Characters / Cruel Intentions

Sebastian Valmont

Sebastian Valmont

Played by Ryan Phillippe & Robin Dunne (Cruel Intention 2)

"I'm sick of sleeping with these insipid Manhattan debutantes. Nothing shocks them anymore."

• Adaptational Heroism: While still an Anti-Hero, Sebastian is presented far more sympathetically than his counterpart in the original novel and its adaptations.
• All Girls Want Bad Boys: Sebastian's main charm seems to be that he is a "bad boy," which ultimately works on Annette.
• Am I Just a Toy to You?: Sebastian tells 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.
• Anguished Declaration of Love: Sebastian delivers one to Annette in his letters and while he is dying.
• Batman Cold Open: Sebastian's session with the psychologist to deal with his "sexual addiction." This also serves as his Establishing Character Moment, 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.
• Betty and Veronica: Sebastian must choose between his affections for the sweet, blonde Annette and the cruel, dark-haired Kathryn.
  • In the prequel, Kathryn is an icy blonde (but still the Veronica), while his Betty is a dark-haired bookworm Danielle who has a job in a Bookstore and only attends Manchester Prep due to her father’s job as Headmaster. Of course, it’s later revealed that Danielle is just as mean as Kathryn.
• The Bet: The whole plot revolves around a bet two stepsiblings 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.
• Brother–Sister Incest: In the film, Sebastian and Kathryn are Flirty Stepsiblings. Kathryn offers to let him have sex with her if he wins The Bet, since (according to her), she's the one person he can't have. He wins, but when he comes to collect, she just laughs in his face, as by then he's genuinely in love with someone else. It's implied it's because she's jealous, though. He tries to rape her in a deleted scene, but it was cut due to the director thinking (correctly) that it would cause the audience to lose sympathy for him.
• Black Comedy: If Sebastian's angst and the tragic climax and [Melodrama denouement]] were edited out, then the whole film could pass as one. The opening scene alone is a comedic masterpiece.
• Black Comedy Rape: Sebastian essentially date-rapes Cecile by first getting her Unsuspectingly Soused and then using coercion to make her relent to him performing sex acts on her. And it's Played for Laughs the whole time. For an added dose of irony, the cringey scene is set to dulcet tones about love.
• The Cake Is a Lie: When Sebastian comes to collect from Kathryn, she just laughs in his face and gives him a "Reason You Suck" Speech. Unusually for this trope, there is no indication that it was a lie from the start, and it seems like Kathryn intended to keep her end of the deal until she realized Sebastian had truly fallen for Annette and got jealous.
• Camera Fiend: Sebastian seduces the psychiatrist's daughter by taking pictures of her legs. Later, he's seen photographing a blithely ignorant Cecile.
• Chekhov's Gun: 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.
• Cool Car: Sebastian's Jaguar, which Kathryn has her eye on. In the end, Annette drives it off into the sunset after exposing Kathryn at Sebastian's funeral.
• Corrupt the Cutie: Sebastian's summer project is to conquer the headmaster's daughter Annette's Incorruptible Pure Pureness.
• Dies Differently in Adaptation: Taking into consideration the source material, Sebastian does not die in a Duel to the Death with the angry lover of the woman he seduced. While he still gets in a fight with the Danceny stand-in, it's an oncoming car that hits Sebastian and does him in.
• Diving Save: Sebastian does this to save Annette from an oncoming taxi.
• Dying Declaration of Love: Before dying, Sebastian confesses his love for her and Annette tells him she loves him, too..
• Double Entendre: Sebastian isn't interested in his stepsister's offer of sex if he wins until Kathryn adds, "You can put it anywhere..."
  • When Sebastian greets Cecile and notices she's wearing a koala t-shirt: "How are things down-under Australia? Blossoming, I hope?
• Expy: Sebastian Valmont is Vicomte de Valmont.
• Establishing Character Moment: Sebastian is introduced as cultivated and sensitive person Sebastian talking about his progress in maturing to his psychiatrist.
• Explain, Explain... Oh, Crap!: When Sebastian's therapist's daughter Marci calls in tears. Describing how the boy she loved was so charming. All he did say was how "she had killer legs and how he wanted to photograph them". Cue the Oh, Crap! look on the infuriated mother/therapist's face when she realizes she is describing her patient Sebastian who just left.
• Flirty Stepsiblings: 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.
• Foreshadowing: The opening shot of the film is an extended scene of a graveyard, then the camera turns to follow Sebastian driving past it. This appears to foreshadow his eventual death at the end of the film.
• Good Smoking, Evil Smoking: Sebastian is an "evil smoker."
• Heel–Face Turn: 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.
• Heroic Sacrifice: 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, dying shortly after.
• It Doesn't Mean Anything: Sebastian lies to Annette, claiming he just wanted to see what she was like in bed, and that he has no real feelings for her.
• Interrupted Intimacy: Sebastian busts in on the popular, wealthy and muscular football player at his and Kathryn’s school Greg having sex with Sebastian’s gay friend Blaine. Sebastian takes photos of Greg and Blaine in their underwear and blackmails a nervous Greg to put a good word in about him to Annette.
• Instant Seduction: 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.
• Invisible Parents: 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.
• KidAnova: At 17, Sebastian is already "sick of sleeping with these insipid Manhattan debutantes."
• Ladykiller in Love: Sebastian start falls deeply love with Annette.
• Lame Rhyme Dodge: 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?
• Love Redeems: Sebastian, sort of. He comes clean about everything and sacrifices his life for Annette.
• Meaningful Name:
  • 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 has been brought low and made pathetic.
• Manipulative Bastard: Sebastian and Kathryn both excel at manipulating people to their own advantage.
• My God, What Have I Done?: Sebastian, after dumping Annette for Kathryn and realizing Kathryn was just using him.
• One Degree of Separation: 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.
• Pet the Dog: Sebastian deliberately goes for this when volunteering to help Annette work at the old people home, with humorous results.
• Posthumous Villain Victory: Sebastian dies but he succeeds in exposing Kathryn's dirty secrets posthumously when her journals are copied into many and then passed around to read at his funeral so her reputation is tarnished.
• The Precious, Precious Car: 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. After Sebastian dies, Annette ends up with the car.
• Race for Your Love: Sebastian tracks Annette down at the train station where he professes his love for her and they consummate their relationship soon after.
• "Reason You Suck" Speech: Sebastian delivers one to Annette about "waiting for love" as he attempts to manipulate her into sleeping with her only to back out and run away.
  Sebastian: You spend all your time preaching about waiting for love. Well here it is. Right in front of you, and you're going to turn your back on it. So I guess we're just fucked. I'll move on. But you are going to have to live the rest of your life knowing that you've turned your back on love. And that makes you a hypocrite. Have a nice life.
• Redemption Equals Death: 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 cruel intentions.
• Rich Boredom: Sebastian and Kathryn 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.
• Screw the Rules, I Have Money!: Sebastian feels entitled to park anywhere he pleases in New York City because, naturally, parking tickets are no big deal when you're a Spoiled Brat.
• Secret Diary: Sebastian has one, as a carry-over from the original novel (which was made up of letters the characters wrote to each other). It's what exposes Kathryn at the end.
• Sissy Villain: Sebastian, played by pretty boy Ryan Phillippe, gets symbolically emasculated by Kathryn"I'll fuck your brains out" - not the other way around.
• Snark-to-Snark Combat: Almost every conversation between Sebastian and Kathryn. From the first time we see them talk:
  Sebastian: How is your gold-digging whore of a mother enjoying Bali?
  Kathryn: She suspects your impotent, alcoholic father is diddling the maid.
• The Sociopath: Sebastian have elements of this: superficial charm, sexual promiscuity, lack of meaningful relationships, manipulation of others. Ultimately subverted, as he is revealed to have genuine feelings and falls in love with Annette.
• Unholy Matrimony: Sebastian and Kathryn's parents. When she tells him that her mother suspects his "impotent alcoholic" father of diddling the maid he simply says “excellent”, while he calls her mother a "gold digging whore".
• Villain Protagonist: Sebastian is the protagonist of the movie despite being a thoroughly horrible person, only becoming sympathetic toward the end.
• Wham Shot: The journal Sebastian gifts Annette with, detailing the truth about him and Kathryn.

Kathryn Merteuil

Kathryn Merteuil

Played by Sarah Michelle Gellar & Amy Adams (Cruel Intentions 2)

"Everybody loves me. And I intend to keep it that way."

• Abusive Parents: Despite Kathryn's impressive academic record and leadership roles as well as her talents at piano, foreign languages and English vocabulary, her perfectionist mother constantly reminds her daughter what a disappointment she is for failing to live up to her impossibly high expectations.
• A Glass of Chianti: Kathryn holds a glass of champagne while Evil Gloating.
• Alcoholic Parent: Kathryn refers to Sebastian's "impotent, alcoholic father" in the first film.
• Almost Kiss: Several between Kathryn and her stepbrother Sebastian.
• Alpha Bitch: 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 she isn't really happy with her life. Honestly, her desire to humiliate other girls is more out of envy than pure sadism.
• Ambiguously Bi: Kathryn is clearly interested in men, including but not limited to her stepbrother, but she also describes Cecile in a rather sensual manner and gladly made out with her in public. She claimed it was to help Cecile practice, but it's easy to interpret the move as her enjoying it for herself.
• As You Know: 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:
• Bad Girl Song: In the musical, Kathryn gets "Genie in a Bottle" when she seduces Sebastian. Cecile's rendition of "I'll Make Love to You" is an utterly hilarious version.
• Be a Whore to Get Your Man: Kathryn literally tells Cecile to do this.
• The Bet: The whole plot revolves around a bet two stepsiblings 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.
• Bait-and-Switch Lesbians: At first it seems as though Kathryn is going to seduce Cecile to get back at Court. Only it turns out to be nothing more but (as Cecile believes) friendship and a Practice Kiss. And Kathryn is just using practice with Cecile as an excuse to french kiss her.
• Bitch in Sheep's Clothing: Kathryn's M.O. is to befriend her naïve classmates and take them under her wing so she can subtly be a bad influence on them.
• Bittersweet Ending: 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") Cry For The Devil 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.
• Brainy Brunette: Kathryn has Dark Brown hair. She also speaks three languages (English, French, and Vietnamese), is a talented pianist, has an excellent vocabulary, and excessive academic achievements.
• Brother–Sister Incest: In the film, Kathryn and Sebastian are Flirty Stepsiblings. Kathryn offers to let him have sex with her if he wins The Bet, since (according to her), she's the one person he can't have. He wins, but when he comes to collect, she just laughs in his face, as by then he's genuinely in love with someone else. It's implied it's because she's jealous, though. He tries to rape her in a deleted scene, but it was cut due to the director thinking (correctly) that it would cause the audience to lose sympathy for him]].
• Brother–Sister Team: The manipulative Kathryn Merteuil and Sebastian Valmont are step-siblings - and yes, that particular loophole is milked for all it's worth.
• Butt-Monkey:
  • Kathryn pretends to be Cecile friend, but tells her racist mother about her secret romance with a black guy. Then Kathryn manipulates her into sleeping with Sebastian while sleeping with the black guy herself.
• Corrupt the Cutie: Kathryn makes it her mission to turn her ex's new girlfriend Cecile into the "premier tramp of the New York area" and enlists Sebastian's help.
• Depraved Bisexual: 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.
• Disappeared Dad: It's unknown who or where Kathryn's biological father is.
• Disappointed in You: A non-verbal example. When Kathryn's drugs and acts of crime are discovered at the end, an older man discovers himself that her cross is actually filled with cocaine and lowers his gaze in disapproval at her.
• Dramatic Shattering: Kathryn flies into a rage when Sebastian doesn't want to fuck her anymore and throws a wine glass at him, shattering against her bedroom door as he shuts it behind him on the way out.
• Drugs Are Bad: Kathryn abuses cocaine, alcohol and eating disorders in order to fuel her evil plans for revenge. Comes back to bite her in the end when an older gentleman (either the school headmaster or her stepfather) grabs her crucifix, spills the cocaine out of it and shakes his head at her in shame.
• Establishing Character Moment: Kathryn is introduced as cultivated and sensitive person, Kathryn providing guidance and mentoring of the sheltered Cecile — and then immediately reveal herself to be game-playing frauds.
• Evil Gloating: Kathryn sure loves doing this. Half her lines consist of it.
• Evil Tastes Good: Kathryn basically says this in one scene.
• Expy: Kathryn Merteuil is Marquise de Merteuil.
• Faux Affably Evil: Kathryn. She'll act sweet to, for example, Cecile, but roll her eyes and mouth "Fucking idiot" when she turns around.
• Fille Fatale: Kathryn is the poster child of this trope. While she's a brilliant Chess Master, her body is her weapon of choice for manipulating boys — and sometimes even girls.
• Flirty Stepsiblings: Kathryn and Sebastian 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.
• For the Evulz: The entire reason she messes with Seasbtian.
  Kathryn: You were very much in love with her. And you're still in love with her. But 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.
• Forbidden Fruit: Invoked when she makes the bet with Sebastian and offers to let him sleep with her if he wins.
  Kathryn: Because I'm the only person you can't have, and it kills you.
• Foreshadowing: Kathryn deliberately getting Sebastian all horny and then, when he says he hasn't won the bet yet, she says "Down, boy" and walks off. It becomes much harsher when he finally wins the bet and comes to collect and Kathryn refuses to sleep with him because he's in love with Annette and she was just messing with him.
• Functional Addict: Supposedly, Kathryn somehow manages to balance a hard drug addiction and alcoholism with an exemplary academic resume (by blackmailing all her teachers perhaps?)
• Girl in the Tower: Invoked metaphorically. Like an overthrown princess, Kathryn sullenly watches from a darkened balcony of the Valmont mansion as Sebastian gives Annette a goodnight kiss on the street down below.
• Ice Queen: Kathryn is the archetypal cold-hearted ice princess whose opulent bedroom is a cold, dark lair decorated in royal blue and silver with crystal embellishments. When she's not wearing black, gray or other dark, muted colors, she occasionally wears icy blue.
• I'm Standing Right Here: When Kathryn is secretly prying information out of Cecile about her new lover Court (who was Kathryn's ex-lover), Cecile goes on talking about Court dumping a "bulimic headcase" over the 4th of July - unaware that she just described Kathryn herself.
• Invisible Parents: Kathryn and Sebastian's parents are only vaguely mentioned as being out of the country in the first film.
• Lack of Empathy: 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.
• Laser-Guided Karma: 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.
• Lean and Mean: Kathryn is rail-thin and a massive bitch.
• Light Is Not Good: 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.
• Madonna-Whore Complex: Kathryn speaks against this, talking about the Double Standard 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.
• Manipulative Bitch: Kathryn is excellent at manipulating people to her advantage, and often their downfall.
• Male Gaze: Kathryn's description of Cecile when making the bet with Sebastian: "She's quite cute, you know? Young, supple breasts. A tight, firm ass. Unchartered pooty".
• Mirror Scare: Kathryn is using the sink and is shocked to see Annette looking back at her in the girl's restroom mirror.
• More Experienced Chases the Innocent: Kathryn invokes the trope as the premise of The Bet she makes with her equally morally and sexually bankrupt step-brother Sebastian: if he can somehow sleep with Annette, the exceedingly virtuous headmaster's daughter, she'll sleep with him. Sebastian is a verifiable Casanova, as part of his introduction in the film is him flirting with a girl one scene and bedding her the next.
• Motive Rant: 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 the fact that I have to act like Mary Sunshine 24/7 so I can be considered a lady? I’m the Marcia fucking Brady of the Upper East Side, and sometimes I want to kill myself. So there’s your psychoanalysis, Dr. Freud. Now tell me, are you in, or are you out?
• Not Blood Siblings: 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.
• Not Good with Rejection: Kathryn is not happy when Sebastian turns her down for sex and is more than willing to ruin both his relationship with Annette and both their reputations unless he dumps her for her.
• "Not If They Enjoyed It" Rationalization: Kathryn thinks this when Cecile admits Sebastian got her drunk and performed oral sex on her and she liked it even though she didn't want to and Kathryn encourages her to sleep with more people.
• Oh, Crap!: Kathryn, when she goes outside and sees that everyone is reading Sebastian's journal exposing the secrets about her.
• Operation: Jealousy: Kathryn tries this on Sebastian using Ronald, but it blows up in her face.
• Practice Kiss: In a example of this trope, this is proposed by Manipulative Bitch 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.
• Psycho Ex-Girlfriend: Don't ever dump Kathryn if you know what's good for you. Furthermore,don't ever date her ex-boyfriends like Court.
• Really Gets Around: Kathryn notes to Sebastian the hypocrisy that nobody thinks any less of him for sleeping with everyone, but she has to keep her sexual liaisons a secret.
• "Reason You Suck" Speech:
  • Kathryn gives one to Sebastian after she tricks him into dumping Annette.
  Kathryn: Silly rabbit! My triumph isn't over her. It's over you. You were very much in love with her. And you’re 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. 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.… So I assume you’ve come to make arrangements. But unfortunately, I don’t fuck losers.
• Reprise Medley: Towards the end of Act Two, Kathryn gets "Kathryn's Turn Medley," which has her singing reprises of "I'm the Only One," "Genie in a Bottle," "Kiss Me," "Lovefool," and "Only Happy When It Rains," along with bits of "Bitch." (And "Losing My Religion," for Sebastian's part.)
• Revenge by Proxy: The whole reason Kathryn sets Sebastian onto Cecile is to get to Cecile's current boyfriend, who is Kathryn's ex.
• Rich Bitch: Kathryn Merteuil comes from a line of rich bitches.
• Rich Boredom: 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.
• Royal Brat: 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 Queen Bee of her school, Kathryn treats her Girl Posse much the same way, and they're afraid to fall out of favor with her.
• Shout-Out:
  • Kathryn's reference to "parental units" is from the classic 1970s Coneheads sketches on Saturday Night Live (1975).
  • When Kathryn exits the church at the end of the film, a plaque to the left of the doorway says "Rosemond Chapel." "Rosemonde" is the last name of Valmont's aunt in Les Liaisons Dangereuses.
  • After her public humiliation, Kathryn Merteuil's cross gets pulled open and her cocaine falls out, referencing the scene in Dangerous Liaisons (1988) in which the similarly disgraced Marquise de Merteuil (Glenn Close) sweeps a cloud of white powder off her dressing table.
• Smug Snake: Kathryn spirals into this toward the end. For much of the movie, she's very competent and successful at manipulation, but she really overreaches when she turns on Sebastian, whose assistance was a big contributor to her past success.
• Snark-to-Snark Combat: Almost every conversation between Kathryn and Sebastian from the first time we see them talk:
  Sebastian: How is your gold-digging whore of a mother enjoying Bali?
  Kathryn: She suspects your impotent, alcoholic father is diddling the maid.
• The Sociopath: Kathryn has elements of this: superficial charm, sexual promiscuity, lack of meaningful relationships, manipulation of others.
• Something Else Also Rises: As Kathryn grinds onto Sebastian's lap.
  Kathryn: Seems like things are looking up for you.
  Sebastian: It appears so.
• Spit-Trail Kiss: The infamous strand of saliva in the lesbian kiss between Kathryn and Cecile was like this.
• Stepford Smiler: 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.
• Straw Feminist: Kathryn whines to an eye-rolling Sebastian about how the Double Standard between boys and girls causes her to feel suicidal (literally or hyperbolically?). At least her more mature counterpart, the Marquise de Merteuil, fancies herself as a self-empowered 18th-century woman, albeit still a Straw Feminist, as she gloats to the Vicomte de Valmont about how cunningly she's learned to utilize her feminine wiles to outsmart men.
• Straw Hypocrite: Everything Kathryn professes to stand for is one big fabrication.
• The Tease: Kathryn, at one point grinding on Sebastian to convince him to sleep with Cecile.
• Took a Level in Kindness: When Kathryn and Annette meet again in the pilot Kathryn is far more civil and reasonable. She's also been sober for 15 years.
• Unholy Matrimony: Kathryn and Sebastian's parents. When she tells him that her mother suspects his "impotent alcoholic" father of diddling the maid he simply says “excellent”, while he calls her mother a "gold digging whore".
• Villain with Good Publicity: 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.
• Villainous Breakdown: In the musical, Kathryn utterly breaks down briefly before Sebastian dies, culminating in the ending of "Kathryn's Turn Medley."
  Fool me, fool me, love me, love me! Leave me...
• Wham Line: Kathryn to Sebastian after he wins the bet: "Silly rabbit! My triumph isn't over her. It's over you.". Also the start of her "The Reason You Suck" Speech to him.
• Weight Woe: Just to further prove how Royally Screwed Up Kathryn is, she suffers from bulimia and, according to Sebastian, even purges a big salad if it has croutons in it.
• Where da White Women At?: In a deleted scene, Kathryn uses the scandalous nature of her relationship with Ronald to her advantage by manipulating him into believing that Sebastian is a violent racist.
• Wicked Cultured: 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.
• Woman Scorned: The story of Kathryn's life. Halfway through the film, she delivers a Motive Rant about how she's 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 Nice Guy.
• Yandere: One way of looking at Kathryn. Kathryn offers herself to Sebastian after he wins the 'bet', but he rejects her, because he now only wants Annette, which leaves Kathryn enraged and jealous. After he breaks up with Annette for her, she turns him down and throws it in his face. Then when he still chooses Annette, she spreads lies to Ronald about Sebastian hitting her to get back at him for rejecting her for Annette. Things only get worst from there. See the For the Evulz entry for the other interpretation.

Annette Hargrove

Annette Hargrove

Played by Reese Witherspoon

"It's not all about winning, Sebastian."

• Adaptational Badass: Unlike other versions of the character, Annette is no Damsel in Distress. Instead of allowing herself to be the victim of the story and dying of a broken heart, she fights back and serves Kathryn her Just Desserts in the end.
• Babies Ever After: In the spin-off television series that never picked up, it's revealed Annette had a son named Bash after her time spent with Sebastian, and he is gifted with his late father's 1956 Jaguar XK 140 Roadster from Kathryn.
• Betty and Veronica: The sweet, blonde Betty to Kathryn's mean, cruel, dark-haired Veronica.
• Book Ends: The opening scene is the same as the last scene, except with Annette replacing Sebastian. In the original ending, this made much more sense given the state of Annette's character alignment.
• Cassandra Truth: Annette is told by Bunny Caldwell about Sebastian's true intentions.
• Dont Touch Me: Annette screams this as Sebastian breaks up with her and tries to hug her goodbye.
• Expy: Annette Hargrove is Madame de Tourvel.
• Genre Blindness:
  Annette: It amazes me someone as charming as you can be so manipulative.
• Get Out!: Annette screams this when Sebastian breaks up with her.
• The Ghost: 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.
• House Squatting: Annette is staying with Sebastian's aunt in the Hamptons while her parents sell their house back in Kansas.
• It Meant Something to Me: Annette is hurt when Sebastian dumps her, claiming to have been using her for a sexual conquest as she has fallen in love with him.
• Ironic Echo: Annette meets Kathryn at the end, just before 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 realize a thing.
• Incorruptible Pure Pureness: 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 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 beautiful blonde and a virgin that makes her so unique. Who even knows?
• Mistaken for Gay: Annette, when she rebuffers Sebastian's advances.
  Sebastian: Are you a lesbian? Sorry, I just kind of picked up on that lesbian vibe.
• Preacher's Kid: Swap preacher for headmaster. Annette is the headmaster's daughter and Daddy's little angel.
• Skinny Dipping: Annette catches a naked Sebastian going for a swim in the pools sans clothing (shot with Shoulders-Up Nudity). He's not bothered by her seeing him naked and teases her by asking her to turn when she keeps staring.
• Spared by the Adaptation: In Dangerous Liaisons, the character that Annette is based on, Madame de Tourvel, suffers grief over Valmont's death and dies from fever. In this modern retelling, Annette as the Madame de Tourvel stand-in survives, gets her revenge, and gets to drive off into the sunset. And as revealed in a spinoff television series that never got picked up, Annette even had Sebastian's son and lived on for many years after the events of Cruel Intentions.
• Virginity Flag: 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 fallen in love with her.
• What Is This Thing You Call "Love"?: Annette finally relents to sleep with him. But Sebastian, confused about his own feelings, refuses her the first time and storms off.

Cecile Caldwell

Cecile Caldwell

Player by Selma Blair

"He kept talking about this Bulimic headcase he dumped over Fourth of July . . ."

• Beta Bitch: Spends the summer thinking she's Kathryn’s best friend and avoiding the bitch part (so she thinks), but Kathryn secretly dislikes her and is plotting against Cecile in the hopes of ruining her reputation.
• Butt-Monkey: She becomes the butt of all of Kathryn's vicious, mean pranks after she unknowingly stole Kathryn’s boyfriend.
• Spoiled Sweet: She doesn't mean any harm and is merely sheltered and naive. Then again, she does make some mean comments about eating disorders among other things.