* AlternativeCharacterInterpretation: Did Sebastian ever ''truly'' redeem himself? Will Kathryn now that her reputation has crumbled? Has Annette gone [[FaceHeelTurn the OTHER direction?]]
* 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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* [[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 DownerEnding.]]
* 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 and [[EvilIsSexy Sexy]]: 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.
** 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.]]
* [[HoYay 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.
* 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.
* 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.
** And [[JoshuaJackson Pacey Witter]] from DawsonsCreek playing CampGay DeadpanSnarker 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.
* 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."]]