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  • Adaptation Displacement: The film has gone on to become much more famous and popular than the 18th century novel it was originally based on. Even now, few people know Cruel Intentions is just a modernized remake of an old French novel written centuries ago.
  • Alternative Character Interpretation:
    • Did Sebastian ever truly redeem himself?
    • Will Kathryn redeem herself now that her reputation has crumbled, and her tears are ones of remorse and shame? Or is she upset about getting caught?
    • Has Annette gone the OTHER direction?
    • Cecile comes off as almost disturbingly childish in some scenes, acting more like a six year old than a teenager. Is she merely extremely smothered, repressed, or does she have some kind of learning difficulty?
    • Mrs. Caldwell. Racist elitist snob or concerned mother who truly did want to protect her daughter and other young girls from being taken advantage of by cads like Sebastian and older men like Ronald? While not the most pleasant character in the film, she was actually the one who warned Annette about Sebastian's womanizing ways and, regardless of ethnicity, just about any parent would be furious to find out their teenage daughter was being seduced by her music teacher. It didn't help Sebastian's case that until his Heel–Face Turn where he genuinely fell in love with Annette, he was every bit the manipulative bastard Mrs. Caldwell thought he was. It really didn't help Ronald's case that as Cecile's music teacher, he was very likely older than her, in addition to the fact that despite supposedly being in love with Cecile, Ronald really didn't seem to mind going bed-hopping with other girls like Kathryn.
    • Toward the end of the film when Kathryn tells Ronald that Sebastian had hit her, the actual scene of Sebastian striking her was filmed, but it was deleted because the dialogue from Sebastian during this part didn't fit his character, and the writers decided to let the audience decide for themselves whether he actually did hit Kathryn, or she made it up.
  • Awesome Music:
    • The soundtrack includes some of the best musicians of The '90s: Placebo, Aimee Mann, Skunk Anansie, Blur, and The Verve.
      • ESPECIALLY The Verve's "Bitter Sweet Symphony", as the song that played over the ending of the film.
    • The Jukebox Musical's soundtrack ain't bad, either.
      • Kathryn's actress in particular has some serious pipes — just look up the show's "Only Happy When It Rains" or "Kathryn's Turn Medley" and listen to her utterly kill it.
      • As giggle-inducing as the show's version of "I Want It That Way" is, it's actually a very nice arrangement of the song.
      • "Colorblind" is a remarkably beautiful track, as well as a genuinely sweet moment.
  • Best Known for the Fanservice:
    • There's a 45 second lesbian kiss between Sarah Michelle Gellar and Selma Blair's characters in the first movie. That's what most people know about it. People even paid close enough attention that it’s a bit notorious that, contrary to Kathryn’s instructions, Cecile is the one who sticks her tongue out.
      • Gellar and Blair even spoofed it 21 years later at the MTV Movie Awards, trying to recreate the scene only to smack their lips into the glass wall between them due to the COVID-19 pandemic.
      • The kissing scene between Sarah Michelle Gellar and Selma Blair ranked the film at #32 on Entertainment Weekly's "The 50 Sexiest Movies Ever" (issue #1023, November 28, 2008) and at #2 on Channel 4's "100 Greatest Sexy Moments".
    • There's a lesbian kiss in a shower (between twins, no less) in the prequel. That's all that anyone knows about it.
  • Broken Base: The Sebastian/Kathryn ship is hotly debated in the fandom. While everyone seems to agree it's more interesting than Sebastian/Annette, the sentiment towards the relationship is either absolutely loving it, or, "Ewwwwwwwww!"
  • Crosses the Line Twice: The musical manages to do this to Mrs. Caldwell's bigotry. Blatant racism? Not funny. Blatant racism set to the tune of a middle aged white lady singing "No Scrubs"? Too hysterical for words.
  • Cry for the Devil: Annette knows that Kathryn is ultimately responsible for Sebastian's death through what she read in Sebastian's journal. Many photocopies of it are then made and Annette gets Cecile to distribute it to the other students at school. Kathryn is delivering a eulogy for Sebastian in the chapel when someone enters the church and quietly lets the higher-ups know what is going on. Everyone begins to exit the chapel, prompting an outraged rant from the normally composed Kathryn. She storms out, demanding an explanation....and soon comes to realize that everyone now knows the whole truth about her.
  • Cult Classic: And how. The film garnered mixed reviews but did garner a box office hit. It also helped skyrocket Sarah Michelle Gellar's career into the stratosphere, same with Reese Witherspoon, to say nothing as well about Ryan Phillipe.
  • Diagnosed by the Audience:
    • It’s been theorised that Kathryn might have a Borderline Personality Disorder.
    • Cecile is implied to have some sort of mental disorder, coming from her immature behavior and childish style of clothing. She even has to be reminded that she needs to keep her legs closed while sitting down in a short skirt. Mentally she comes across as being about six years old.
  • Draco in Leather Pants:
    • Sebastian and Kathryn for quite a good number of viewers. Though some will cheer them on even knowing what evil bastards they are.
    • Cruel Intentions 2 actually treats Sebastian this way in-film, with Kathryn being blamed as the reason he became evil to begin with.
  • Dyeing for Your Art: Sarah Michelle Gellar, who was most famous for portraying Blonde Buffy Summers at the time, dyed her hair Brunette to show how different Kathryn is to Buffy.
  • Evil Is Cool: Kathryn and Sebastian.
  • Fan-Preferred Couple: There are very few fanfics for the canonical pairing of Sebastian/Annette around the internet. Most fans were rooting for Sebastian to end up with his scheming stepsister Kathryn, due to the main instigating force being them making the bet, which involves Kathryn letting him sleep with her, and Kathryn getting the Draco in Leather Pants treatment due to being played by Sarah Michelle Gellar.
  • Heartwarming Moments: The musical's version of "Colorblind" by Counting Crows, reworked as a love duet between Sebastian and Annette just before Their First Time. In a show full of debauchery and Crosses the Line Twice, this stands out as a simple, honest expression of love, and it's really very touching.
    I am ready, I am ready, I am ready, I am... fine.
  • Jerkass Woobie: Sebastian becomes this at about the 2/3 point in the movie when he realizes that he does love Annette, and Kathryn may also qualify at the very end of the film.
  • Les Yay: Kathryn and Cecile, in a creepy, manipulative way on Kathryn's part. There was also Kathryn and Annette in the original ending, in a creepy, manipulative way on Annette's part.
    • In the prequel, two women (a pair of twins) share a kiss and shower together as the male protagonist watches.
  • Narm: The characters all acting exactly like their situation is as important as in the original Dangerous Liaisons, despite being mostly meaningless high school flings.
  • Narm Charm: The musical basically runs on this. The creators apparently knew they were adapting a piece of beloved schlock, and decided to lean into it — and, amazingly, it kind of works.
  • Never Live It Down: Ronald basically killed Sebastian, at least how fans see it. Though, given how the French novel that Cruel Intentions was based on went down, it really couldn't have ended any other way.
  • Nightmare Fuel:
    • Sebastian first time taking advantage of the drunken Cecile. Sure, it's Played for Laughs, but many people with a mental disability have been taken advantage of in such a way by people they've trusted.
    • How does Sebastian attempt to get Annette to give up her virginity to him? Through gaslighting and emotional manipulation. The worst part is, it almost works.
  • No Yay:
    • Sebastian/Kathryn is this to those that find the Flirty Stepsiblings aspect too gross to get past.
    • Sebastian/Cecile, and Kathryn/Cecile, given how dumb and naïve Cecile is, and how much Sebastian and Kathryn are taking advantage of her.
  • Sequelitis: A prequel, then a sequel. Cruel Intentions 2 was originally intended as a pilot (killed by religious groups, when they found out that the pilot, called "Manchester Prep", featured a scene where a Cecile expy learns about how to orgasm while riding a horse) of a reboot set shortly after Sebastian and Kathyrn's parents married and the two becoming allies and featured stand-in characters for Cecile and Annette. When the pilot was ultimately rejected, the film was given a new, more conclusive ending (the Annette stand-in turns out to be one of Kathyrn's lovers, set up to start a romance with Sebastian and seduce him to the dark side so that Kathryn could have a threesome) and gratuitous nudity inserted throughout the film as it was released direct to DVD. The sequel is about Kathryn and Sebastian's suspiciously similar cousins, actual siblings this time, running very similar seductions.
  • Squick: The sexual relationship between step-siblings Sebastian and Kathryn in the first film.
  • Strawman Has a Point: The story's narrative portrays Mrs. Caldwell as being in the wrong for standing against Ronald and Cecile being together, and she's mentioned a few times as being a bigoted racist. But even with all that, she wasn't wrong in saying she was the one who hired Ronald to be Cecile's music instructor (even if she did say it in a very tone-deaf and ignorant way). Thus as a parent, she had every right to be furious that the man she hired was trying to romance her daughter. And as an employer, she had every right to fire Ronald for what she personally saw as him taking advantage of her and breaking her trust. Considering some of Ronald's personal failings that get exposed later on (with him trying to sleep with Kathryn despite supposedly being in love with Cecile, and being so hot headed that he gets into a fight with Sebastian that ends in his death), Mrs. Caldwell can come off as being much more right than wrong in her stance to not let Ronald be around her daughter, even if she was doing it for wrong, narrow-minded reasons.
  • Tear Jerker:
  • Too Bleak, Stopped Caring: By the end of the film no one has really done anything heroic except for Sebastian, and he's dead. And nobody looks all that happy, either — not even the characters who "won."
  • Unintentional Period Piece: It obviously takes place in the late 1990s given the music heard on the (in-universe) soundtrack and the technology present— these days Cecile would probably scan Sebastian's journal and upload it to any and all social media she and her circle of friends use.
  • Values Dissonance:
    • As pointed out by Needs More Gay, the film was released in that weird transitory period where it's very hard to tell if the homophobic lines from certain characters are supposed to make them look bad, or are just something considered more acceptable at the time. Though, considering how the issue of LGBT rights wouldn't completely gain more traction until the early to mid 2000s, it's more likely that Sebastian's gay slurs were simply a reflection of the 1990s, an era where homosexuality was much less acceptable than it is now. Notably, despite regularly using homophobic slurs, he never actually seems to be against the idea of homosexuality itself, even congratulating Blaine at one point for having an active sex life; it's clear that the gay slurs were used simply to emphasize the characters' viciousness and would definitely not have been considered acceptable language at the very least. (Just imagine Kathryn saying "Trevor's a fag" in front of anyone but Sebastian.) The only difference between now and then is that Sebastian might have less leverage with which to blackmail Greg in today's culture. It's fairly certain Sebastian couldn't care less that Greg was gay, as he's obviously friends (or as much as he is with anyone) with the very out-of-the-closet Blaine; he simply found a weakness that he could easily exploit for his own gains.
    • Similarly, Sebastian is supposed to be more sympathetic and likable than his literary counterpart, but his act of sex toward Cecile still qualifies as rape, and society has become more acknowledging of this in the past fifteen years.
    • Sebastian's Establishing Character Moment of taking nude pictures of his therapist's daughter and posting them on the internet for shits and giggles is Played for Laughs as him getting one over on his therapist. Nowadays, in the wake of Amanda Todd, Tyler Clementi and overall awareness of the impact revenge porn has on its victims Sebastian's prank would be widely viewed as morally reprehensible and outright illegal.
    • The ending of the film hinges on the audience accepting that Sebastian, though a bad person, redeemed himself before his death and Kathryn receiving Laser-Guided Karma for her actions. However, while at the time it would be hard to argue she was any worse then him, nowadays with more reflection and better understanding of sexual consent and Slut-Shaming, Sebastian commits far worse crimes than she ever did (though she's a Manipulative Bitch, she never commits sexual assault, and Sebastian out-right seduces women solely to ruin their reputations), and his "redemption" amounts to realising he genuinely loves Annette, yet this love doesn't stop him continuing to still treat her terribly. With how he's a sexual predator who's only saving grace is a Morality Pet he kicks, while Kathryn is merely an Alpha Bitch with a Freudian Excuse, he's still far worse than her. It comes off as Black-and-Gray Morality while expecting the audience sympathy to lie with the black side.
  • Values Resonance: For all the horrible things she does, Kathryn's rant about how Sebastian can sleep around all he wants and the worst he'll get is some finger-wagging, while she would be all but burned at the stake for being as sexually confident and forthright as he is, is just as true today as it was then, if not more so. It's not unusual for many people to use the internet to "slut-shame" women, as even the accusation, regardless of it's veracity, can have lasting consequences.

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