• Fri, Dec 13 - 1:38 pm ET

Cruel Intentions Is The Most Messed Up Teen Movie Ever Made

cruel intentions fuck your brains out

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For every sleepover I went to in middle school, I think I watched Cruel Intentions twice. While that ratio sounds absurd now, it felt so incredibly normal at the time.After all, why wouldn’t we watch the greatest romantic thriller ever made on repeat? But now, looking back, I can’t help but wonder what in holy hell we were thinking. It’s not a great movie, it’s not even in the neighborhood of good. Unless, of course,  you judge your movies worth by the potential for incestual sex  scenes. And if that’s case, please leave this site and never look back. If that’s not the case and if you’re currently sitting around wondering why you too used to obsess over this horrible movie, then join me as we discuss it in depth.

Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillipee) are a step-brother and a step-sister who live together in a giant NYC apartment. Alone. There’s not a parent in sight. So don’t even try to find one. While there are teenagers who can be left alone and trusted to act like human beings, these are not two of them. No, these are two sociopaths. I would say sociopaths-in-training, but it’s clear within seconds that these two are far beyond that. And yes I’m talking about the bet.

Remember the bet? Sebastian wants to de-virginze the new school prude for sake of doing it. Her name’s Annette (Reese Witherspoon) and she’s the Taylor Swift of this story. By that I mean she’s blonde and gets off on thinking that she’s better than everyone. While she’s most definitely annoyingly pretentious, I do have a few ethical problems with someone attempting to seduce a high school girl in order to check it off his bucket list. But sure, let’s go with it. Why not?! Kathryn doesn’t believe he can do that. Mostly because he can’t even seduce her and she lives with him. So that’s where the bet comes in. For fun, let’s just go ahead and call it The Flowers in the Attic bet. If she’s right and he can’t succeed, he has to give her his Jaguar. If he succeeds — and this is where it gets really weird guys — she’ll let him have sex with her. I know they’re not biologically related, but COME ON. Can we all agree that’s a weird choice for a scriptwriter to make?

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  • Monty

    Yeah…whoever thought Dangerous Liaisons would be a good teen movie must have also been the same person who thought Notre-Dame de Paris would make an awesome kid movie because I cannot imagine those decisions were made independently of one another.

    Someone just likes adopting French literature in the most inappropriate ways possible.

  • Anon

    Clueless joined in on the step-sibling grossness. What makes it worse is he keeps calling cher’s dad dad, and her dad keeps referring to him as her brother.

    • Jenni

      Ew, I know. I never picked up on the problems with their relationship until I was older. But I still excuse it because Paul Rudd.

    • http://twilightirruption.blogspot.com/ abbeysbooks

      God you people are so funny and so clueless and so yesterday.

  • Maria McKee

    I love Dangerous Liaisons. And, I loved Cruel Intentions.

  • Jay Dee

    I was like 8 when I first watched this movie. Don’t ask me why an 8 year old was watching it; I shared a room with my older sister who liked to torture me by playing creepy/age-inappropriate movies at night because she knew I have slight insomnia and would not be able to sleep through them and would be forced to watch them. But that’s not the point, the point is this movie made 8-year old me cry. And not the way titanic made me cry. More like a creeped out “I don’t think I should be watching this” kind of crying. Needless to say I’ve never forgotten this movie. But despite the ridiculousness, for some strange reason, I actually love this movie…

    • http://twilightirruption.blogspot.com/ abbeysbooks

      Did you have a brother and a secret with your brother?

  • CrazyLogic

    …that movie is for teens? I thought it was for grownups, but about teens…

    • Jenni

      Blockbuster never stopped me from renting it on repeat in middle school.

  • BioChemGirl

    You forgot the most disturbing aspect of the bet. And I quote –

    Kathryn: “You can put it anywhere . . .”

    I don’t even have the words. BUT, I still completely love this movie. It’s one of my secret shames . . .

    • Jenni

      AHH I know! Who felt the need to write that line into the script?

  • Eileen

    It really isn’t incest – if it makes you feel any better, I distinctly remember Kathryn saying something to the effect of, “I’ll give you what you’ve wanted since our parents got married” – implying they’ve only been step-siblings for a couple of years, max. That’s not Flowers in the Attic-level incest. It’s not even ghostwritten V.C. Andrews-level incest.

    • Jenni

      It’s not technically incest…but still….you’re both very good-looking people who can clearly have sex with people aren’t in your family.

    • http://twilightirruption.blogspot.com/ abbeysbooks

      Let me explain through Lou Andreas Salome and Delauze: There was no such thing as incest UNTIL brothers got it in their heads that sisters could be turned into commodities and traded with other tribes – for other women – to form alliances between the two tribes. The FIRST incest prohibition was between brother and sister. The brother sho “deflowered” his sister rendered her unfit to be a commodity. In other words he wanted to keep her, not turn her into a poker chip to be traded. Cleopatra was the most cultured woman of her time, speaking all 12 or so dialects up and down the Nile, knowing all the exports, and a war strategist for Caesar and Antony. She was the daughter of a brother and sister, who were children of a brother and sister in their dynasty.

      Aren’t you glad Cleopatra’s parents didn’t find anyone not related who was attractive? You wouldn’t have that story to gossip over.

    • http://twilightirruption.blogspot.com/ abbeysbooks

      Correct. I knew a couple who were married whose parents had gotten married and were not related. They were very happy.

  • Mykonos

    This article is a bit pointless since they are not siblings. Anyways, I just have to say that I really love this movie. I’ve first seen it when I was 9 and it just fascinated me, I was obessed for a while, and I absolutely do not think I was too young to see it. Needless to say, it’s not the greatest movie of all time, but that’s not the point.

  • Meredith Hirt

    PLUS there’s the whole Cecile having an affair with her cello (or whatever) teacher who is not only older (in literal age and mentality age) but is also a different race and her mother can’t handle it. And Kathryn teaching Cecile how to make out while having a picnic in public.

  • Meredith Hirt

    PLUS there’s the whole Cecile having an affair with her cello (or whatever) teacher who is not only older (in literal age and mentality age) but is also a different race and her mother can’t handle it. And Kathryn teaching Cecile how to make out while having a picnic in public.

  • nwgsmom

    Definitely this movie made the whole thing super creepy and weird, but then consider Drive Me Crazy and CLueless in which the step siblings (or soon to be step siblings) end up together, making out, etc. and you are like Awwww!

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