Outstandingly, 10 Things I Hate About You is 25 years old. And despite the end-of-the-90s vibes, the film remains a staple in teen comedies.

The film is a modern adaption of William Shakespeare’s “The Taming of the Shrew.” Akin to the Shakespearean play, the film follows sisters Kat (Julia Stiles) and Bianca (Larisa Oleynik) who could not be any more different. Bianca, the younger of the two, is traditionally girlie and particularly boy crazy, setting her sights on popular blowhard Joey (Andrew Keegan). Meanwhile, Kat likes Thai food, feminist prose, and angry girl music of the indie-rock persuasion, and largely dislikes most of her peers. Where Bianca is cheery and affable, Kat is literally introduced by the Joan Jett song “Bad Reputation.” But the film takes a turn when Bianca and Kat’s overprotective father (Larry Miller) allows Bianca to date, once Kat does. It inspires new kid Cameron (Joseph Gordon-Levitt) to hatch a plan: convince Joey, who wants to date Bianca, to pay bad boy Patrick (Heath Ledger) to date Kat; meanwhile, Cameron will help Patrick woo Kat as Cameron himself tries to win Bianca over.

It takes the classic comedy of errors, but elevates its source material by being so tuned in with its characters. Most teen comedies, whether from the 90s or current-day, rely heavily on stereotypes. The jocks, the nerds, the pretty girls. But the secret weapon to 10 Things I Hate About You is the way in which it subverts character expectations. Bianca is pretty and sometimes self-centered, but she is also protective of her sister and wants to be seen by others. Kat is highly intelligent and wildly opinionated, but she also cares deeply for her sister and wants to be loved for who she is. Cameron may be come across as the nice guy, but he can also clueless and a touch pious. Patrick appears to be a dangerous bad kid, but deep down he’s caring and attentive. Everyone, albeit maybe not Joey, has layers and textures which help them shy away from caricatures of teenagers. 

This is also aided by the film’s impeccable cast. Stiles expertly navigates what could be considered a thorny character. She never belittles Kat’s passion or her personality. Women and girls have always been expected to be “likable” as a protagonist. Yet, Stiles as Kat is unapologetically herself. She is intelligent and opinionated and uninterested in the status quo. It’s certainly a representation of girlhood that made an imprint on many young girls who would grow up to be their own versions of Kat. Meanwhile, Oleynik as Bianca nails the comedy and sincerity of a seemingly dismissible teenage girl. In a less capable hands, Bianca would be reduced to her looks and her popularity. Oleynik always ensures that her earnestness and optimism shine through.  From Ledger to Gordon-Levitt, Gabrilelle Union to David Krumholtz to Allison Janney, everyone brought some depth to their character to provide complexity and layers to this world. 

Yet, none of these elements would be abl to soar without the screenplay written by Karen McCullah and Kirsten “Kiwi” Smith. McCullah and Smith were tapped into the pop culture of the time, giving this group of teenagers believability. They watch The Real World and listen to The Notorious B.I.G. And still, even with that late-90s specificity, they added a timeless quality to the script. High schoolers will go to parties and have the biggest feels and desperately want to be seen. They are complicated and messy and silly and trying to figure it out. Without this heart at the sent of the screenplay, the delicate balance between sincerity and the comedy would be off-kilter. The comedy of this film is truly iconic. There are lines that are so sharp and witty, they can still make you laugh 25 years later. (“Remove head from sphincter, then drive” is a classic). The comedy is quick and smart. But it is not merely the comedy that sticks out. McCullah and Smith crafted some influential scenes that have stood the test of time. The scene when Ledger sings “Can’t Take My Eyes Off You” on the bleachers became so ingrained in pop culture that it was parodied in “Not Another Teen Movie” (2001). And, most notably, the sonnet Kat Stratford writes and reads in class has become a scene which embodies the best of teen comedy films. 

On a personal note, 10 Things I Hate About You crafted my younger self’s sense of humor. To this day, I will make comments about being just whelmed, or jam to Letter’s to Cleo cover of “I Want You to Want Me.” Coming out just before the paradigm shift brought on by easier access to the internet and social media, the film gave me an example of girlhood that was outside of the expectations of the aughts. That existing as a teenage girl did not mean I had to make myself small for men.  It taught me that “likable” was a subjective word that was largely weaponized against women. It showed me that I could be smart and have strong opinions and be worthy of love.  And it gave me the tools to be able to spot a Joey Donner from a mile away.  

The reason that 10 Things I Hate About You has stood the test of time is not just the comedy which still makes me laugh to this day. (I know the jokes are coming too!) 10 Things I Hate About You empowered a generation of young women to just exist in our truths. I know for myself my self-assurance and high school obsession with Sylvia Plath are directly related to this film. A quarter of a century later, 10 Things I Hate About You continues to find new audiences. I just hope that the next generation of girls can find the same magic in this film that I did.