crowning achievement. A surprisingly faithful adaptation of The Taming of the Shrew, the movie features a pitch perfect cast, all of whom are given standout moments and fully realized character arcs in genuinely funny movie that never once feels out of step with the times.

Thanks to director Gil Junger, the comedy in 10 Things I Hate About You is just superb. This fact shouldn’t come as a surprise given his resume, which includes writing/producing/directing duties for the likes of Empty Nest, Blossom, and Ellen. Junger is a filmmaker who knows when a laugh is needed for a scene and, specifically, what kind of laugh. From subtle ones, like David Krumholtz casually lifting a billiard ball off a pool table just as someone is aiming for it to Julia Stiles’ endless amounts of one-liners, Heath Ledger’s musical number, and basically any scene featuring Larry Miller (“those damned Dawson river kids”), the movie’s laughs are always plentiful and potent.

In the midst of the laughter are some genuine teen issues that are explored in a manner more thoughtful  when compared to other teen entries during this time. Topics such as teen sex and the trauma of divorce prove key plot points here. What makes this side work so well is that the movie never once talks down to the audience it was made for. Instead, it lets them know that they’re seen and understood.  It’s this kind of truthfulness one that makes 10 Things I Hate About You feel so totally in tune with the late 20th century teen landscape even if the text itself has been around for ages. At the same time, many of the movie’s 1999 aspects feel just as relevant today, a fact that helps earn its rightful classic status. I’d like to think even Billy would’ve been pleased. 

(@frank.calvillo.3 on Instagram)

Ed Travis

It’s quite rare that I’m at a loss for words in discussing a movie.

But in some ways, 10 Things I Hate About You represents a movie I’m almost comically unqualified to speak about. I’m conversant at best in the works of William Shakespeare, I’d consider romantic comedies to be among my least watched genres, and I am dangerously close to being categorized as a full on old person. So a teenaged romantic comedy Shakespeare adaptation isn’t something I’m going to be able to speak on with any kind of authority, expertise, or even point of entry. 

It’s a really damn charming film, though. And Cinapse programming some back to school films gave me a reason to sit down with my wife and daughter and enjoy this one together. It’s a little more sexually frank than I had remembered and might have been a little much for my daughter, but I think we had a great time. And if there IS any point of entry for me at all, it’s that the film harkens back to an era JUST immediately after my own high school experience. So I was kind of able to do the Leo DiCaprio point at the screen and say things like “hey, that’s a ska band”.

It’s a trope-filled tale dating all the way back to the Bard, but tropes never die for a reason, and 10 Things I Hate About You is incredibly satisfying. You also get a sort of etched in stone breakout performance from Heath Ledger who is so effortlessly charming, attention-grabbing, and iconic that you understand how he became such a legend in his tragically brief time on this earth. Growing up, I was more of a Save The Last Dance kind of guy, but Julia Stiles was a genuine Hollywood crush of mine and even all these years later, her presence is compelling. Only now I relate more to her Dad than any other character in the film.

I’m curious what my Cinapse teammates will have to say about this one that is perhaps more insightful than, “Hey, that’s Seattle”!

(Ed Travis on Bluesky)

Elizabeth Stoddard

Gil Junger was primarily known for his TV work (Nurses, Ellen, The John Larroquette Show, etc.) before directing 1999’s teen romantic comedy 10 Things I Hate About You. Loosely based on Shakespeare’s Taming of the Shrew, the story (adapted by co-writers Karen McCullah and Kirsten Smith) is packed with biting wit. Like their later project Legally Blonde, this screenplay contains a number of quotable lines (Gabrielle Union’s supporting character Chastity gets to deliver, “I know you can be overwhelmed and you can be underwhelmed, but can you ever just be whelmed?”). Besides the hilarious script, the film contains an impressive cast, from the teen characters to the adult authority figures.

Julia Stiles and Heath Ledger spar as a perfect grumpy match, supported by Larisa Oleynik (The Secret World of Alex Mack), Joseph Gordon Leavitt (Third Rock from the Sun), David Krumholtz (The Santa Clause), Susan May Pratt (Center Stage) and the aforementioned Gabrielle Union. Larry Miller, a Christopher Guest movie regular, plays the overprotective father of Kat (Stiles) and younger sister Bianca (Oleynik). Add in Darryl “Chill” Mitchell as a disgruntled English teacher and Allison Janney as a terrible guidance counselor who pens romance novels on the side, and you have a powerhouse cast.

On my most recent viewing (of the BluRay my sister gifted me on a past Galentines Day), I noted how perfectly the songs in the soundtrack are placed. The women-fronted music behind Kat’s scenes give us further insight into her feminist character. My brain automatically associates Semisonic’s “F.N.T.” with the film because of the colorful paintball kiss scene. Not to mention Ledger’s take on “Can’t Take My Eyes Off of You” while dancing in the bleachers. 

10 Things I Hate About You may not have aged perfectly (it’s old enough to rent a car at this point), but there aren’t many cringeworthy moments; it’s still a joy to watch every time.

(elizs on BlueSky)

Justin Harlan

Is this a perfect film? Probably not. But it’s nearly perfect to me. After seeing it in the theater and completely falling for it during my senior year in high school, I watched a few times throughout college then kinda drifted away until a few years ago. Since that time, I’ve rewatched at least yearly and it’s become a real comfort classic for me.

I’m not sure if everyone is like me, but I rewatch certain films often because they feel like a warm, snug blanket wrapped around me. This is definitely one of those. It harkens back to a time where the biggest problems I faced were teenage worries about the girl I liked or what I’d be doing Friday night with my friends. I miss that, especially in the world we currently live in.

On each rewatch, I seem to key in on a different person, a different story arc, a different unique flourish. In this case, I was fixated on Larry Miller’s Walter Stratford. I’ve always appreciated his witty dialogue, but on this occasion I genuinely found so many of the little comments he says as throwaways, even the little stuff he mutters under his breath, to be drop dead hilarious. Maybe it’s because I’m a dad of teenagers or maybe I just really needed the laugh and was keyed in on him more than before, but he was my highlight on this rewatch.

(@thepaintedman on Bluesky)


Next Month: Revenge of the Remakes

Next month, we celebrate spooky season with something a little different. Our staff chose some remakes that we enjoy as much or more than the originals. Each week, one of us will plead our case and we’d love to have you chime in to tell us if you think we’re crazy or we have a point. Or just chime in to share your thoughts on the film! See you in October!

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