Everything I know about life, I learned from the teen romantic comedy boom of the late 1990s.
This fate was more or less inevitable, as my 12-year-old diet in the year 2000 consisted exclusively of Eggo waffles and repeat viewings of movies like Can't Hardly Wait on VHS. Aside from sharing basically all the same actors (LOL, Chris Owen, who are you, even), these films also all shared a knack for implanting a number of subliminal messages and lessons about what it means to be a human in the world — of both high school and beyond.
Below, the six films that shaped my worldview as a teen:
It goes without saying that allowing fictional characters to dictate one's nascent philosophical outlook is a very horrible idea, especially when you're gay (as I am) and closeted (as I was) and the movies are riddled with homophobic jokes and an astounding lack of diversity (which, let's be honest, they totally were).
But, well, shrug. Being a product of the '90s means having to accept that most everything you love from childhood is a de facto problematic fave.
While there once was a time when I watched all of these six films repeatedly, it recently occurred to me that it's been nearly 15 years since I've seen them. I was curious as to whether they would carry different messages or life lessons upon a second viewing, especially now that I'm in my late 20s.
Could it be that my cemented middle school impressions of them would change now that I'm an adult? Might I be able to find new meaning in these classic tales of love and deception? Would I still find value in the films' eternal lessons of self-acceptance and self-love and using humans as collateral in high-stakes bets?
Let's find out!
10 Things I Hate About You (1999)
Summary: A popular hot girl's father prohibits her from dating boys until her feminist misanthrope sister starts dating first. A boy who wants to date said hot girl hires another boy to take her feminist misanthrope sister out and melt her icy heart.
What I thought when I was 12: This classic retelling of Shakespeare's The Taming of the Shrew mostly taught me that even a frigid, heartless bitch like Julia Stiles' character Kat can find love and become happy. I filed it in the same mental category as the ending of How the Grinch Stole Christmas, which is to say I thought Kat was unquestioningly the villain of the movie.
Tween spirit animal: Julia Stiles' hot, popular sister Bianca, as played by the girl who previously played Alex Mack. Mostly because she was preoccupied with popularity and male attention, which, as a closeted youth, I found vaguely aspirational.
What I think at 27: Kat isn't nearly as much of a nightmare as I had previously thought; she was actually incredibly rational and everyone else at the school was a misogynistic nightmare. Like, Kat reads The Bell Jar and calls out the "oppressive patriarchal values that dictate our education" once, and then for the rest of the movie she is referred to as a "mutant," "insane head case" and "heinous bitch." At one point, a character accuses her of having PMS. Verona High is a lot like Twitter, actually.
Adult spirit animal: Ms. Perky, the guidance counselor who surreptitiously works on her erotic novel while meeting with students, which is basically me IRL.
American Pie (1999)
Summary: Four horny high school dudes obsessed with swiping their V-cards make a pact to do so by prom night; one of them fucks a homemade apple pie along the way.
What I thought when I was 12: Mostly, I watched this movie over and over out of pure sex curiosity, always paying particular attention to the Shannon Elizabeth topless scene in hopes that maybe it would make me straight (LOL). I also remember watching it pre-puberty and being like, "Wow, I can't wait to have a dick that fills out a sock as effectively as Jason Biggs' does."
Tween spirit animal: Finch, the guy who refused to ever take a shit anywhere but from the comfort of his own home. Until this movie, I had always thought I was the only one!
What I think at 27: This movie is actually a lot more nuanced and balanced than memory recalls. While the dudes are sex-crazed hornballs in the beginning, at the end they all come to the conclusion that there's actually a lot more to life than orgasms (friendship, love, etc.). This is a lesson that you learn when you hit adulthood, when you emerge from the jungle of teenage hormones and realize that it's actually important to like and respect the people you hook up with.
American Pie is also much more progressive, gender-wise, than I remembered. The men are concerned with giving their partners pleasure, to the point that one character procures a sex manual to learn how to go down on his girlfriend. Additionally, Heather (played by the delightful Mena Suvari) is a low-key bad bitch who demands respect from lacrosse player-cum-vocalist Oz. (Not to mention the fact that she flips the script on traditional gender roles by asking him to prom like it's NBD.) And let's not even talk about how perfect Michelle the band geek is, who straight-up uses James for sex on prom night, calling him a bitch in the process.
Adult spirit animal: You know what? Jason Biggs' dad, actually. For his clothing choices and dance moves, both of which deserve a resounding "it me."
Can't Hardly Wait (1998)
Summary: A bunch of high school kids go to a wild party on graduation night. One of them is an invisible unpopular guy harboring a stalkerish love for a newly single popular girl. Basically that's it.
What I thought when I was 12: Despite all the times I watched this, the only impression it ever really left is that Jennifer Love Hewitt is pretty. Oh, and also sometimes the geek gets the girl.
Tween spirit animal: Preston, the guy who was obsessed with JLH's character. I was similarly obsessed with my middle school (female) crush, who was also the most popular girl in school. I pretty much knew I was gay by then, but at the time I was still sorta like, "Maybe a beard will make all my problems go away!"
What I think at 27: This movie is weirdly bad but also slightly existential at the same time. There's a certain relatable quality about dorky Preston and his naive obsession with fate and "signs." He "harnesses his chi." He is unique and great.
Ultimately, this is a movie about the dangers of feeling validated by who we end up dating. Amanda gives a touching little soliloquy at the end about how her entire self-perception changed (for the better) when popular guy Mike Dexter wanted her, and the movie hints at her struggling to figure out her identity and self-esteem after he dumps her. Adults totally do this too! Except instead of at high school parties, it happens on Tinder and at dive bars.
(Also notable is that the film's ending promises bright futures to every non-popular person, while the nightmare popular crowd ends up being all losers, which is sometimes true IRL.)
Adult spirit animal: There is an angel stripper played by Jenna Elfman who shows up mid-film to give Preston a pep talk, and she truly is an angel (stripper). She has this very jaded-yet-still-somewhat-optimistic vibe that is so 20-something I could puke, but also: same.
Drive Me Crazy (1999)
Summary: Popular, status-obsessed busybody gives unpopular stoner dude a preppy makeover so they can go to a dance together.
What I thought when I was 12: This stood out as one of those "popularity isn't everything" movies where two characters from opposite sides of the popularity spectrum fall in love against the odds and realize how love transcends such labels. At the time, I basically looked at it as a sci-fi tale, because that shit would have never happened at my school (or probably any school).
Tween spirit animal: Melissa Joan Hart's character, who desperately wanted to be liked and popular and was weirdly straightforward about her desperate desire to be liked and popular. Which is so tween.
What I think at 27: A recurring theme while watching these movies is how weird it is that there are no gay characters (closeted or otherwise) at these schools. The best thing about Drive Me Crazy is that there's a background character who is quite obviously meant to be perceived as a real live-action gay. Granted, he's a gossipy queen who mostly just functions as a purse-like accessory to his popular girlfriends, but still: at least he exists!
More than any of the others so far, this is a movie about the human desire to be liked and coming to the realization that in the end, being a member of the "in crowd" doesn't matter. Then a video production geek puts together an epic film that shows how the popular kids are all brainless sheep who look ridiculous. It's all very similar to the infamous Fiona Apple "this world is bullshit" VMA speech of 1997, not to mention a valuable life lesson for any 2015 urban adult with a bad case of Instagram-induced FOMO.
Adult spirit animal: Dee Vine. She gets called "a once-fat bitch" during a fight with her misogynist douchebag boyfriend later on, so she fucks his face up with pepper spray! Queen.
She's All That (1999)
Summary: Popular jock bets his friend that he can turn any girl into the prom queen, even if she's an artsy outcast with glasses and a negative 'tude.
What I thought when I was 12: Its makeover-centric and "popularity isn't everything" themes made me view She's All That as the gender-reversed Drive Me Crazy. Worth noting is that I remember being very annoyed that an entire ensemble cast tried to pretend that very conventionally attractive young woman Rachael Leigh Cook (as Laney Boggs) was in fact not very conventionally attractive, all because she wore glasses and liked to paint.
Tween spirit animal: As a fat kid, I mostly identified with Laney's overweight friend Jesse, a minor character who I recall got very winded while running in a scene toward the end. I felt his cardiovascular pain.
What I think at 27: When you get past the unbelievability of the whole concept and also the grossness of how Zach (Freddie Prinze Jr.) repeatedly harasses Laney after she tells him to go away, it has a cute little message. This is a movie about feeling insecure and not fitting in.
Even when Laney starts having a little bit of confidence after her initial makeover, heartless she-devil Taylor comes along and calls her "vapor," thereby unraveling her and causing her to question her worth as a person. While it's easy to say "Oh, she shouldn't give a shit what people say/think," the movie is a reminder of the fact that all humans secretly feel a need to belong.
Adult spirit animal: The annoying guy who can't decide whether or not he wants to super-size his falafel balls, because the struggle of being an indecisive human is real.
Varsity Blues (1999)
Summary: A high school quarterback in a small Texas town struggles with who he wants to be versus who the town expects him to be.
What I thought when I was 12: The actual meaning of this film always eluded me. The main things I took away from it were: 1. James Van Der Beek gave a speech about dick euphemisms, 2. There was an infamous whipped cream bikini situation and 3. The football coach was kind of a monster.
Tween spirit animal: JVDB's character, because who isn't similarly obsessed with dicks and dick nicknames (dicknames!) as a little one?
What I think at 27: It's no wonder I didn't vibe with this movie as a tween; it's by far the most serious-minded on the list. It's a movie about power, success and succumbing to society's expectations. The football coach is a straight-up villain who pressures the players to do all kinds of dangerous shit (take steroids, play while injured) in order to squeeze out wins. In the adult world, this dude would be a total Miranda Priestly from The Devil Wears Prada: The nightmare boss who cares more about making a buck for the company than your own quality of life.
Also, there's this whole undercurrent of toxic masculinity in which Mox is shamed for being more into reading books than he is into playing football. Rewatching this, I was surprised it never spoke to me as a kid, considering how closeted I was. But at the end of the film, Mox decides to chase his academic dreams at Brown University rather than conform to what the town wanted of him, just as I eventually came out of the closet at the end of high school. Happy endings all around!
Adult spirit animal: Darcy. Sure, she is thirsty and opportunistic in her quest to only sleep with star quarterbacks, but she's also refreshingly honest and self-aware during her whipped cream bikini scene. I was kind of a Darcy in college. Weren't we all.