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[[quoteright:250:http://static.tvtropes.org/pmwiki/pub/images/cruelintentions_9451.jpg]]

->''How can someone so charming be so manipulative?''
-->--'''Annette'''

''Cruel Intentions'' is a 1999 American drama film written and directed by Roger Kumble. The movie is a comedic and dramatic appropriation of the 18th-century French epistolary novel ''[[Literature/DangerousLiaisons Les Liaisons Dangereuses]]'' by Laclos, but unlike other modern film versions of the novel (''Literature/DangerousLiaisons'') is not set in the France of that time.

The story follows a handful of wealthy teenagers living in modern New York City. The plot is mainly driven by a bet held between the two main characters, and it heavily involves manipulation, seduction, and love in a rich and sophisticated socially elite youth atmosphere.

The film started as an independent film with a much smaller budget, and was later picked up by Columbia Pictures. The film was released on March 5, 1999. It was later followed by two direct-to-video films: a prequel, ''Cruel Intentions 2'', and a sequel, ''Cruel Intentions 3''. A pilot for a sequel television series set 15 years later is currently being filmed, with Gellar returning to the role of Kathryn.
----
!!Tropes associated with this work:

* AbusiveParents: Despite Kathryn's impressive academic record and leadership roles as well as her talents at piano, foreign languages and English vocabulary, her [[ThePerfectionist perfectionist]] mother constantly reminds her daughter what a disappointment she is for failing to live up to her impossibly high expectations.
* AdaptationalHeroism: Sebastian is presented far more sympathetically than his counterpart in the original novel and its adaptations.
* AdultsAreUseless: The teenagers run the show and use their elders as pawns. In the second film, Kathryn and Sebastian's parents are essentially middle-aged versions of their children respectively. Responsible authority figures apparently don't exist in this universe.
* AgeInappropriateDress: Despite only being in high school, Sebastian and Kathryn wear power suits as loungewear. Although, for the Upper East Side in New York City, this is more or less TruthInTelevision. And let's not even get started on Kathryn's lingerie as daywear.
* AgeLift: Kathryn and Sebastian's counterparts in the novel were in their 40s but are now around seventeen.
* AGlassOfChianti: Kathryn holds a [[WineIsClassy glass of champagne]] while EvilGloating.
* AlcoholicParent: Kathryn refers to Sebastian's "impotent, alcoholic father" in the first film, and in the second, his mother is said to be "in rehab for the long haul," hence the reason why he moves in with his father.
* AllGirlsLikePonies: The second movie uses a racy version of this trope where proper horse-riding technique is used as a metaphor for sex.
* AllGirlsWantBadBoys: Sebastian's main charm seems to be that he is "bad boy," which ultimately works on Annette.
* AlphaBitch: Deconstructed with Kathryn. She ''is'' the most popular girl in school and regularly abuses the privilege, but she is also a [[LonelyRichKid borderline recluse]] much of the time and confesses to Sebastian that [[FreudianExcuse she isn't really happy with her life.]] Honestly, her desire to want to humiliate other girls is more out of envy than pure sadism.
* AmIJustAToyToYou: Inverted. Sebastian tells [[spoiler: Annette]] that she was this when he breaks up with her. She doesn't believe him, because he is visibly trembling and miserable as he says it, but still finds it too painful to stay with him.
* AndNowForSomethingCompletelyDifferent: Watching it today, it's clear that ''Cruel Intentions'' is far and away from the typical cheesy teen-pop fare that was common in Hollywood in the late 1990s and early 2000s, [[UnbuiltTrope though ironically it preceded most of the films it's being compared to here]].
* ArchnemesisDad: Edward Valmont and his son Sebastian have a strained relationship even though [[LikeFatherLikeSon they're exactly the same]].
* ArmouredClosetGay: Annette's friend Greg plays on the football team and makes himself out to be a heterosexual jock type. Of course he isn't, which is taken advantage of by Sebastian.
* AsYouKnow: For some reason (i.e., exposition), Kathryn has to remind her stepbrother not only who her ex-boyfriend is, but also that he just dumped her, like, last weekend.
** Also, this awkward exchange:
-->'''Sebastian''': Nice to see you agan, Mrs. Caldwell!
-->'''Mrs. Caldwell''': You remember my daughter, Cecile.
* BatmanColdOpen: Sebastian's session with the psychologist to deal with his "sexual addiction." This also serves as his EstablishingCharacterMoment, where he comes onto his doctor who, after he leaves, receives a phone call from her crying daughter telling her that Sebastian seduced her and let him take nude photos of her that he posts on the internet. Game, set, match.
* BeAWhoreToGetYourMan: Kathryn literally tells Cecile to do this.
* TheBet: The whole plot revolves around a bet two step siblings make. Kathryn promises she will sleep with Sebastian only if he manages to sleep with Annette (the headmaster's daughter) before school begins. Sebastian ends up falling in love with Annette instead.
* BettyAndVeronica: Sebastian must choose between his affections for the sweet, blonde Annette and the cruel, dark-haired Kathryn. This is reversed in the prequel where Kathryn is an icy blonde and [[SuspiciouslySimilarSubstitute Danielle]] is a warm brunette and then [[spoiler: subverted in the plot twist at the end when Danielle reveals that she's really just like Kathryn.]]
* BitchInSheepsClothing: Kathryn's M.O. is to befriend her naive classmates and take them under her wing so she can subtly be a [[ToxicFriendInfluence bad influence]] on them.
* BittersweetEnding: [[spoiler: Kathryn gets her comeuppance in the end, but Sebastian dies, both Annette and Cecile seem to have become more corrupted from the experience, and even Kathryn's defeat (set to The Verve's "Bittersweet Symphony") [[CryForTheDevil isn't pleasant.]] It's more bittersweet if you choose to be hopeful about all three girls' futures, so it's all up to the audience to decide in the end.]]
* BlackComedyRape Sebastian essentially date rapes Cecile by first getting her UnsuspectinglySoused and then using coercion to make her relent to him performing sex acts on her. And it's PlayedForLaughs the whole time.
** Hell, if Sebastian's {{Wangst}}ing and the [[CerebusSyndrome tragic climax]] and [[Main/{{Melodrama}} denouement]] were edited out, the whole film could pass for a BlackComedy. The opening scene alone is a comedic masterpiece.
** Subverted in ''Cruel Intentions 3'', in which there's an [[RapeIsASpecialKindOfEvil awfully disturbing]] [[RapeAsDrama full-on rape]].
* BoardingSchool: Technically, Manchester Prep is a day school, but it comes with the same tropes of spoiled students picking on {{Scholarship Student}}s and engaging in SituationalSexuality -- except for the one perfect and kind student, of course.
* BookEnds: The opening scene is the same as the last scene, except with [[spoiler: Annette replacing Sebastian. In the original ending, this made ''much'' more sense given the state of Annette's character alignment.]]
* BrainyBrunette: The calculating, devious Kathryn.
* BrotherSisterTeam: The manipulative Kathryn Merteuil and Sebastian Valmont are step-siblings - and yes, [[BrotherSisterIncest that particular loophole is milked for all it's worth]].
%%* ButtMonkey:
%%** Cecile in the first movie.
%%** Cherie in the second.
* TheCakeIsALie: [[spoiler:When Sebastian comes to collect from Kathryn, she just laughs in his face and gives him a ReasonYouSuckSpeech]]. Unusually for this trope, there is no indication that it was a lie from the start, and it seems like [[spoiler: Kathryn intended to keep her end of the deal until she realised Sebastian had truly fallen for Annette and got jealous.]]
* CameraFiend: Sebastian seducers the psychiatrists daughter by taking pictures of her legs- later, he's seen photographing a blithely ignorant Cecile.
* CampGay: You can tell Blaine is a DepravedHomosexual because his dye job matches his sweater vest -- it doesn't get much campier than that. Also, he displays mannerisms that are stereotypically associated with gay men.
* CantHoldHisLiquor: Cecile gets pretty tipsy off one Long Island Iced Tea.
* CasualCarGiveaway: Either this trope or HeroStoleMyBike is the only plausible explanation for that bizarre closing shot of Annette [[spoiler:driving off into the desert behind the wheel of Sebastian's prized vintage Jag]].
* CatholicSchoolGirlsRule: Though their uniforms are more drab and conservative than is popularly portrayed.
* ChekhovsGun: [[spoiler:Sebastian's journal. He's seen with it throughout the film writing or inserting pictures. He later delivers it to Annette for her to read in order to wipe his slate clean. After Sebastian's untimely death due to Kathryn's manipulation, Annette does something else with it. See Cry For The Devil below.]]
* ChineseLaborer: Technically, Kathryn's handmaiden is Vietnamese. In the prequel, she has another one who's a Cambodian refugee, but she's mistaken for Chinese and Japanese by her mistress.
* TheCobblersChildrenHaveNoShoes: The psychiatrist is about to go on a book tour to promote her ''Great Parenting'' manual, however when she finds out her daughter was manipulated and had nude photos of herself put on the internet, her response is neither kind nor particularly constructive.
* ColdHam: One of the pleasures of watching this film has to be watching and listening to Gellar [[ChewingTheScenery take frequent bites out of the tony surroundings]] - dainty bites, to be sure, but all the more memorable precisely because of that. And most of them in the same [[Series/BuffyTheVampireSlayer cynical California cheerleader]] voice she made famous.
* ColorCodedForYourConvenience: Sebastian and Kathryn wear black and other dark colors, while Annette prefers white and pastels. Cecile initially wears white and other light colours, but shifts to wearing red as Kathryn and Sebastian begin to corrupt her.
* ConsummateLiar: Kathryn, Sebastian. Annette's best friend, Greg, qualifies as well.
* CoolCar: Sebastian's Jaguar, which Kathryn has her eye on. In the end, [[spoiler: Annette drives it off into the sunset after exposing Kathryn Sebastian's funeral.]]
* CoolOldLady: In the original story, Madame de Rosemonde becomes a trusted friend and wise mentor to Madame de Tourvel, but in this version, Sebastian's Aunt Helen is just an eccentric biddy who whips up iced tea ([[UnsuspectinglySoused wink]]) and pawns her charity duties off on her nephew and his girlfriend so she can go to the theater instead.
* CorruptTheCutie: Kathryn makes it her mission to turn her ex's new girlfriend Cecile into the "premiere tramp of the New York area" and enlists Sebastian's help. Meanwhile, Sebastian's summer project is to conquer the headmaster's daughter Annette's IncorruptiblePurePureness.
* CoveredInMud: In the second film, Sebastian pushes Kathryn in a pool of mud as a declaration of war.
%%* DeadpanSnarker: Sebastian and Kathryn both have mastered the art form.
* DarkerAndEdgier: Of all the ''Les Liaisons Dangereuses'' adaptations, this modern version is definitely the edgiest and also arguably the darkest in the way that Kathryn Merteuil and Sebastian Valmont come across as even more [[TheCynic brooding]], [[StrawNihilist nihilistic]] and [[TheMasochismTango emotionally disturbed]] than their [[SophisticatedAsHell 18th-century]] [[Main/{{Narcissist}} counterparts]]. Add the fact that all the characters are [[JailBait minors]], and you've got an especially disturbing tale of [[HornyDevils sexual predation]] and [[TeenageWasteland death]].
* DefiantCaptive: Cecile comes off as [[NotAfraidOfYouAnymore surprisingly tough]] when Sebastian is performing cunnilingus on her against her will. She merely glares and acts annoyed, only breaking down after Sebastian leaves.
* DepravedBisexual: Kathryn doesn't necessarily identify as bisexual per se, but that doesn't stop her from convincing Cecile that it would be a good educational experience to "practice" the art of making out on each other to test her inhibitions.
* DepravedHomosexual: Blaine, who's openly gay, is eager to help Sebastian blackmail closeted Greg by getting him into bed so that Sebastian can walk in on the two men together and take photos of them in a compromising position. To be fair, the heterosexual characters are also depraved, so subverted.
* DisappearedDad: It's unknown who or where Kathryn's biological father is.
* DivergentCharacterEvolution: [[spoiler: An inverted example. In the prequel Sebastian is kind and considerate, and Kathryn is cold, calculating, and uses sex as a weapon; and frequently destroys other peoples lives for her own amusement or revenge. Both try to convert the other to their way of thinking, but Sebastian is broken by Kathryn and ends up becoming a male version of Kathryn.]]
* DivingSave: [[spoiler: Sebastian does this to save Annette from an oncoming taxi]].
* TheDogBitesBack: [[spoiler: Cecile is the one that photocopied the journals. And to further add salt to the wound, she personally hands one to Kathryn.]]
* DramaticShattering: Kathryn flies into a rage when Sebastian doesn't want to fuck her anymore and throws a [[AGlassOfChianti wine glass]] at him, shattering against her bedroom door as he shuts it behind him on the way out.
* EthnicMenialLabor: [[InJoke Margarita found this trope while she was cleaning]]. The series loves using this trope for comedic effect: The Caldwells have a Hispanic maid, while the Valmonts have two different [[ChineseLaborer Asian maids]] who give pedicures, an [[TheJeeves English butler]], a [[CreepyHousekeeper creepy]] [[GratuitousGerman German]] chef, an Arab driver who wears a turban and two [[http://tvtropes.org/pmwiki/discussion.php?id=r333xdlyhlgw1bmg4r9cer31 Swedish masseuses]]. There's also a [[AsianSpeekeeEngrish Japanese sushi chef]] at school. Of course, all their personalities are [[FunnyForeigner stereotypical and over-the-top]].
* EvilGloating: Kathryn sure loves doing this. Half her lines consist of it.
* EvilMatriarch: Tiffany Merteuil shows her "love" for her family by being [[MyBelovedSmother controlling]] and [[ManipulativeBastard manipulative]].
* EvilTastesGood: Kathryn basically says this in one scene.
* {{Expy}}:
** Sebastian Valmont is Vicomte de Valmont.
** Kathryn Merteuil is Marquise de Merteuil.
** Annette Hargrove is Madame de Tourvel.
** Cecile Caldwell is Cécile de Volanges.
** Ronald Clifford is Chevalier Danceny.
** Bunny Caldwell is Madame de Volanges.
** Court Reynolds is Comte de Gercourt.
** Helen Rosemond is Madame de Rosemonde.
** Blaine Tuttle is Azolan.
** Greg [=McConnell=] is Julie.
** Mai-Lee is Victoire (sort of -- she's just Kathryn's maid, not an accomplice in her schemes).
** Gretchen and Mora are both Emilie (in a deleted scene).
** Sebastian's journal represents the letters Vicomte de Valmont possessed.
%%* FauxAffablyEvil: Kathryn.
* FilleFatale: Kathryn is the poster child of this trope. While she's a brilliant ChessMaster, her body is her weapon of choice for manipulating boys -- and sometimes even girls.
* FlirtyStepsiblings: Sebastian and Kathryn really push the envelope as far as they can with this trope. There's nothing subtle about the stepbrother and stepsister's sexual attraction to each other -- viewers are clearly supposed to be shocked and disgusted, if not salaciously turned on.
* ForTheEvulz
--> '''Kathryn:''' You were very much in love with her. And you're still in love with her. But [[ItAmusedMe it amused me]] to make you ashamed of it. You gave up on the first person you ever loved because I threatened your reputation. Don't you get it? You're just a toy, Sebastian. A little toy I like to play with. And now you've completely blown it with her. I think it's the saddest thing I've ever heard.
* [[FrenchJerk French Jerks]]: Okay, technically Sebastian and Kathryn are French-''Americans''. But, they're still jerks.
* FreudianCouch: Sebastian lies on the couch in his therapist's office.
* FreudianExcuse: Kathryn states hers in one scene to Sebastian.
--> '''Kathryn:''' Eat me, Sebastian. It's okay for guys like you and Court to fuck everyone... ...but when I do it, I get dumped for innocent little twits like Cecile. God forbid I exude confidence and enjoy sex. Do you think I relish acting like Mary Sunshine twenty-four seven so I can be considered a lady? I'm the Marcia-[[PrecisionFStrike fucking]]-Brady of the Upper East Side... ...and sometimes I want to kill myself. There's your psychoanalysis, Dr. Freud. Now tell me, are you in, or are you out?
** In the prequel, a sobbing Kathryn uses the [[AbusiveParents emotional abuse she endures from her mother]] as her excuse for being so mean.
* FunctionalAddict: Supposedly, Kathryn somehow manages to balance a hard drug addiction and alcoholism with an exemplary academic resume (by blackmailing all her teachers perhaps?).
* GenreBlindness:
-->'''Annette''': It amazes me someone as charming as you can be so manipulative.
** [[BigWhat WHAT?!]] Manipulative people are charming instead of blatant {{Jerkass}}es?
* GenreSavvy: Sebastian uses the oldest trick in the book to make a girl fall in love with you in a teen movie: Act as insufferably obnoxious as possible to get her to [[BelligerentSexualTension despise you and then suddenly realize she can't resist you]].
** Averted in ''Cruel Intentions 2'' in which his gestures toward Danielle are actually kind of romantic, albeit a bit [[StalkerWithACrush creepy]], making it a KickTheDog moment when [[spoiler: she reveals she was playing him for a [[TheFool fool]] the whole time]].
* GettingCrapPastTheRadar: Sebastian isn't interested in his stepsister's offer of sex if he wins until Kathryn adds, "You can put it anywhere..."
* GirlInTheTower: Invoked metaphorically. Like an overthrown princess, Kathryn [[GreenEyedMonster sullenly watches]] from a darkened balcony of the Valmont mansion as Sebastian gives Annette a [[SealedWithAKiss goodnight kiss]] on the street down below.
* GoodIsNotSoft: Unlike other versions of the character, Annette is no DamselInDistress. Instead of allowing herself to be the victim of the story and [[DeathByDespair dying of a broken heart]], she fights back and [[spoiler: serves Kathryn her JustDesserts in the end]].
* GoodSmokingEvilSmoking: Sebastian is an "evil smoker."
* GrandeDame: Tiffany Merteuil uses her status in the community to persuade NouveauRiche {{Social Climber}}s to "throw money" at her [[{{Main/Egopolis}} self-serving charity]], as Kathryn puts it.
* HairOfGoldHeartOfGold: Beautiful young virgin Annette.
* HandsOnApproach: Cecile and her music teacher Ronald, with a Cello.
* HeelFaceTurn: Sebastian, who's every bit as slimy as his stepsister at the beginning, just couldn't continue being such a jerk after Annette genuinely won his heart. [[spoiler: According to information on the television series, Kathryn by all appearances seems to have made one too following the film, even running a rehab movement for troubled youths like she used to be. [[SubvertedTrope However...]]]]
* HeroicSacrifice: [[spoiler:After Annette is pushed onto the road by Ronald during his and Sebastian's fight, Sebastian pushes her out of the way of an oncoming car and gets hit himself. He would succumb to the accident.]]
* HighSchoolAU: of DangerousLiaisons.
* HookersAndBlow: Sebastian and Kathryn make drugs and debauchery look so glamorous.
* IceQueen: Kathryn is the archetypal cold-hearted ice princess whose opulent bedroom is a [[StealthPun cold, dark lair decorated in royal blue and silver with crystal embellishments]]. When she's not wearing [[ColorCodedForYourConvenience black, gray or other dark, muted colors, she occasionally wears icy blue]].
* IdleRich: Sebastian and Kathryn each get a weekly five-figure allowance. And no, they don't mow the lawn for it. Meanwhile, middle-class Danielle has an after-school job at a used bookstore.
* ImBack: Sebastian tries to invoke this after [[spoiler: breaking up with Annette]], but he overdoes his performance and he's clearly been crying, so it's not all that convincing.
* IncorruptiblePurePureness: Annette prides herself on being a "paradigm of chastity and virtue" so much that she published a self-righteous magazine article about the simple fact that she's managed to stay a virgin for all 17 years of her life. Apparently, this makes her a rare jewel since we all know that [[OfCourseImNotAVirgin all teenagers are sexually active]] -- at least, that's what ''Cruel Intentions'' wants us to believe. Or maybe it's the fact that she's a [[EveryoneLovesBlondes beautiful blonde]] and a virgin that makes her so [[SpecialSnowflakeSyndrome unique]]. Who even knows?
* InstantSeduction: Sebastian, apparently. In his first scene he tells a girl that she's beautiful, and the next we see him a few hours later he's already had sex with her.
* InvisibleParents: Sebastian and Kathryn's parents are only vaguely mentioned as being out of the country in the first film. Also, Annette is staying with Sebastian's aunt in the Hamptons while her parents sell their house back in Kansas.
* IronicEcho: Annette meets Kathryn at the end, just before [[spoiler:it emerges she's released the journal, thus destroying the latter's reputation]] and turns her "in times of trouble, I turn to Jesus" line on her. Kathryn doesn't realise a thing.
* KickTheSonOfABitch: The deleted scene in which Sebastian slaps Kathryn. Good God, did she deserve it. Unfortunately, the scene had to be deleted because Sebastian then went too far ''after'' the slap, almost forcing himself on Kathryn sexually.
* KidAnova: At 17, Sebastian is already "sick of sleeping with these insipid Manhattan debutantes."
* KissingCousins / {{Twincest}}: The twins in the second movie claim to be KissingCousins, but were played by RealLife twins.
* LackOfEmpathy: Kathryn tells her maid she can empathize with Khmer Rouge refugees because she ''almost'' had to fly coach one time. She also tells her stablehand over the phone how badly she feels that he or she will just have to cancel his or her daughter's birthday to groom Kathryn's horse.
%%* LadykillerInLove: Sebastian.
* LameRhymeDodge: Said by Sebastian to an elderly woman who's hard of hearing.
-->'''Sebastian''': Then I fucked your daughter.
-->'''Woman''': What?!?!?
-->'''Sebastian''': I said, would you like some water?
* LargeHam:
** Ronald. "THE BLACK MAN IS GONE! THE BLACK MAN IS GONE!"
** Cecile's mother, played by Christine Baranski.
* LaserGuidedKarma: [[spoiler: Kathryn's downfall comes about from people whom she screwed over. Her secrets are exposed by the journal of Sebastian, which was copied by Annette and distributed to the student body by Cecile.]]
* LeanAndMean: In the form of the rail-like Kathryn.
%%* LightFeminineAndDarkFeminine: Annette and Kathryn.
* LightIsNotGood: Kathryn can't seem to stop telling people how fortunate she is to be a part of the Christian faith. She speaks as if Jesus Christ is her greatest ally and even wears a rosary as a necklace in public. But despite all that she is an insufferable elitist, and manipulative, spiteful and cruel, and stashes cocaine inside a hollowed-out crucifix at the end of her rosary.
* LoveIsAWeakness: The movie's tagline is "In the game of seduction, there is only [[BlueAndOrangeMorality one rule]]: Never fall in [[ThePowerOfLove love]]." [[LonelyRichKid Kathryn and Sebastian]] (at first) both live by this [[StrawNihilist philosophy]], which she uses as the basis for her ReasonYouSuckSpeech against him.
* LoveRedeems: Sebastian, sort of. He comes clean about everything and sacrifices his life for Anette.
* MadonnaWhoreComplex: Kathryn speaks against this, talking about the DoubleStandard of boys being able to sleep around while she must pretend to be a Madonna in order to avoid being classed as a Whore. Her whole game plan is to corrupt Madonnas Annette and Cecile and turn them into Whores.
* ManipulativeBastard: Sebastian and Kathryn both excel at manipulating people to their own advantage.
* MeaningfulName:
** Sebastian's surname, Valmont, consists of the French words ''val'' (literally meaning "vale", the old-fashioned word for "valley") and ''mont'' ("mountain"). Sebastian starts out the movie "high" (cool and arrogant) but by the climax [[BreakTheHaughty has been brought low and made pathetic]].
** Cecile:
*** Kathryn and Sebastian succeed in making Cecile impure - which is ironic, because her name is the French form of "Cecilia" - the Catholic saint who is famously known as "The Incorruptible."[[note]] Her body has not decayed, despite her death occurring nearly two thousand years ago.[[/note]]
*** More irony in that St. Cecilia is the patroness of music. Cecile, by her own admission, is a DreadfulMusician.
* NouveauRiche: The Caldwells in contrast to the OldMoney Valmonts.
* NoodleIncident: Cecile's mother about Sebastian: "I can't believe they didn't expel him after what he did to the school nurse."
* NotBloodSiblings: Right before Kathryn propositions her stepbrother for anal sex, she makes it a point to clarify for the audience that her mother only married Sebastian's father fairly recently.
* OldMoney: The Valmonts in contrast to the NouveauRiche Caldwells.
* TheOmniscientCouncilOfVagueness: In ''Cruel Intentions 2'', the Manchester Tribunal convenes in the school's candle-lit attic with a a slide projector to discuss its plans to corrupt Sebastian and Cherie Claymon.
* OneDegreeOfSeparation: Sebastian and Blaine automatically draw the conclusion that Annette and Greg must know each other because they both happen to be from Kansas, a relatively large state -- and lo and behold, they're right. In fact, they grew up together.
* OperationJealousy: Kathryn tries this on Sebastian using [[spoiler:Ronald]], but it blows up in her face.
* PantyShot: Cecile Caldwell (Selma Blair) sitting on the couch with her legs open, giving a view of white panties under her khaki short skirt.
* PervertDad: Although Sebastian's dad is certainly a sleazeball, in this case, it's actually Kathryn's [[DistaffCounterpart mom]] who tries to get a little too close to her new stepson in the prequel.
* PetTheDog: Sebastian deliberately goes for this when volunteering to help Annette work at the old people home, with humorous results.
* PoliceAreUseless: The officer just seems dismayed that Sebastian rudely brushes him off after he repeatedly tries to point out that his car is in a no-parking zone.
* PopularIsDumb: Subverted as Kathryn and Sebastian are in fact pretty intelligent.
* PracticeKiss: In a LesYay example of this trope, this is proposed by ManipulativeBitch Kathryn to the innocent Cecile, who is worried about making a fool of herself when kissing her boyfriend for the first time. After the kiss Cecile is left breathless, and unconsciously leans forward for more as Kathryn pulls away.
* PreachersKid: Swap preacher for headmaster. Annette is the headmaster's daughter and daddy's little angel. Before Headmaster Hargrove takes over the position, [[SuspiciouslySimilarSubstitute Danielle Sherman]] is the same thing, only [[spoiler: she's [[BitchInSheepsClothing not what she seems]]]].
* {{Prequel}}: ''Cruel Intentions 2''....[[InNameOnly sort of]] (It was [[PoorlyDisguisedPilot actually a pilot for a TV show]] that never happened.) Ironically, Roger Kumble himself is now aiming to create a ''sequel'' TV show.
* PrisonRape: If there's one decent thing about the ''Cruel Intentions 3'' script, it's this witty line from Kathryn's cousin Cassidy, alluding to another character's earlier complaint that his promiscuous sex life has become boring: "You're off to prison, where the sex is never boring."
* PsychoExGirlfriend: [[NotGoodWithRejection Don't ever dump]] [[ClingyJealousGirl Kathryn]] [[WomanScorned if you know what's good for you]]. Furthermore, [[IfICantHaveYou don't ever date her ex-boyfriends]].
* RacistGrandma: Cecile's mother, Mrs. Caldwell, seems like a cultured philanthropist but barely conceals her decidedly ignorant views, no doubt carried over from her generation.
* RapeIsASpecialKindOfEvil: In ''Cruel Intentions 3'', [[spoiler: [[NotGoodWithRejection Patrick]]]] becomes the official villain of the movie when he crosses this line.
* ReallyGetsAround: Sebastian. Kathryn notes the hypocrisy that nobody thinks any less of him for sleeping with everyone, but she has to keep her sexual liaisons a secret.
* ReasonYouSuckSpeech: Kathryn gives one to Sebastian after she tricks him into dumping Annette.
-->'''Kathryn''': You were in love with her. And youíre still in love with her. But it amused me to make you ashamed of it. You gave up the first person you ever loved, because I threatened your reputation. Donít you get it? Youíre just a toy, Sebastian. A little toy I like to play with. And now youíve completely blown it with her. I think itís the saddest thing Iíve ever heard.Ö So I assume youíve come to make arrangements. But unfortunately, I donít fuck losers.
* RedemptionEqualsDeath: [[spoiler: Sebastian dies saving the girl he loves from a car crash and in death he owes up to his and his sisters' crimes through his journal that Annette gets published, which exposes their [[TitleDrop cruel intentions.]]]]
* RevengeByProxy: The whole reason Kathryn sets Sebastian onto Cecile is to get to Cecile's current boyfriend, who is Kathryn's ex.
* RichBitch: Kathryn, Tiffany and Cassidy Merteuil come from a line of rich bitches.
* RichBoredom: Kathryn and Sebastian seem to have nothing better to do than lounge around their palatial townhouse -- or country estate if they feel like a change of scenery -- while placing bets on how many people they can sleep with and lives they can ruin just to pass the time.
* RoyalBrat: All the servants in the Valmont house live in fear of "Miss Kathryn," but they endure her wrath simply because the Fifth Avenue mansion is a "good address" at which to be employed. As the QueenBee of her school, Kathryn treats her GirlPosse much the same way, and they're afraid to fall out of favor with her.
* ScatterbrainedSenior: Since AdultsAreUseless anyway, it should come as no surprise that the residents at the nursing home that Sebastian and Annette visit are adorably senile.
* ScrewTheRulesIHaveConnections: ''Cruel Intentions 2'' invokes this trope often to explain how the characters are able to pull off some pretty [[WillingSuspensionOfDisbelief unbelievable]] scams (e.g., Sebastian switching his high school transcript with a forgery; Kathryn getting her hands on the real one).
** In ''Cruel Intentions 3'', Cassidy's father founded an entire dorm hall just so she could have her own private suite, decked out in just about every standard college room code violation you can think of.
* ScrewTheRulesIHaveMoney: Sebastian feels entitled to park anywhere he pleases in New York City because, naturally, parking tickets are no big deal when you're a SpoiledBrat.
* SecretCircleOfSecrets: Kathryn's many extracurricular activities include running the Manchester Tribunal, a secret society ([[IfOnlyYouKnew if only Cecile knew]]) of cruel popular kids at her snobby prep school. Basically, it's a rip-off of the [[TheIlluminati Skull and Bones]] fraternity at Yale. Orders of business include such dastardly plans as [[ArsonMurderAndJaywalking ruining classmates' reputations, getting faculty members fired and scoring tickets to the Hole concert]].
* SecretDiary: Sebastian has one, as a carry-over from the original novel (which was made up of letters the characters wrote to each other). [[spoiler: It's what exposes Kathryn at the end]].
* SettingUpdate: Of ''Literature/DangerousLiaisons''. It takes it from 18th century France to 1990s New York City, changing all the characters to teenagers.
* ShowerScene: ''Cruel Intentions 2'' has a shower scene with a pair of [[{{Twincest}} twins]] [[ShowerOfLove making out]] in front of Sebastian, which, incidentally, is the [[BestKnownForTheFanservice only thing people remember]] about the film.
* SinisterShades: [[spoiler: After Ronald is fired by Mrs Caldwell, he is met outside the elevator by Sebastian and Kathryn, who are both wearing sunglasses and smirking, with the intentions of using Ronald's affiliation with Cecile to further their bet.]] Also, Sebastian is seen wearing the same shades in his first introductory scene, driving to his therapy session with Dr Greenbaum, where it is revealed he had been [[spoiler: seducing Greenbaum's daughter to humiliate her.]] At the end, Annette's final scene [[spoiler:(after outing Kathryn) is her driving out of New York City in Sebastian's car, his journal beside her, and smirking somewhat deviously...while wearing Sebastian's sunglasses.]]
* SissyVillain: Sebastian, who is symbolically emasculated not only by Kathryn[[note]] "I'll fuck your brains out" - not the other way around [[/note]], but also in a way by Cecile[[note]] he blows her, which is more often thought of as something a woman does to a man rather than the reverse [[/note]].
* SmugSnake: Kathryn spirals into this toward the end. For much of the movie, she's very competant and successful at manipulation, but she ''really'' overreaches when she turns on Sebastian, whose assistance was a big contributor to her past success.
* SocialClimber: Bunny Caldwell hopes Kathryn will take Cecile under her wing so the {{AlphaBitch}}'s popularity will rub off on her socially awkward daughter. In the prequel, [[SuspiciouslySimilarSubstitute Bunny Claymon]] has the exact same hopes for her daughter [[SuspiciouslySimilarSubstitute Cherie]].
* SomeOfMyBestFriendsAreX: Cecileís mom denies disapproving of Ronald dating Cecile because heís black, citing the fact that sheís donated money to Colin Powellís foundation. [[SarcasmMode Ronald is duly impressed]].
* SophisticatedAsHell: Sebastian and Kathryn, being afforded the best education money can buy, mix phrases such as "[[GratuitousFrench au contraire]]" with adolescent potty-mouth language.
* SparedByTheAdaptation: The ending of the stage musical parody ambiguously suggests that Sebastian faked his death to expose Kathryn.
* SpitTrailKiss: The infamous lesbian kiss between Kathryn and Cecile was like this.
* StealthPun: ''Cruel Intentions'' contains quite a few of these:
** Just like the sterling cross in which Kathryn hides her drugs, she looks like a saint on the outside, but on the inside, she's filled with pure sin.
** Sebastian sports a hunting jacket when he first meets his "prey," Annette.
** Kathryn wears a snakeskin-print dress as she [[SnakesAreSexy "slithers" seductively onto Sebastian's lap]] and [[SnakesAreSinister hatches an evil plan]].
** Cecile wears a [[{{Literature/LittleRedRidingHood}} red hoodie]] when she sneaks out to go see [[TheBigBadWolf Sebastian]].
** Kathryn's [[ColorCodedForYourConvenience blue-and-silver]] [[SupervillainLair bedroom]] is a rather obvious one (see IceQueen above).
*** On a similar note, it's interesting to note that her drug of choice sometimes goes by the street name "snow."
** Sebastian has a bowl of maraschino cherries on his nightstand after he pops Cecile's cherry.
** In the DVD commentary, the director points out that the way Sebastian suggestively points the [[DoesThisRemindYouOfAnything neck of the champagne bottle]] toward his face when he says he and Kathryn should celebrate was intentional.
** The way Sebastian strokes the [[DoesThisRemindYouOfAnything handle of his tennis racket]] when he taunts Cecile isn't so stealthy.
* StepfordSmiler: Kathryn pretends to be an upstanding Junior League-type schoolgirl, when in reality she's an oversexed, scheming coke fiend who takes out her frustrations on her fellow female classmates by persuading them to sleep around and ruin their reputations as a result.
* StrawHypocrite: [[IncorruptiblePurePureness Everything Kathryn professes to stand for]] is one big [[ConsummateLiar fabrication]].
* TearsOfRemorse: [[spoiler: Kathryn]] at the end of the film, once she [[spoiler: is exposed as the manipulative bitch she is and, upon reading about herself in Sebastian's published journal, she finally seems to grasp how messed up a person she is. Also, Sebastian wrote of her as being "my true love" despite all her faults, making her feel guilty about her indirect role in his death.]]
%%* TheFool: Realistically, Cecile seems to have more or less average intelligence for a 15-year-old girl, but she's treated as though she's mentally handicapped by her more sophisticated peers, which is continually PlayedforLaughs. More than anything, she's simply naive and lacks social graces. At the end of the film, she finally understands the other characters' true motivations and helps to take down Kathryn.
* TheGhost: Allegedly, Annette is already in a committed relationship with a loving boyfriend known as "Trevor," who's conveniently absent for the entire movie as Sebastian moves in on her. Also, Court is supposed to be Cecile's official boyfriend, yet he only makes one appearance in a flashback, and the two are never seen together.
* TheJeeves: Naturally, the Valmont house has a proper English butler to manage a full staff of diverse EthnicMenialLabor stereotypes.
* ThePreciousPreciousCar: Sebastian's 1956 Jaguar XK 140 Roadster is his most prized possession. If he loses his bet with Kathryn, he has to hand it over to her. [[spoiler:After Sebastian dies, Annette somehow ends up with the car. Although, production stills from the upcoming NBC spin-off TV series appear to show Kathryn eventually ends up with the car in San Francisco. Apparently, she hands it over to Sebastian and Annette's [[BastardBastard son]], Bash Casey, once [[RightfulKingReturns he comes out of the woodwork to claim his family name]].]]
* TheTease: Kathryn, at one point grinding on Sebastian to convince him to sleep with Cecile.
* TeensAreMonsters: Especially in the prequel, and even more especially in the unaired episodes of the canceled television series that became the prequel. Almost every student at Manchester Prep turns out to be every bit as cruel as Kathryn and Sebastian.
* ThereAreNoAdults: The few adults who do exist on rare occasions are clueless or indifferent to what the kids are up to. Either way, they are not individuals to whom the children can appeal.
* TheThreeFacesOfEve: The three girls: Annette (wise and mature) as the wife, Kathryn (cold, manipulative FemmeFatale) as the seductress and Cecile (sheltered NaiveEverygirl) as the child.
* TokenMinority: Subverted, as the minority characters are there for the sake of blatant political ''in''correctness. The one black cast member's race is a source of major contention in the story line, and the two gay characters are the butt of "fag"[[note]]Sebastian adds [[InsultFriendlyFire "no offense"]] afterward.[[/note]] and "fudge-packer" jokes.
* TookALevelInJerkass: Again, Cecile, who gets more bitchy and slutty as the film goes on, just as Kathryn had planned.
* TotallyRadical: Cecile's dialogue, particularly when she says goodbye to Ronald with "Peace out!" much to Kathyrn's disgust.
* {{Tsundere}}: Sebastian pretty much accuses Annette of being this at one point ("Hot one minute, cold the next")
* 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.
* UnholyMatrimony: Sebastian and Kathryn's parents. When she tells him that her mother suspects his "drunk, impotent" father of doing the maid he says excellent, while he calls her mother a "gold digging whore".
* UnsuspectinglySoused: Becomes something of a running gag across the series.
* VillainousBreakdown:
** Sebastian ''originally'' had one when Kathryn refuses to sleep with him even after he dumps Annette, going into a tearful, psychotic tirade and even hitting Kathryn. However, it was cut out because it lessened the feeling that Sebastian could truly be redeemed. Interestingly, Kathryn still tells Ronald that Sebastian hit her, [[WoundedGazelleGambit making it seem like a lie]] when it was originally meant to be true.
* VillainWithGoodPublicity: Kathryn is obsessed with maintaining her wholesome reputation as the student body president who attributes all her success to her unwavering piety, and she'll go to any length to destroy anyone who threatens the image that she's worked so hard to create.
* VillainProtagonist: Sebastian is the protagonist of the movie despite being a thoroughly [[TheSociopath horrible person]], only becoming sympathetic [[HeelFaceTurn toward the end]].
* VirginityFlag: [[spoiler:Annette]] suddenly wears dark clothes with a more revealing neckline in contrast to her former high-necked pastel wardrobe. Sebastian also wears a bright blue shirt to symbolize that he has [[spoiler:fallen in love with her]].
* VirginityMakesYouStupid: Subverted with Annette, played straight with Cecile. Not that Cecile is any smarter afterward.
* WeightWoe: Just to further prove how RoyallyScrewedUp Kathryn is, she suffers from bulimia and, according to Sebastian, even purges a big salad if it has croutons in it.
* WhereDaWhiteWomenAt: Ronald is instantly smitten with Cecile as well as, as it turns out, [[spoiler:Kathryn]] despite that neither really seems like his type personality-wise. Suffice it to say, Cecile's mother does not approve of her daughter liking her men like she likes her coffee.
** In a deleted scene, [[spoiler:Kathryn uses the scandalous nature of her relationship with Ronald to her advantage by manipulating him into believing that Sebastian is a violent racist]].
* WickedCultured: Kathryn speaks Vietnamese, French and has sashimi as a midday snack. Sebastian rides, is an expert marksman and quite well read. He also drives a vintage Jaguar, which Kathryn covets.
* WickedStepmother: Kathryn's mother tells Sebastian in no uncertain terms that if he doesn't keep an eye on his [[YourCheatingHeart philandering father]], the two of them will both be [[GettingTheBoot kicked "out on the street."]]
* WomanScorned: The story of [[ClingyJealousGirl Kathryn]]'s life. Halfway through the film, she delivers a MotiveRant about how she's [[NotGoodWithRejection sick of being dumped]] by guys like Court, Sebastian and Ronald for "innocent little twits" like Cecile and Annette. (Annette isn't really a twit, but Kathryn would consider her one just for being a NiceGuy.)
* VerbalBackpedaling: Mrs. Caldwell does this after a politically incorrect outburst.
-->'''Kathryn''': She's so young, and he's so --
-->'''Mrs. Caldwell''': Black! Brown sugar. No sugar.
%%* {{Yandere}}: One way of looking at Kathryn. See the ForTheEvulz entry for the other interpretation.
* "YouDoNOTWantToKnow," Cecile says about being taken advantage of.
* YourCheatingHeart: This is essentially the entire plot of the story. [[spoiler:Annette cheats on Trevor both physically and emotionally with Sebastian. Sebastian [[GreenEyedMonster arguably cheats on Kathryn emotionally]] with Annette. He also cheats on Annette physically with Cecile. Cecile cheats on Court at least emotionally, [[DidTheyOrDidntThey if not physically]], with Ronald. She also cheats on both of them physically with Sebastian. Ronald cheats on Cecile physically with Kathryn. Kathryn hooks up with Ronald to make Sebastian jealous. It's implied that Court cheated on Kathryn with Cecile at least emotionally. And everybody lives -- or dies -- unhappily ever after]].
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