It’s Different When You’re Rich


I adore movies about high school. They’re like movies dreams: completely divorced from the thing that shares their name in real life, but still super fun to watch. Is there anything better than attractive mid-twenties B-Listers playing 18-year-olds enjoying social lives that I couldn’t even achieve in college? I think not. The idea that popularity is a cut-and-dry status and its own currency fascinates me to the point that I legitimately wish it were real. And when you add money and bad boys to the mix, it gets super freaky pretty quick. While I cannot recommend actually doing what I did and watching Heathers and Cruel Intentions back to back, I certainly wouldn’t stop you, either.



Director: Michael Lehman

Writer: Daniel Waters

Key Cast: Winona Ryder, Christian Slater, Shannen Doherty, Lisanne Falk, Kim Walker


In Short

Veronica, embroiled in the Heathers, a top-tier popular clique of wealthy mean girls all named Heather, finds an outsider boy named JD who understands her angsty high school frustrations. When they accidentally kill Heather #1, it sets off a string of murders that they dress as suicide attempts. After getting too far into JD’s scheme, Veronica tries to break up with him while still taking down Heather #3, who has risen to the top in Heather #1’s stead.


As Cinema

I feel obligated to start by saying, yes, there’s no way this cult classic could ever be remade today. It begins with a fake school shooting and ends with a near-miss school bombing. But taken for what it is, and when it’s from, it’s a dark, twisted little movie with a black heart and a big brain so that you can’t help but admire. Winona Ryder, the queen of teen angst, was the rare actual teen-ager in a teen movie, as she was only 17 upon its release. She gives a spot-on performance, at once relatable and nearly campy in its drama. She’s so typically teen-aged, giving the movie, no matter how weird it gets, a completely believable emotional core. And Christian Slater, like some sort of reptile, is creepy and cool at the same time as the damaged and murderous JD.


For as ridiculous as this movie’s plot gets, the writing is clever and subtle where it counts. Although the Heathers are never explicitly described as wealthy, it’s clear there’s an undercurrent of social class at play in the school’s social hierarchy. It’s why JD, the son of a very successful construction business owner, is able to weasel his way in in the first place. Although he’s odd, he’s right enough in what he can afford. It’s also why Betty, sweet and plane and inexperienced in croquet, fell out with Veronica. Their level of opportunity forced their paths to diverge. By never explicitly stating its rules, the movie can play with several different themes, culminating in a high school experience that feels as honest as it does bizarre.

The Horror

Although Heathers is usually referred to as a black comedy or satire, it also functions as a legitimate horror movie. There are monsters, both visible and hidden, and a hunter who has to answer the call and save her world.


As upsetting as it is to think about teenagers murdering one another and staging them as suicides, it’s not so far fetched when you’ve lived in the awful mind of a teenaged girl. Everything feels so extreme and important all the time, and it’s the first time that being a woman feels like an actual detriment rather than a simple fact. It’s pure chaos, and there’s no straightforward instruction manual for dealing with the new, fraught interpersonal relations. Even now, ten years out, I’m still petrified of being around teen girls. I know that life, and there’s nothing that would make me want to revisit it. I was legitimately shocked to find this written by a guy because it’s so accurate to how crazy been in high school made me — and clearly many others, given the staying power of this movie — feel.


The Heathers are a plague that has descended upon the school and cursed everyone with obsession. They are idolized and feared, but, as Veronica learns after Heather #1 dies and the school experiences a palpable sense of relief, they are not loved. They force a sense of competition between their fellow girls and even each other, something nobody asked for but with which they all comply.


But although the Heathers are the obvious beasties, a more insidious force permeates the entire film. These girls treat each other horribly for the dubious honor of going to college parties where they are set up with vulgar dudes who just want an easy lay. And although Veronica sees through it, she gets caught in a different web spun by the same type of spider with JD. He plays on her angst and into the fears created by her social situation, manipulating her into his own ends and becoming dangerous when she tries to stop him. Even in his final speech, bomb idiotically attached to his chest, JD tries to lay claim to Veronica’s autonomy, telling her how impressed he is with her, how special she is by his standards, even though she’s known from the get-go that she’s better than these high school shenanigans.


In the end, Veronica finally stands up for herself and for the dignity of her classmates. She chooses to be kind and sincere — the opposites of teen angst — without being a pushover. Like Van Helsing, she slays the beasts living among her and leeching off the lives of good people to create a less terrifying world.



Director: Roger Kumble

Writer: Roger Kumble

Key Cast: Ryan Phillippe, Sarah Michelle Gellar, Reese Witherspoon, Selma Blair, Joshua Jackson, Swoosie Kurtz, Christine Baranski


In Short

Sebastian and his stepsister Kathryn spend a lot of their time manipulating people into weird sexual scenarios for fun. After Sebastian sleeps with his therapist’s daughter and posts her pictures online, he tells Kathryn how bored he is, so the two formulate a bet: he will get the headmaster’s daughter, Annette, an avowed virgin until marriage, to sleep with him. If he can do it, Kathryn will have sex with him, and if he can’t, she gets his vintage Jaguar convertible. Meanwhile, Kathryn spends her time manipulating young Cecile, for whom her ex-boyfriend left her. Of course, as these bet-movies go, Sebastian falls for Annette and Kathryn gets angry. After Sebastian dies saving Annette from getting run over by a taxi, he leaves her with his journal, which contains all of his and Kathryn’s secrets. Kathryn is ruined just like she ruined everyone else.


As Cinema

Based on the 18th century French novel Les Liaisons Dangereuses, Cruel Intentions has a following, especially since it features 90s darling Sarah Michelle Gellar at the height of her Gellar-ness. But rewatching it proved quite dissatisfying. There’s so much plot that emotional beats get wholly shortchanged, making Kathryn’s dressing down at the end, an allegedly emotional moment, very hollow.


And on top of all that, Ryan Phillippe is the worst. He speaks with the sort of affectation that implies a bad American accent coming from a Brit, but that’s just him. It’s awful. The rest of the cast does their best to pick up his slack, and Selma Blair does a hero’s job of giving some semblance of depth to an utterly thankless role.

The Horror

I was hoping to glean something from this about the way we paint women as sluts and men as studs, but in this movie, the virgins win, the oversexed either die or lose everything, and poor Cecile gets hit and pushed to the floor a lot. In a straight drama, what’s supposed to come as a moment of comedic relief plays more like a running tragedy.


Kathryn’s desperation is interesting, especially when coupled with the throwaway lines at the beginning about the stepsiblings’ awful parents. Her mother is a trophy wife, and she feels she cannot live an honest life, so she makes others feel as miserable as she is. Sebastian is no different, but we’re expected only to care for one of them, and the movie never makes it clear why. It’s rather unfortunate, because I think there are decent points to be made about living truthfully and forgiving those we love for their pasts. But instead, we see only punishment. Cruel Intentions fails to understand what Heathers gets: teen angst is only effective entertainment because we, as an audience, know the light at the end of the tunnel that is adulthood.

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