* AlternativeCharacterInterpretation: Did Sebastian ever ''truly'' redeem himself? Will Kathryn now that her reputation has crumbled? Has Annette gone [[FaceHeelTurn 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 has 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 HeelFaceTurn 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.
* BestKnownForTheFanservice: There's a lesbian kiss in the first movie. That's what most people know about it.
** There's a lesbian kiss [[ShowerScene in a shower]] (between [[{{Twincest}} twins]], no less) in the prequel. That's all that ''anyone'' knows about it.
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%% Bring CompleteMonster examples to this thread before adding any: http://tvtropes.org/pmwiki/posts.php?discussion=6vic3f9h1cy5qivsenw8llok&page=1. Check the FAQ first to see what would qualify characters for the trope, and if there has been previous discussion on the work.
* CrossesTheLineTwice: Let's just say this: Had a film concept like this been pitched in the 1930s, '40s, or much of the '50s, the HaysCode 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'' [[ThinkOfTheChildren a bunch of kids engaging in all this]]! Yet the [[{{Camp}} soap-opera tenor]] of the piece manages to make it all delightfully funny. [[spoiler: Of course, then it crosses the line a ''third'' time, and things get ugly.]]
%%
* [[SugarWiki/AwesomeMusic Crowning Music of Awesome]]: The soundtrack includes some of the best musicians of TheNineties: Music/{{Placebo}}, Music/AimeeMann, Music/SkunkAnansie, Music/{{Blur}}, and Music/TheVerve
* CryForTheDevil: [[spoiler: 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 Anette 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. As she stands in shock, the school's headmaster comes up behind her and detaches the crucifix from her necklace....causing a trail of cocaine to spill out. This prompts tears of shame from Kathryn to end the movie on a sad note. Though granted, [[KickTheSonOfABitch she had it coming.]] ]]
%%* CultClassic
* DarknessInducedAudienceApathy: By the end of the film no one has really done anything heroic except for [[spoiler: Sebastian, and he's dead]]. And nobody looks all that happy, either - not even the characters who "won."
* DracoInLeatherPants:
** Sebastian and Kathryn for quite a good number of viewers. Though some will cheer them on [[RootingForTheEmpire 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.
* EvilIsCool: Kathryn and Sebastian.
* HilariousInHindsight: Fans of Series/{{Buffy|The Vampire Slayer}} 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 ''{{Film/Chicago}}''.
* JerkassWoobie: 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'' [[CryForTheDevil end of the film.]]
* LesYay: 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.
* MagnificentBastard: Sebastian and Kathryn try for this, but things [[LoveRedeems fall]] [[SmugSnake apart]] for them both.
* {{Narm}}: The characters all acting exactly like their situation is as important as in the original ''Dangerous Liasons'', despite being mostly meaningless high school flings.
* NeverLiveItDown: [[spoiler: 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.
* OldShame: Creator/AmyAdams can't feel good about having ''Cruel Intentions 2'' on her resume.
* PlayingAgainstType:
** [[Series/BuffyTheVampireSlayer Buffy Summers]] plays Kathryn. Unless you knew her as [[Series/AllMyChildren Kendall]] first, in which case it's returning to type.
** Pacey Witter from Series/DawsonsCreek playing CampGay Blaine.
* {{Sequelitis}}: Both sequels, with the third one being InNameOnly sequel. ''Cruel Intentions 2'' though has a dubious distinction of [[PoorlyDisguisedPilot originally being a failed 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) / stealth 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 downer ending (the Annette stand-in turns out to be an evil bitch friend of Kathyrn, designed to break Sebastian and drive him to the dark side) and gratuitous nudity scenes inserted into the film as it was released direct to DVD.
* SomeAnvilsNeedToBeDropped: Kathryn's FreudianExcuse MotiveRant about society's [[DoubleStandard double standards]] toward women in comparison to men in regards to sex.
* StrawmanHasAPoint: 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 Cecil's mom look like she was right in retrospect to be wary of Ronald being around her daughter.
* TearJerker: [[spoiler: Sebastian's RedemptionEqualsDeath, especially since [[DiedInYourArmsTonight he dies in Annette's arms]].]]
** Also, [[spoiler: Kathryn's [[CryForTheDevil defeat]], though deserved, is still sad due to her [[TearsOfRemorse reaction]]. Even one of the people in the filmmakers' DVD commentary calls the scene "so heart-wrenching."]]
* TwoDecadesBehind: Okay, so this is based on an 18th-century French novel. But it obviously takes place in the modern day (late 1990s) given [[SorryILeftTheBGMOn the music heard on the (in-universe) soundtrack]] and the technology present, which makes the elitist and borderline reclusive behavior of the upper-class characters - not commonly seen in American society since the mid-1950s or so - come off as slightly anachronistic. Not to mention Mrs. Caldwell's [[MalignedMixedMarriage disgust at race-mixing]], which is especially out of character for a sophisticated New Yorker in the late twentieth century.
* ValuesDissonance: As pointed out by WebVideo/NeedsMoreGay, 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.
** Similarly, he points out that 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.