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

''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:

* 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.
* AgeLift: Kathryn and Sebastian's counterparts in the novel were in their 40s but are now around seventeen.
* 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 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.
* 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.
* 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.
* 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.
%%* BitchInSheepsClothing: Kathryn.
* 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.
* 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: Blaine.
* CantHoldHisLiquor: Cecile gets pretty tipsy off one Long Island Iced Tea.
* 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.]]
* 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.
* 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.]]
%%* CorruptTheCutie: Cecile.
* 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.
%%* TheDitz: Cecile.
* 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.]]
* EvilGloating: Kathryn sure loves doing this. Half her lines consist of it.
* 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 Rosemont is Madame de Rosemonde
** Sebastian's journal represents the letters Vicomte de Valmont possessed
%%* FauxAffablyEvil: Kathryn.
%%* FilleFatale: Kathryn is the poster child of this trope.
%%* FlirtyStepsiblings
* 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: Inside the Valmont residence.
* 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?
* GettingCrapPastTheRadar: Sebastian isn't interested in his stepsister's offer of sex if he wins until Kathryn adds, "You can put it anywhere..."
* GoodSmokingEvilSmoking: Sebastian is an "evil smoker".
* 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.]]
* 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.
* 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.
* 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: Sebastian.
* KissingCousins / {{Twincest}}: The twins in the second movie claim to be KissingCousins, but were played by RealLife twins.
%%* LackofEmpathy: Kathryn, so very much.
%%* 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:
** 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.
%%* LoveRedeems: Sebastian, sort of.
* LoveMakesYouEvil: The last shot of the movie, [[spoiler: (Annette driving Sebastian's car, wearing Sebastian's sunglasses, and smirking [[BookEnds like Sebastian did at the start of the movie]]) indicates that loving Sebastian may not have been all too good for Annette...]] The [[WhatCouldHaveBeen original ending]] was far less ambiguous; in it, [[spoiler: Annette DOES become evil and, instead of publishing Sebastian's journal and expose Kathryn, uses the possibility of doing that to blackmail Kathryn into becoming her minion, who she plans on using to completely fuck around with the social order of her father's school.]]
* 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.
%%* ManipulativeBitch: Kathryn, IN SPADES.
* NoodleIncident: Cecile's mother about Sebastian: "I can't believe they didn't expel him after what he did to the school nurse."
%%* NotBloodSiblings: Sebastian Valmont and Kathryn Merteul.
* PantyShot: Cecile Caldwell (Selma Blair) sitting on the couch with her legs open, giving a view of white panties under her khaki short skirt.
* PetTheDog: Sebastian deliberately goes for this when volunteering to help Annette work at the old people home, with humorous results.
* 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.
* {{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.
* 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.
* RichBoredom: Supposedly, Kathryn somehow manages to balance a hard drug addiction and alcoholism and an exemplary academic resume (by blackmailing all her teachers perhaps?). Yet as far as we can tell, she 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.
* 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.]]
* 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.
* 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]].
* SpitTrailKiss: The infamous lesbian kiss between Kathryn and Cecile was like this.
* StepfordSmiler: Katherine 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.
* 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.]]
* 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.
* 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: Cecile's 'unsuitable' lover, Ronald. Kathryn was expecting Cecile's mother to be shocked at the idea of her daughter dating the "hired help". She's surprised when the mother is instead horrified because Ronald's ''black''.
* 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")
* 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:
%%** Kathryn at the end.
** 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, until the very end.
%%* VillainProtagonist
* 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.
%%* WhereDaWhiteWomenAt: Ronald with Cecile and Kathryn.
* 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.
%%* WomanScorned
%%* {{Yandere}}: One way of looking at Kathryn. See the ForTheEvulz entry for the other interpretation.
* YourCheatingHeart: Cecile is in a relationship with Court Reynolds, who only shows up in a flashback, but falls for Ronald and ends up with him as well.