I know there are some classic teen movies from the 1980s (Fast Times at Ridgemont High, 1982) and certainly from the early 2000s (Mean Girls, 2004) but I still say the 1990s were the peak of the high school set subgenre, at least in terms of prevalence. My favorite of this decade, and possibly of the entire subgenre, was always 10 Things I Hate About You (1999). When “Is It Still…” became a feature here, I realized that it would be the perfect opportunity for me to step back and ask myself why I’d loved this movie so much— and whether it’s still worth loving now.

10 Things I hate About You is a loose adaptation of William Shakespeare’s The Taming of the Shrew. The plot works quite well as both teen comedy and Shakespearian comedy (with that modern, youthful twist, of course): Cameron (Joeseph Gordon-Levitt) falls for a beautiful, popular girl named Bianca (Larisa Oleynik), who can’t date until her older sister Katarina (Julia Stiles), a non-conformist, feminist “shrew,” does. Cameron recruits a rebellious bad boy (Patrick Verona, played by the late Heath Ledger) to woo Katarina (so that he may date Bianca), and they end up falling in love despite the usual miscommunications and predictable big reveals.

The script is, for the most part, surprisingly smart; the Shakespearian comedy of errors comes to life in a high school setting in a way that seems mostly natural, and yet, the film also insults our intelligence by making awkward and overt gestures toward the Bard himself, winking obnoxiously at us through the character of Mandella who is obsessed with Shakespeare. It’s a bit distracting. But, out of the entire film, nostalgia aside, this was only one of only two new, less than positive observations I had.

Almost everything else holds up: Heath Ledger and Julia Stiles as our leads have convincing chemistry as mutually outcast lovers, and they certainly share some iconic scenes together— who could not still love Ledger’s serenade in the bleachers? There are also hilarious minor characters who are absolute scene stealers: Allison Janney as Ms. Perky, the school’s guidance counselor who would love nothing more than to finish her erotic novel; Daryl Mitchell as the snarky, street smart English teacher, Mr. Morgan; Larry Miller as the overprotective, overbearing father to Bianca and Kat. And, though some of the jokes attempt a kind of mature crudeness but fall back on their juvenility, others land just fine, even now. The characters, main and supporting, are all mostly likable; however, they’re not wholly realistic.

Julia Stiles plays Katarina perfectly, with an intelligent angst. But the archetype she portrays is just riddled with issues—as a teenage feminist in the late 90s, she’s seen rocking out to girl bands and reading Sylvia Plath. She’s portrayed as being deeply unlikable in the eyes of her peers, not simply because she is belligerent but because she is embodies this man-hating form of feminism. The one-dimensional, stereotypical approach the film takes to its characters— but particularly to Kat— is as lazy as one could expect from such a movie. Yet, while man-hating isn’t the goal of feminism but rather a negative and inaccurate connotation of feminism, Kat was a character who didn’t feel like she needed a boyfriend, and she didn’t conform to the trends around her. As a female role model, she was awesome, and she didn’t need to be “tamed” all that much in order to get the guy either. Was she empowered by all this? To some degree, maybe. I simply wish her feminism wasn’t such a big factor in portraying her as the “shrew” that needed “taming. ” She was smart, savvy, and strong though, and for all the potential pitfalls of her characterization, I can’t help but think she was still pretty cool.

So, I’m conflicted about this film, having revisited it with a more discerning eye. I think as a teen comedy, it’s still pretty great, yes. It’s not as quotable as Clueless (1995), but it’s also not as rooted in its era. When I saw 10 Things I Hate About You more recently, I thought it seemed more or less fresh and not as tied down to its decade, and I think that’s definitely a good thing. I guess I’ll just say that, now that I’m older, these bigger questions— mainly those pesky misconceptions of feminism— definitely stuck out to me more. Do the presence of such questions make the film any less great? No, not necessarily.

Does it mean the film is and probably always was imperfect? Definitely. It’s a fun, fairly intelligent teen comedy, and I certainly couldn’t think of 10 things I hate about it! And I think for a sort of feminism to be featured in it at all was a step in the right direction at the time. I just wonder how far we can trace that trajectory—as well as the tradition of literary influences on these films, while we’re at it— to more recent examples like the Twelfth Night-inspired She’s The Man, or Easy A which endlessly references The Scarlet Letter. Maybe 10 Things I Hate About You and its female protagonist have had a more complicated and compelling impact than any of us could have realized. Or, maybe it’s just another teen movie after all. Personally, I’m actually okay with either interpretation.