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Film / Cruel Intentions

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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, and starring Ryan Phillippe, Sarah Michelle Gellar and Reese Witherspoon. The movie is a comedic and dramatic appropriation of the 18th-century French epistolary novel Les Liaisons Dangereuses by Laclos, but unlike other modern film versions of the novel (Dangerous Liaisons) 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 was in the works for NBC, with Gellar returning to the role of Kathryn, but the network ultimately passed on the series.


In 2018, the film was adapted into a Jukebox Musical of 90s hits, which premiered Off-Broadway. The cast album is available for streaming on Spotify and YouTube.

Tropes associated with this work:

  • 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.
  • Adaptational Heroism: While still an Anti-Hero, Sebastian is presented far more sympathetically than his counterpart in the original novel and its adaptations.
  • Adults Are Useless: 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.
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  • Age-Inappropriate Dress: 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 Truth in Television. And let's not even get started on Kathryn's lingerie as daywear.
  • 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, 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.
  • All Girls Like Ponies: The second movie uses a racy version of this trope where proper horse-riding technique is used as a metaphor for sex.
  • All Girls Want Bad Boys: Sebastian's main charm seems to be that he is "bad boy," which ultimately works on Annette.
  • 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.
  • Am I Just a Toy to You?: Inverted. 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.
  • And Now For Something Completely Different: 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, though ironically it preceded most of the films it's being compared to here.
  • Archnemesis Dad: Edward Valmont and his son Sebastian have a strained relationship even though they're exactly the same.
  • Armoured Closet Gay: 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.
  • 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:
    Sebastian: Nice to see you again, Mrs. Caldwell!
    Mrs. Caldwell: You remember my daughter, Cecile.
  • 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.
  • 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.
  • 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.
  • Betty and Veronica: 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 Danielle is a warm brunette, and then subverted in the plot twist at the end when Danielle reveals that she's really just like Kathryn.
  • Bitch in Sheep's Clothing: Kathryn's M.O. is to befriend her naive 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") 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.
  • Black Comedy: If Sebastian's angst and the tragic climax and denouement were edited out, then the whole film could pass as one. The opening scene alone is a comedic masterpiece.
  • Black Comedy Rape:
  • Boarding School: Technically, Manchester Prep is a day school, but it comes with the same tropes of spoiled students picking on Scholarship Students and engaging in Situational Sexuality — except for the one perfect and kind student, of course.
  • 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.
  • 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 (probably correctly) that it would cause the audience to lose sympathy for him.
    • In Cruel Intentions 2, a pair of girls (who claim to be Kissing Cousins, but are played by real-life twins}} share a kiss in the shower while the male lead watches.
  • 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:
    • Cecile in the first movie. Kathryn pretends to be her 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.
  • 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 seducers the psychiatrists daughter by taking pictures of her legs. Later, he's seen photographing a blithely ignorant Cecile.
  • Camp Gay: You can tell Blaine is a Depraved Homosexual 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.
  • Casual Car Giveaway: Either this trope or Hero Stole My Bike is the only plausible explanation for that bizarre closing shot of Annette driving off into the desert behind the wheel of Sebastian's prized vintage Jag.
  • Casting Gag: Swoosie Kurtz appears in a modern day adaption of Les Liaison dangereuese after appearing in its seminal film adaptation a decade earlier.
  • Catholic School Girls Rule: Though their uniforms are more drab and conservative than is popularly portrayed.
  • 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.
  • Chinese Laborer: 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.
  • The Cobbler's Children Have No Shoes: 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.
  • Cold Ham: One of the pleasures of watching this film has to be watching and listening to Gellar 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 cynical California cheerleader voice she made famous.
  • Color-Coded for Your Convenience: Sebastian and Kathryn wear black and other dark colors, while Annette prefers white and pastels. Cecile initially wears white and other light colors, but shifts to wearing red as Kathryn and Sebastian begin to corrupt her.
    • In the scene where Sebastian seduces Cecile, he's wearing dark green ("go") while she's wearing bright red ("stop").
  • Consummate Liar: Kathryn, Sebastian. Annette's best friend, Greg, qualifies as well.
  • 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.
  • Cool Old Lady: 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 (wink) and pawns her charity duties off on her nephew and his girlfriend so she can go to the theater instead.
  • 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. Meanwhile, Sebastian's summer project is to conquer the headmaster's daughter Annette's Incorruptible Pure Pureness.
  • Covered in Mud: In the second film, Sebastian pushes Kathryn in a pool of mud as a declaration of war.
  • Darker and Edgier: 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 brooding, nihilistic and emotionally disturbed than their 18th-century counterparts. Add the fact that all the characters are minors, and you've got an especially disturbing tale of sexual predation and death.
    • Also Darker and Edgier as far as teen flicks go. When Cruel Intentions came out in theaters, the film's ostensible target audience couldn't even get in to see it without a parent or guardian.
  • 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.
  • Depraved Homosexual: 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.
  • Disappeared Dad: It's unknown who or where Kathryn's biological father is.
  • Divergent Character Evolution: 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.
  • Diving Save: Sebastian does this to save Annette from an oncoming taxi.
  • The Dog Bites Back: Cecile is the one that photocopied the journals. And to further add salt to the wound, she personally hands one to Kathryn.
  • 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.
  • Establishing Character Moment: Both Sebastian and Kathryn are introduced as cultured and sensitive people — Sebastian talking about his progress in maturing to his psychiatrist, Kathryn providing guidance and mentoring of the sheltered Cecile — and then immediately reveal themselves to be game-playing frauds.
  • Ethnic Menial Labor: Margarita found this trope while she was cleaning. The series loves using this trope for comedic effect: The Caldwells have a Hispanic maid who says her one line, "¡Ay, caramba!" right on cue, while the Valmonts have two different Asian maids who give pedicures, an English butler, a creepy German chef, an Arab driver who wears a turban and two Swedish masseuses. There's also a Japanese sushi chef at school. Of course, all their personalities are stereotypical and over-the-top.
  • Evil Gloating: Kathryn sure loves doing this. Half her lines consist of it.
  • Evil Matriarch: Tiffany Merteuil shows her "love" for her family by being controlling and manipulative.
  • Evil Tastes Good: 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.
  • Fanservice: Selma Blair and Sarah Michelle Gellar making out for 47 seconds.
  • 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.
  • The Fool: 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 Playedfor Laughs. More than anything, she's simply naive and lacks social graces. She gets better; at the end of the film, she finally understands the other characters' true motivations and helps to take down Kathryn.
  • 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.
  • For the Evulz
    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.
  • French Jerk: Okay, technically Sebastian and Kathryn are French-Americans. But they're still jerks.
  • Freudian Couch: Sebastian lies on the couch in his therapist's office.
  • Freudian Excuse: 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?
  • 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?).
  • Genre Blindness:
    Annette: It amazes me someone as charming as you can be so manipulative.
  • 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.
  • 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.
  • Good Is Not Soft: 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.
  • Good People Have Good Sex: Sebastian and Annette's sex scene is depicted as tender and heartwarming in stark contrast to the other instances of sexual intercourse.
  • Good Smoking, Evil Smoking: Sebastian is an "evil smoker."
  • Grande Dame: Tiffany Merteuil uses her status in the community to persuade Nouveau Riche Social Climbers to "throw money" at her self-serving charity, as Kathryn puts it.
  • Hair of Gold, Heart of Gold: Beautiful young virgin Annette.
  • Hands-On Approach: Cecile and her music teacher Ronald, with a Cello.
  • 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. 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. However...
  • 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.
  • High School A.U.: Of Dangerous Liaisons.
  • Hollywood Homely: In Cruel Intentions 3, Patrick's Freudian Excuse for being a sexual predator is that he isn't fortunate enough to be an Adonis, especially in comparison to one male character who's played by a former Abercrombie & Fitch model. He even says he feels like he has to "play up the homely" with nerdy clothes and unstyled hair to trick girls into thinking he's a Nice Guy.
  • Hookers and Blow: Sebastian and Kathryn make drugs and debauchery look so glamorous.
  • 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.
  • Idle Rich: 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.
  • I'm Back: Sebastian tries to invoke this after breaking up with Annette, but he overdoes his performance and he's clearly been crying, so it's not all that convincing.
  • 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?
  • 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.
  • 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.
  • I Want You to Meet an Old Friend of Mine: Sebastian hands Kathryn a magazine that has Jennifer Love Hewitt on the cover. Both Ryan Phillippe and Sarah Michelle Gellar had starred alongside her in I Know What You Did Last Summer.
  • The Jeeves: Naturally, the Valmont house has a proper English butler to manage a full staff of diverse Ethnic Menial Labor stereotypes.
  • Jukebox Musical: The stage adaptation has classic 90s songs, from "Genie in a Bottle" to "No Scrubs" to "Only Happy When It Rains."
  • Kick the Son of a Bitch: 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.
  • Kid-anova: At 17, Sebastian is already "sick of sleeping with these insipid Manhattan debutantes."
  • Kissing Cousins/Twincest: The twins in the second movie claim to be Kissing Cousins, but were played by Real Life twins.
  • 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.
  • Ladykiller in Love: Sebastian, in 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?
  • Large Ham:
    • Cecile's mother, played by Christine Baranski.
  • 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: In the form of the rail-like Kathryn.
  • Light Feminine and Dark Feminine: Annette and Kathryn, respectively.
  • 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.
  • Love Is a Weakness: The movie's tagline is "In the game of seduction, there is only one rule: Never fall in love." Kathryn and Sebastian (at first) both live by this philosophy, which she uses as the basis for her "Reason You Suck" Speech against him.
  • Love Redeems: Sebastian, sort of. He comes clean about everything and sacrifices his life for Annette.
  • 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 Bastard: Sebastian and Kathryn both excel at manipulating people to their own advantage.
  • 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.
    • 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."
      • More irony in that St. Cecilia is the patroness of music. Cecile, by her own admission, is a Dreadful Musician.
  • Mr. Fanservice: Sebastian.
  • Nouveau Riche: The Caldwells in contrast to the Old Money Valmonts.
  • Noodle Incident: Cecile's mother about Sebastian: "I can't believe they didn't expel him after what he did to the school nurse."
  • 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.
  • Old Money: The Valmonts in contrast to the Nouveau Riche Caldwells.
  • The Omniscient Council of Vagueness: 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.
  • 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.
  • Operation: Jealousy: Kathryn tries this on Sebastian using Ronald, but it blows up in her face.
  • Panty Shot: Cecile Caldwell (Selma Blair) sitting on the couch with her legs open, giving a view of white panties under her khaki short skirt.
  • Pervert Dad: Although Sebastian's dad is certainly a sleazeball, in this case, it's actually Kathryn's mom who tries to get a little too close to her new stepson in the prequel.
  • Pet the Dog: Sebastian deliberately goes for this when volunteering to help Annette work at the old people home, with humorous results.
  • Police Are Useless: 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.
  • Practice Kiss: In a Les Yay 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.
  • Preacher's Kid: Swap preacher for headmaster. Annette is the headmaster's daughter and Daddy's little angel. Before Headmaster Hargrove takes over the position, Danielle Sherman is the same thing, only she's not what she seems.
  • 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 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 son, Bash Casey, once he comes out of the woodwork to claim his family name.
  • Prequel: Cruel Intentions 2... sort of. It was actually a pilot for a TV show that never happened.
  • Prison Rape: 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."
  • Psycho Ex-Girlfriend: Don't ever dump Kathryn if you know what's good for you. Furthermore, don't ever date her ex-boyfriends.
  • Racist Grandma: Cecile's mother, Mrs. Caldwell, seems like a cultured philanthropist but barely conceals her decidedly ignorant views, no doubt carried over from her generation.
  • Rape Is a Special Kind of Evil: In Cruel Intentions 3, Patrick becomes the official villain of the movie when he crosses this line.
  • Really Gets Around: 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.
  • "Reason You Suck" Speech: Kathryn gives one to Sebastian after she tricks him into dumping Annette.
    Kathryn: You were 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.
  • 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.
  • Reprise Medley: The musical has two.
    • The Act One closer, "Only Happy When It Rains," concludes with all the main characters singing reprises of nearly every song in the act.
    • 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, Tiffany and Cassidy Merteuil come 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.
  • Scatterbrained Senior: Since Adults Are Useless anyway, it should come as no surprise that the residents at the nursing home that Sebastian and Annette visit are adorably senile.
  • Screw the Rules, I Have Connections!: Cruel Intentions 2 invokes this trope often to explain how the characters are able to pull off some pretty 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.
  • 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 Circle of Secrets: Kathryn's many extracurricular activities include running the Manchester Tribunal, a secret society (if only Cecile knew) of cruel popular kids at her snobby prep school. Basically, it's a rip-off of the Skull and Bones fraternity at Yale. Orders of business include such dastardly plans as ruining classmates' reputations, getting faculty members fired and scoring tickets to the Hole concert.
  • 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.
  • Setting Update: Of Dangerous Liaisons. It takes it from 18th century France to 1990s New York City, changing all the characters to teenagers.
  • Seven Deadly Sins: Both Sebastian and Kathryn have this:
    • Both are incredibly promiscuous people. (Lust).
    • Both mostly sit around and so little work. (Sloth)
    • Both come from a wealthy background. (Greed)
    • Kathryn is a drug addict. (Gluttony)
    • Kathryn envies her classmates. (Envy)
    • Kathryn and Sebastian despise others around them. (Wrath)
  • Shower Scene: Cruel Intentions 2 has a shower scene with a pair of twins making out in front of Sebastian, which, incidentally, is the only thing people remember about the film.
  • Sinister Shades: 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 seducing Greenbaum's daughter to humiliate her. At the end, Annette's final scene (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.
  • Sissy Villain: Sebastian, who is symbolically emasculated not only by Kathrynnote , but also in a way by Cecilenote .
  • 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 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.
  • Social Climber: 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, Bunny Claymon has the exact same hopes for her daughter Cherie.
  • The Sociopath: Kathryn and Sebastian both have elements of this: superficial charm, sexual promiscuity, lack of meaningful relationships, manipulation of others...
  • Some of My Best Friends Are X: Cecile’s mom denies disapproving of Ronald dating Cecile because he’s black, citing the fact that she’s donated money to Colin Powell’s foundation. Ronald is duly impressed.
  • Sophisticated as Hell: Sebastian and Kathryn, being afforded the best education money can buy, mix phrases such as "au contraire" with adolescent potty-mouth language.
  • Spit-Trail Kiss: The infamous lesbian kiss between Kathryn and Cecile was like this.
  • Stealth Pun: 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 "slithers" seductively onto Sebastian's lap and hatches an evil plan.
    • Cecile wears a red hoodie when she sneaks out to go see Sebastian.
    • Kathryn's blue-and-silver bedroom is a rather obvious one (see Ice Queen 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 neck of the champagne bottle toward his face when he says he and Kathryn should celebrate was intentional.
    • The way Sebastian strokes the handle of his tennis racket when he taunts Cecile isn't so stealthy.
  • 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. The '90s teen counterpart, on the other hand, just comes off as pathetically emo and wangsty.
  • 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.
  • Teens Are Monsters: 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.
  • There Are No Adults: 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.
  • The Three Faces of Eve: The three girls: Annette (wise and mature) as the wife, Kathryn (cold, manipulative Femme Fatale) as the seductress and Cecile (sheltered Naïve Everygirl) as the child.
  • Token Minority: Subverted, as the minority characters are there for the sake of blatant political incorrectness. 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  and "fudge-packer" jokes.
  • Took a Level in Jerkass: Again, Cecile, who gets more bitchy and slutty as the film goes on, just as Kathryn had planned.
  • 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
  • Totally Radical: 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")
  • 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".
  • Unsuspectingly Soused: Becomes something of a running gag across the series.
  • Verbal Backspace: 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.
  • 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.
  • Villain Protagonist: Sebastian is the protagonist of the movie despite being a thoroughly horrible person, only becoming sympathetic toward the end.
  • 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...
  • 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.
  • Virginity Makes You Stupid: Subverted with Annette, played straight with Cecile. Not that Cecile is any smarter afterward.
  • 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?: Ronald is instantly smitten with Cecile as well as, as it turns out, 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, 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.
  • Wicked Stepmother: Kathryn's mother tells Sebastian in no uncertain terms that if he doesn't keep an eye on his philandering father, the two of them will both be kicked "out on the street."
  • 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.


Video Example(s):

Alternative Title(s): Cruel Intentions 2


Cruel Intentions- Colin Powell

How dare you accuse her of racism--she gave money to Colin Powell!

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