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  • Alternative Character Interpretation:
    • Did Sebastian ever truly redeem himself? Will Kathryn now that her reputation has crumbled? 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 race, just about ANY parent would be furious to see their teenage daughter being seduced by a 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.
  • Best Known for the Fanservice:
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    • There's a lesbian kiss 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.
    • 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:
    • Let's just say this: Had a film concept like this been pitched in the 1930s, '40s, or much of the '50s, The Hays Code would have rejected it out of hand. For it not only features all three varieties of the "impure love" referred to in that document — incest, homosexuality, and miscegenation — but portrays the latter (mostly) positively. And a bunch of kids engaging in all this! Yet the soap-opera tenor of the piece manages to make it all delightfully funny. Of course, then it crosses the line a third time, and things get ugly.
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    • 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.
  • Crowning Music of Awesome:
    • 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.
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  • 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. But it helped skyrocket Sarah Michelle Gellar's career into the stratosphere, same with Reese Witherspoon, to say nothing as well about Ryan Phillipe.
  • Darkness-Induced Audience Apathy: 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."
  • 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.
  • Evil Is Cool: Kathryn and Sebastian.
  • Evil Is Sexy: Surprisingly averted quite a bit. Kathryn is certainly more alluring and overtly sexualized than the Nice Girl Annette... but only at first and even then in private. She explains that she needs to seem pure and nonsexual in public, to keep her reputation and maintain her private affairs. Once Annette becomes sexually active, she's very open about her sexuality, which may be why she's more popular from then on.
  • 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.
  • Hilarious in Hindsight:
    • Fans of Buffy might be a bit disturbed at seeing the actress play a mega bitch, until we get to the final two seasons. Made better considering Sarah Michelle Gellar auditioned for the role of Cordelia initially, making this a window into what she could have done with that role instead.
    • Kathryn laments that she has to act like "Mary Sunshine" all the time. 3 years later, a supporting actress in this film, Christine Baranski, would play that part in Chicago.
    • Reese Witherspoon's boyfriend Trevor is said to be backpacking around Europe. Years later, Witherspoon goes on her own backpacking adventure.
    • Annette and Cecile's relationship becomes funny when you consider they were rivals turned friends in LegallyBlonde
  • 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.
  • 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.
  • 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 naive Cecile is, and how much Sebastian and Kathryn are taking advantage of her.
  • Sequelitis: A prequel, then a sequel. Cruel Intentions 2 is 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.
  • Some Anvils Need to Be Dropped: Kathryn's Freudian Excuse Motive Rant about society's double standards toward women in comparison to men in regards to sex.
  • Strawman Has a Point: While Cecile's mom may have been racist against Ronald, she still brought up a good point about how she helped him out by hiring him while he repays her by romancing her daughter. From her point of view, she genuinely saw it as a stab in the back that he would do something like that and she felt taken advantage of as a result. Plus, even if the race factor were removed, the fact remains that Cecile was a young teenage girl still in high school while Ronald, as her music teacher, appeared to be older than high school age, considering how he was qualified enough to be a music instructor. Plus, it really didn't help Ronald's case that he was trying to have sex with Kathryn despite supposedly being in love with Cecile, making Cecile's mom look like she was right in retrospect to be wary of Ronald being around her daughter.
  • Tear Jerker:
  • Technology Marches On: Invoked when Cecile and Ronald send letters to each other and when Ronald suggests emailing Cecile, Sebastian responds that "emails are for geeks and pedophiles".
  • 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, even congratulating Blaine at one point for having an active sex life.
    • Similarly, Sebastian is supposed to be more sympathetic and likable than his literary counterpart, but that his act of sex toward Cecile still qualifies as rape, and that society has become more of 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.

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